Chicago Private & Luxury Tours

Discover top private and luxury tours in Chicago, including architecture cruises, lake cruises, and exclusive sightseeing experiences tailored for you.

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2 Day Private Tour Chicago to Mackinac Island Exploration

Leave the city's hustle behind and embrace the tranquility of Mackinac Island, a destination where cars are absent, and the charm of horse-drawn carriages preva

From $2,700.00 USD

2 Hour Bridgeport /Stockyard Chicago Tour

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Bridgeport /Stockyard Tour, led by H

From $45.00 USD

2 Hour Bronzeville, Chicago Tour

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Bronzeville, led by Historian Dilla,

★ 5.0 (2)

From $45.00 USD

2 Hour Chatham, Chicago Tour

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Chatham, led by Historian Dilla, who

From $45.00 USD

2 Hour Englewood, Chicago Tour

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Englewood, led by Historian Dilla, w

From $45.00 USD

2 Hour North Lawndale, Chicago Tour

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like North Lawndale, led by Historian Dil

From $45.00 USD

2 Hour Pilsen and Little Village, Chicago Tour

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Pilsen, led by Historian Dilla, who

From $45.00 USD

2 Hour Pullman/Roseland Chicago Tour

Explore the vibrant neighborhoods of Chicago with engaging tours that delve into the rich history and culture of areas like Pullman, led by Historian Dilla, who

From $45.00 USD

2 Hours Chicago Architecture Tour - Skyscrapers and Photo Ops

Explore the architectural extravaganza of Chicago downtown and discover the most amazing and captivating facts about the first high-rises, city planning, and co

★ 5.0 (1)

From $89.00 USD

2 hours Private Evening Walking Tour with the Ghosts of Chicago

Step into the eerie past of Chicago on this thrilling 2-hour private ghost tour led by a local through the haunted corners of the Lincoln Park area.

From $350.00 USD

2-Hour Chicago's Chinatown History and Culture Tour

Discover the heart of Chicago’s Chinatown with your authentic history and culture tours, exclusively offered by the official Chinatown Visitor Center. Led by ex

★ 3.8 (5)

From $30.00 USD

360 CHICAGO Observation Deck & Hop-on Hop-off Sightseeing Tour

Explore Chicago at your own pace with a 48-hour hop-on hop-off bus tour, providing unlimited access to the city's iconic neighborhoods and landmarks. Relax on o

★ 4.2 (5)

From $84.00 USD

4 Hours of Chicago City Tour Sedan

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city

From $640.00 USD

4-Hour Chicago City Tour by SUV

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city

★ 5.0 (2)

From $800.00 USD

5-Day Tour of Superior, Huron and Michigan from Chicago

Five days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are located in Lake Michigan in t

★ 5.0 (3)

From $1,355.00 USD

90 minute Chicago's Chinatown History and Culture Tour

Explore the highlights of Chicago’s Chinatown in just 90 minutes with our expert-guided History and Culture Tour. This tour takes you through iconic landmarks,

From $30.00 USD

A Woman's Place: The Chicago Women's History Walking Tour

Forget the history you learned in school—Chicago’s story looks very different when told through the women who helped shape it. On this captivating 2-hour walkin

★ 5.0 (4)

From $35.00 USD

Art Institute of Chicago Private Expert Guided Tour

Let our expert local guides share their passion with you for The Art Institute of Chicago on this private 2 hour tour. As you traverse the hallowed halls, you’l

★ 5.0 (135)

From $215.00 USD

Art Institute of Chicago Skip-the-Line Exclusive Guided Tour

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour exclusive guide

★ 5.0 (364)

From $90.10 USD

Best of Chicago: Premium Small Group City Tour

Discover Chicago on a 2.5-hour premium small group city tour combining landmark architecture, public art, and lakefront scenery. Begin along the Magnificent Mil

★ 5.0 (46)

From $48.00 USD

Bike Tour in Chicago

Take a spin through the Windy City on a bike tour and discover the most remarkable and world-famous sights. Hit the streets like a local with your guide, dive i

From $129.00 USD

Bike Tour of Chicago's Lakefront Neighborhoods

This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excell

★ 4.9 (268)

From $59.00 USD

Bird Tours across Chicago

With over 10 years of birding, Wayne can not only identify birds out in the wild through sight, but also through their many calls! Interested in starting out wi

★ 5.0 (1)

From $60.00 USD

Bizarre Wicker Park: Medicine and Mobsters Self-Guided Audio Tour

This 45-minute self-guided walking tour explores the bizarre history beneath Wicker Park’s elegant surface. Led by a longtime resident, you will discover the ne

From $9.99 USD

Bucktown and Wicker Park’s 606 Trail: A Walking Tour

The Bloomingdale Trail was built on a former railway line that once served as the industrial backbone of Chicago's north side. On this self-guided audio tour th

From $5.00 USD

Burning Spirits Haunted Pub Crawl

Step into the shadows of Chicago’s past on this adults-only haunted pub crawl, where ghost stories, historic landmarks, and legendary nightlife collide. Beginn

★ 5.0 (1)

From $34.99 USD

Chicago 6-Hour City Tour by Sedan

Luxury vehicles Professional chauffeurs Updated fleet Licensed chauffeurs Knowledge about navigating in the city

★ 5.0 (2)

From $960.00 USD

Chicago Amazing Lakefront Bike Tour

Enjoy the car-free lakefront trail and explore Chicago’s beaches, parks, lagoons, This tour offers a diverse mix of nature and attractions. Top sights include:

★ 3.3 (9)

From $49.00 USD

Chicago and All MidWest Self Guided AI Audio Tours for 7 Days

With this AI app, you're no longer restricted to crowded group tours or rigid scripts. Explore iconic Chicago sites like Millennium Park and the Magnificent Mil

★ 5.0 (3)

From $11.39 USD

Chicago Architecture Center River Cruise aboard First Lady

The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chi

★ 4.9 (7641)

From $57.00 USD

Chicago Architecture Gilded Interiors Walking Tour

Visit the most beautiful interiors in Chicago with a local guide bringing their stories to life. Step into stunning centuries-old architecture on a guided wal

From $27.99 USD

Chicago Architecture River Cruise

Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of th

★ 4.8 (17211)

From $39.00 USD

Chicago Architecture River Tour & Hop-on Hop-off Sightseeing Tour

Save 20% when you bundle these two iconic Chicago experiences! Discover Chicago by road and river with a 48-hour Hop-on Hop-off Ticket and Shoreline Architect

★ 4.1 (53)

From $99.00 USD

Chicago Architecture Tour: Underground Pedway and the Loop

This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to the overall

★ 4.9 (593)

From $35.00 USD

Chicago Architecture Walking Tour: What's New

Over the course of 90 minutes, explore some of the newest buildings around the Chicago Architecture Center, focusing on construction elements and their impact o

★ 5.0 (91)

From $35.00 USD

Chicago Architecture, Art and History Tour - Off The Beaten Path

This short but sweet and unique adventure will take you on a 2-hour walking tour by the interiors of the most iconic buildings of Chicago downtown. Dive into t

From $95.00 USD

Chicago Architecture, History and Culture Loop Walking Tour

Explore Chicago’s historic Loop through the prism of its architecture. This three-hour trek will cover defining moments from 350 years of Chicago’s history, inc

★ 5.0 (4)

From $50.00 USD

Chicago Art Deco Madness Walking Tour

Chicago’s Loop is home to some of the city’s most perfectly preserved Art Deco architecture designed during the Roaring 20s. See 7 stunning Art Deco buildings,

★ 4.9 (33)

From $45.00 USD

Chicago Art Heist: Millennium Park Puzzle Adventure

You just stole Edward Hopper's Nighthawks from the Art Institute of Chicago. Now you need to disappear into the city before anyone notices. This self-guided esc

★ 3.9 (11)

From $8.01 USD

Chicago Audio Guided Walking Tour 3h and 25 Audio Commentaries

Chicago, a city with undeniable charm, awaits you for a walking exploration of its 25 must-see attractions. From the Riverwalk to Marina City to the famous Clou

From $7.32 USD

Chicago Chinatown: Dragon Kings Puzzle Adventure

The year is 1375, and a devastating drought grips China. The Emperor sends you, his Imperial Advisor, to find the four Dragon Kings, rulers of weather and water

★ 3.8 (10)

From $7.97 USD

Chicago City Private Tours

Ready to explore Chicago like never before? Whether you have just a couple of hours or a full day, my personalized city tours offer a unique and unforgettable e

★ 4.6 (38)

From $199.00 USD

Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and

★ 4.8 (103)

From $35.00 USD

Chicago City Tours See It All No Time Wasted

Skip the corny jokes and never-ending speeches — our shared tours are built for travelers who want the real Chicago, not a stand-up routine. ✔️ Over 20 iconic

★ 3.8 (21)

From $150.00 USD

Chicago City's Iconic Sights and Suburb Gems Tour

This tour offers a refreshing blend of Chicago’s iconic sights and hidden suburban gems, giving travelers a unique perspective on the city's diverse culture, hi

From $299.00 USD

Chicago Crime and Mob Bus Tour

Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great phot

★ 4.6 (3638)

From $49.00 USD

Chicago Crime, Mobsters & Ghosts Walking Tour

Join us along the historic streets and alleys of Chicago as we walk among the spirits of mobsters and ghosts of the condemned. This tour is for lovers of histo

★ 4.7 (474)

From $34.00 USD

Chicago Custom Private Walking Tour with A Guide ( Private Tour )

Chicago can sometimes feel inaccessible to visitors, but a private walking tour with a local guide takes the mystery out of the city. This personalized tour foc

From $126.08 USD

Chicago Downtown Private Guided Walking Tour

Uncover Chicago’s bold spirit through its iconic landmarks, from the Gothic Holy Name Cathedral to the gleaming Cloud Gate. Hear untold stories of resilience, a

From $205.00 USD

Chicago Downtown Sports History Tour - An App-Guided Adventure

Uncover the essence of Chicago's sports culture on this guided tour through the downtown area. Learn about the city’s iconic sports figures, explore fascinating

From $5.00 USD

Chicago Downtown TV and Movie Sites Private 2-Hour Walking Tour

Explore over 30 iconic movie and TV locations on this two-hour walking tour of downtown Chicago! Visit sites from Ferris Bueller’s Day Off, The Untouchables, Th

★ 4.8 (4)

From $130.50 USD

Chicago Downtown Walking Tour & Lake Michigan Cruise Tickets

Walk beneath Chicago’s soaring skyline, hear its hidden stories, then see it shimmer from the water on a lake cruise. From the iconic Bean to the legendary thea

From $263.00 USD

Chicago Early Skyscraper Walking Tour in the Loop

Step into the birthplace of the modern skyscraper on this immersive walking tour through Chicago’s historic Loop. Discover the stories, innovations, and hidden

From $39.00 USD

Chicago Exotic Auto Experience

This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests e

From $1,800.00 USD

Chicago Family Food and Bike Tour with Top Attractions

This Chicago Food & Bike tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past year have ranked as Top 10 in Ame

★ 4.8 (101)

From $79.00 USD

Chicago Favorites Ultimate Food and Walking Tour

The perfect Food Tour of Chicago for first timers or anyone eager to explore Chicago's famous foods & top attractions—all in one tour. Stroll the beautiful stre

★ 4.9 (2404)

From $84.99 USD

Chicago Fire TV Show Set Tour

Get an exclusive behind-the-scenes look at the hit NBC drama Chicago Fire TV Show Set Tour. Visit the actual filming locations where the show comes to life. T

★ 4.9 (80)

From $315.00 USD

Chicago Fireboat Fireworks Cruise

Enjoy an unforgettable evening on Lake Michigan with the Chicago Fireworks Cruise. Witness the stunning skyline as you glide across the water, leading up to the

★ 4.5 (19)

From $63.13 USD

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all the city'

★ 4.9 (1054)

From $84.99 USD

Chicago Foods Tour with The Loop, Skyline, Millennium Park

Delve into Chicago’s one-of-a-kind cuisine and learn something that you would never expect on this small-group Secret Food Tour. Eat your way through the most p

★ 4.6 (5)

From $145.00 USD

Chicago Full-Day Walking Food Tour with Free Bike or Kayak Rental

Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary flavors

★ 5.0 (3)

From $99.00 USD

Chicago Gangster History Walking Tour of River North

Go beyond Capone. An expert guides uncovers the Beer Wars, the ambushes, and the brutal rivalries on these exact streets.

★ 4.8 (4)

From $39.99 USD

Chicago Gangsters and Ghosts Minibus Tour

Uncover the notorious history of Chicago's gangster era on this immersive bus tour that takes you through the city's most infamous landmarks. Visit the Palmer H

★ 4.9 (16)

From $65.00 USD

Chicago Gangsters and Ghosts Walking Tour

We are the original, top-rated Gangsters and Ghosts tour! Hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop distr

★ 4.8 (330)

From $38.00 USD

Chicago Gangsters and Ghosts Walking Tour

We are the original, top-rated Gangsters and Ghosts tour! As a private tour, hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chica

From $186.00 USD

Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour

Explore haunted Chicago at your own pace and schedule. Go anytime. Why take this tour? -It's like an in person tour guide, only it's on your phone. -Tour at y

★ 4.8 (6)

From $9.75 USD

Chicago Haunted Interior Architecture Ghost Tour

Take the best ghost tour in Chicago! Go inside 6/8 old buildings, learn about what makes them haunted and what also makes them cool! Learn from expert guides wh

★ 5.0 (26)

From $35.00 USD

Chicago Hauntings Original Ghost Walk through Old Chicago

We wrote the book(s) on Chicago ghosts! Now in our 26th year! Ursula Bielski, our founder, has published more than a dozen volumes on Chicago's haunted history

★ 5.0 (1)

From $40.00 USD

Chicago Haunts and Hooligans Tour

Nightly Spirits’ Haunts and Hooligans Tour will illustrate Chicago’s haunted history of secret parlors, underground tunnels, murderous movie theaters and supern

★ 5.0 (42)

From $34.77 USD

Chicago Helicopter Tour: City to Shoreline

Your journey begins with a southeast departure from the Vertiport, offering early views of the city’s iconic skyline. Flying east, you’ll head toward the lakefr

★ 4.5 (35)

From $349.99 USD

Chicago Helicopter Tour: Loop Tour

Take to the skies and experience Chicago from an entirely new perspective on this extended helicopter tour showcasing the city’s most iconic landmarks, neighbor

★ 4.3 (23)

From $209.99 USD

Chicago Highlights Private Walking Tour with a Guide

Immerse yourself in Chicago's architectural heritage on an exclusive walking tour, delving into the city's iconic structures and Art Deco gems. Begin your intim

★ 5.0 (2)

From $125.45 USD

Chicago Highlights Running Tour

Join us for the most memorable experience you will have while visiting Chicago! For runners from around the world, this is definitely a “bucket list” activity.

★ 5.0 (1)

From $44.00 USD

Chicago Hop-on Hop-off Sightseeing Tour by Open-top Bus

Discover Chicago at your own pace with Big Bus. Travel aboard an open-top, double-decker bus and enjoy panoramic views of the city's most famous landmarks, incl

★ 3.9 (2445)

From $49.00 USD

Chicago in Spanish. Architecture. Mafia, Interiors, Underground

Discover the real Chicago with those who really know it! At ChicaGo Turismo we transform a simple tour into an unforgettable experience. More than visiting mon

★ 5.0 (11)

From $45.00 USD

Chicago Insider Segway Tour

This is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the totally weird stories of Chica

★ 4.9 (52)

From $72.00 USD

Chicago Jewish History Landmarks Private Guided Walking Tour

Walk through Chicago’s vibrant Jewish history, from the striking Loop Synagogue to the inspiring Heald Square Monument and Jay Pritzker Pavilion. Uncover hidden

From $227.00 USD

Chicago Lake and River Architecture Tour

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years of fascinating soc

★ 4.7 (2492)

From $48.00 USD

Chicago Lakefront Electric Bike Tour

This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will get a c

★ 4.6 (18)

From $69.34 USD

Chicago Lakefront Trail: A Self-Guided Bike Tour

This self-guided bike tour traces Chicago's reinvention from the ashes of the Great Fire to the skyline that rose in its place, pedaling the Lakefront Trail wit

From $14.99 USD

Chicago Local Brewery Expedition with Homemade Guacamole

We'll explore five (5) of our favorite, Handcrafted Local Micro Breweries in two special locations of the historic, Chicago landmark district, Fulton Market; wh

★ 5.0 (4)

From $63.00 USD

Chicago Local Fashion Designers Shopping Tour with a Stylist

Discover the local shopping scene and its fashion DNA with a professional stylist as you embark on a personalized shopping circuit built to meet your style and

From $149.89 USD

Chicago Loop Food Tour: Taste the Most Iconic Local Eats

Join a local guide for the ultimate foodie adventure in Chicago’s historic Loop, tasting classics like deep‑dish pizza and Chicago‑style hot dogs while discover

★ 4.8 (134)

From $131.55 USD

Chicago Loop Self Guided Ghosts Gangsters and Secrets Tour

Downtown Chicago has a dark history hiding in plain sight. This self-guided audio tour takes you through the Loop on your own schedule, with narration on your p

From $20.00 USD

Chicago Loop Self-Guided Audio Tour: Architecture & History Walk

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown. This journey unveils a blend of striking skysc

★ 5.0 (5)

From $9.99 USD

Chicago Loop Walking Tour

The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists

★ 4.9 (57)

From $60.00 USD

Chicago Millennium Park Self-Guided Walking Tour

Enjoy moving at your own pace through Chicago's Millennium Park with an app as your guide. You and your private party can stop or start the app whenever you lik

★ 4.6 (5)

From $12.74 USD

Chicago Milwaukee and Lakes 6 Day Tour

Six days to enjoy the beautiful scenery of the three major lakes in the Great Lakes region of the United States, all of which are located in Lake Michigan in th

From $1,387.00 USD

Chicago Movie Locations Tour

Discover iconic Chicago movie locations with a private tour, including transportation and hotel pickup and drop-off. Visit the Home Alone house exterior, Wrigle

★ 5.0 (11)

From $315.00 USD

Chicago Murder Mystery Tour

You will solve a murder as you learn real Chicago history! Play detective as you unravel a murder mystery, and learn about Chicago's true crime legends and Proh

★ 5.0 (759)

From $35.00 USD

Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s Whodunit

Channel your inner Sherlock Holmes in this murder mystery hunt around The Chicago Loop. In the “Murder in The Chicago Loop” transports you to the year 1923.

★ 5.0 (1)

From $59.00 USD

Chicago Night Crimes Tour by Bus

Join us for a fun night of exploring Chicago's crime history on this 2-2.5-hour bus tour that includes: * World famous crime scenes like the St Valentine's Day

★ 4.8 (524)

From $55.00 USD

Chicago P.D. TV Show Set Tour

Get an exclusive behind-the-scenes look at the hit NBC drama Chicago P.D. TV Show Set Tour. Visit the actual filming locations where the show comes to life. T

★ 5.0 (34)

From $315.00 USD

Chicago Photo Capture Your Adventure Walking Tour

Discover Chicago's iconic sights on this guided walking tour that highlights five scenic photo spots. With a local guide, enjoy stunning skyline views and learn

★ 5.0 (1)

From $49.00 USD

Chicago Pizza Tour

Enjoy Chicago’s only bus guided neighborhood pizza tour. Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza.

★ 4.9 (489)

From $89.00 USD

Chicago Pope Leo XIV's Roots Tour

Discover the unique journey of Pope Leo XIV through Chicago on this interactive bus tour. Visit his childhood home and childhood church in the suburb of Dolton

From $79.00 USD

Chicago Private Custom City Tour with Hotel Pick Up

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS. Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago.

★ 4.9 (211)

From $539.00 USD

Chicago Private Lakefront Sunset and Skyline Photo Tour

Enjoy a private, fully personalized sunset tour along Chicago’s scenic lakefront. Travel in comfort with your English-speaking driver, who shares insights into

From $111.18 USD

Chicago Private Neighborhoods Tour to Lincoln and Hyde Park

Discover the vibrant neighborhoods and cultural districts of Chicago on a private, fully personalized tour. Travel in comfort with your English-speaking driver,

★ 5.0 (1)

From $216.69 USD

Chicago Private Night Skyline and Lakefront Scenic Tour

Experience Chicago’s glowing skyline and scenic lakefront on a private, fully personalized night tour. Travel in comfort with your English-speaking driver, who

★ 3.0 (2)

From $94.50 USD

Chicago Private SightSeeing Tour

See Chicago’s most iconic sights, hear the stories behind the city, and enjoy a comfortable sightseeing experience without the stress of navigating traffic or p

From $89.00 USD

Chicago Private Tour

Enjoy and appreciate Chicago with your private transportation and guide. Customize your tour and visit the most important sites and landmarks of the Windy City.

From $300.00 USD

Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens

Discover the natural beauty of Lake Geneva and the tranquil Anderson Japanese Gardens on this private 10‑hour getaway from Chicago. Begin your day with convenie

From $1,200.00 USD

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introdu

★ 4.6 (3778)

From $28.00 USD

Chicago River 90 Minute Architecture Tour

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic lega

★ 4.7 (11316)

From $45.00 USD

Chicago River Fireworks Cruise

Enjoy the Navy Pier Fireworks from the Chicago River. A brief version of Wendella's Lake Michigan Fireworks Cruise, this experience is 45 minutes and does not g

★ 3.3 (3)

From $32.00 USD

Chicago River Floating Tiki Bar Cruise Friday and Saturday

Set sail for an unforgettable evening aboard the River Star or Island Time, where the drinks are flowing and the views are unmatched. Enjoy a refreshing beverag

★ 4.8 (27)

From $42.00 USD

Chicago River Spectacular Fireworks Show and Tiki Bar Cruise

Fireworks Cruise Aboard Island Time – See the Sparks Fly the Island Party Way! Experience Chicago’s dazzling fireworks like never before—from the deck of our f

★ 4.1 (40)

From $54.00 USD

Chicago River Tiki Bar Party Cruise from Chicago River Wednesdays

See Chicago the Island Party Way. Our floating Tiki Bar offers you the opportunity to take in all the sights and sounds as you relax and enjoy a beverage. Have

★ 4.0 (129)

From $43.00 USD

Chicago River Yoga Walk Tour

This is truly an experience like none other. It is combination of a historical walking tour of the Chicago Riverwalk and Yoga. It is a very non-traditional Yoga

From $44.00 USD

Chicago Riverwalk Architecture Walking Tour

Explore Chicago's iconic skyline on this enlightening Riverwalk architectural tour. Experience the rich tapestry of history and innovation as "you get your step

From $49.00 USD

Chicago Riverwalk Self-Guided Walking Tour

Welcome to Chicago’s scenic Riverwalk. Spanning from Lake Michigan west to Franklin Street. Called the city second Lakefront', the Riverwalk contains restaurant

★ 4.1 (9)

From $12.74 USD

Chicago Scenic Driving Tour

Chicago is a big city with a lot of activities & sightseeing. To tour the city quickly, it requires the help of a knowledgeable local driving guide and that's w

★ 5.0 (24)

From $315.00 USD

Chicago Seadog River & Lake Architectural Tour

Soak in unobstructed views of Chicago’s world-famous architecture from the water with an exciting ride on our Seadog River and Lake Architectural Tour! Sail thr

★ 4.5 (317)

From $42.84 USD

Chicago Seasonal Stroll Walking Tour of Holiday Attractions

There’s nothing more magical than Christmas in Chicago, & this 2hr guided Chicago Walking Tour takes you straight into the heart of it. Journey through the Chic

★ 5.0 (5)

From $44.99 USD

Chicago Self-Guided Audio Tour

Discover Chicago like never before with complete freedom to explore at your own rhythm, lingering at fascinating locations or moving swiftly through others as y

★ 3.9 (9)

From $6.00 USD

Chicago Shoreline Adventure Boat Tour

This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military Williard Marine, which prov

★ 5.0 (40)

From $90.00 USD

Chicago Skyline Snap Tour Helicopter Flight Over Chicago

Witness Chicago’s stunning skyline from above on this exhilarating helicopter tour. Departing from the Vertiport, the flight offers breathtaking views of the ci

★ 3.8 (31)

From $149.99 USD

Chicago Small Group City Tour

Experience Chicago like never before on your all-inclusive small group city tour, led by an expert guide. Discover iconic landmarks, hidden gems, and vibrant ne

★ 5.0 (1)

From $465.00 USD

Chicago Street Art and Creative Districts Tour

Explore Chicago’s vibrant street art and creative neighborhoods on a private, fully personalized tour. Travel in comfort with your English-speaking driver, who

From $108.89 USD

Chicago Suburbs Hidden Gems: Small-Group Exploration Tour

Experience a global adventure without leaving Chicagoland! This tour blends rich cultural landmarks, stunning natural beauty, and nostalgic favorites, creating

★ 4.4 (7)

From $269.00 USD

Chicago Suburbs Movie Sites Private Tour

Discover Hollywood magic in the heart of the Midwest on the Chicago Suburbs Movie Sites Tour. Visit real filming locations from classics like Ferris Bueller’s D

From $270.00 USD

Chicago Sunset Segway Tour

Ease into the evening with a relaxing glide through the parks and lakefront in Chicago. This evening ride offers cooler temperatures and beautiful sunset views

★ 4.9 (28)

From $75.00 USD

Chicago to Mackinac Island Scenic Tour

Explore the charm of Mackinac Island on this delightful journey from Chicago. Experience a blend of history, culture, and stunning landscapes as you travel thro

From $685.00 USD

Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights

Escape Chicago for a day and experience Milwaukee’s culture, food, and legendary beer scene. This curated day trip includes highlights such as the Harley-Davids

★ 4.4 (13)

From $125.00 USD

Chicago to Washington D.C. Cherry Blossom 3-Day Tour

Celebrate the beauty of spring and the rich history of the National Cherry Blossom Festival, commemorating the 1912 gift of 3,000 cherry trees from Tokyo to Was

From $496.00 USD

Chicago Tour South Side

The Blue-Collar side of Chicago many call it! This tour will show The Ford Factory, home of the steel mills, the blue-collar neighborhoods and many places on th

★ 4.5 (50)

From $125.00 USD

Chicago VIP Private Tour

Discover the very best of New York City in one unforgettable experience! From the majestic Statue of Liberty and the historic Brooklyn Bridge to famous neighbor

From $499.00 USD

Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking Tour. D

★ 5.0 (7)

From $49.99 USD

Chicago Walking Tour: A Walk Through Time

Want a quick introduction to Chicago’s magnificent architecture? This 90-minute tour takes a comprehensive look at the city’s architectural history by viewing b

★ 4.9 (233)

From $35.00 USD

Chicago Walking Tour: Art Deco Skyscrapers Loop

View Art Deco masterpieces built in the heart of Chicago’s financial district during the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimis

★ 4.8 (199)

From $35.00 USD

Chicago Walking Tour: Connecting Past and Present

This lively overview of Chicago architecture explores iconic buildings from the 1890s to present. We'll compare and contrast a wide range of buildings with vary

★ 5.0 (44)

From $35.00 USD

Chicago Walking Tour: Historic Skyscrapers

Chicago is home to some of the world’s earliest skyscrapers. Get an up-close look at these 19th Century marvels, learn about innovations used to build them and

★ 4.8 (81)

From $35.00 USD

Chicago Walking Tour: Historic Treasures of Chicago

Learn about the great architectural landmarks of Michigan Avenue and State Street. The 40 years between 1890 and 1930 saw the creation of some of Chicago’s the

★ 4.9 (462)

From $35.00 USD

Chicago Walking Tour: Modern Architecture

Looking for iconic Mid-Century Modern architecture? What better place than Chicago with its triumvirate of modern architects (Mies van der Rohe, Bertrand Goldbe

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From $35.00 USD

Chicago Walking Tour: The Magnificent Mile

Discover how a dirt road known as Pine Street transformed into a "Paris on the Prairie" and later into the Magnificent Mile, the city’s premier shopping distric

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From $35.00 USD

Chicago Walking Tour: Tiffany Treasures

Learn about the life and work of Louis Comfort Tiffany as we visit some of Chicago’s most magnificent art-glass and mosaic installations, each designed and craf

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From $35.00 USD

Chicago West Loop Sweet Treats Food Tour: Donuts, Cookies, & More

We begin at a local shop synonymous for their quality donuts––Do-Rite Donuts. From there we’ll walk the Randolph corridor, learning about the history of Chicago

★ 5.0 (94)

From $70.00 USD

Chicago's Chinatown Food and Walking Tour

Chicago's Chinatown: Few neighborhoods in America combine such delicious cuisine with fascinating history. Join Bobby’s Bike Hike & Food Tours, whose food tours

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Chicago's Delicious Downtown Donut Tour with 8 Amazing Tastings

Recently voted one of TripAdvisor's top food tours in the US. Discover the sweet side of the Windy City on the Underground Donut Tour, Chicago’s Delicious Don

★ 4.9 (1560)

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Chicago's Fireworks Show aboard Tall Ship Windy!

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats

★ 4.7 (26)

From $113.73 USD

Chicago's Gold Coast Hidden History: A Self-Guided Audio Tour

Where did Chicago’s millionaires live, love and misbehave? Walk the Gold Coast with historian Amy Bizzarri, author of 111 Places in Chicago That You Must Not Mi

★ 4.4 (8)

From $8.99 USD

Chicago's Original Gangster Tour by Bus

Our guides present an accurate account of the activities in Chicago during the 1920's and 1930's (Prohibition Era). You will hear about the exploits of Capone,

★ 4.6 (191)

From $48.00 USD

Chicago's Secret Interiors Architectural Walking Tour

We invite you to step inside the city’s most exclusive, jaw-dropping architectural treasures. Led by an expert local storyteller, you’ll discover breathtaking h

★ 4.9 (99)

From $35.00 USD

Chicago's Ultimate City Bike Tour of Top Downtown Attractions

Get acquainted with Chicago’s most iconic landmarks on this riotous guided Chicago bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-

★ 4.9 (280)

From $59.00 USD

Chicago's West Side Foodie Ride Bike Tour

Take a detour off the beaten path, and explore the flavors of Chicago’s delicious West Side with Bobbys's Bike Hike & Food Tours, America's longest running city

★ 4.9 (114)

From $99.00 USD

Chicago, Cloud Gate, Grant Park Full-Day City Tour

Discover Chicago, a vibrant city set along the shores of Lake Michigan, known for its world-class architecture, iconic skyline, and rich cultural scene. As the

★ 4.0 (4)

From $194.00 USD

Chicago-Milwaukee Small Group Tour

Discover the charm of Milwaukee on a small group day trip from Chicago! Enjoy a guided city tour, explore iconic landmarks, and experience the legendary Miller

From $485.00 USD

Chicago-Style Holiday Hike: Festive Food and Walking Tour

There’s nothing more magical than downtown Chicago during the holidays. Bobby’s Bike Hike & Food Tours—internationally recognized for quality—presents the Holid

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From $84.99 USD

Chicago: Gangsters and Food Tasting Walking Tour

Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious neighborhoods. Learn about Chicago's

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From $79.99 USD

Chicago’s Millennium Park Self Guided Audio GPS Walking Tour

Our tour will take you through Millennium Park, starting at the Millennium Park Welcome Center. We’ll wander past shining sculptures, playful fountains, and pea

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Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

See Chicago through the eyes of Al Capone and the Everleigh Sisters at your own pace with this affordable walking tour. • Walk in the footsteps of the gangster

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Chinatown Food Tour

Experience the authentic flavors of Chinatown on a 3-hour guided food tour curated by Chicago Tribune Good Eating Award winner Z.J. Tong. As you explore the nei

★ 5.0 (1)

From $98.00 USD

Chinatown History and Culture Tour

Winner of 10 Best History Tours by USA Today in 2026, and the "ORIGINAL" Chinatown tour since 2001. Discover the history, culture, and hidden stories of Chica

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Christmas Eve Plated Dinner Cruise on Lake Michigan

Celebrate the magic of the season on the water with a Christmas Eve Premier Dinner Cruise in Washington DC. You and your guests will enjoy a holiday 3-course, p

From $148.98 USD

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

Enjoy a picturesque day dining on Lake Michigan with our Premier Chicago Brunch Cruise. You’ll indulge in a chef-prepared buffet meal featuring savory and sweet

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From $120.28 USD

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Sail along the magnificent skyline on our Premier Plus Chicago Brunch Cruise. A chef-curated menu of plated brunch specials will delight your palate while unpar

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From $84.74 USD

City Cruises Chicago: River Architectural Lunch Cruise

Fine dining and unrivaled skyline views await from the moment you step aboard our Premier Plus Chicago Lunch Cruise. A selection of delectable plated lunch spec

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From $92.94 USD

City Cruises Chicago: Signature Brunch Cruise on Lake Michigan

Set sail for a memorable experience on Lake Michigan with a Signature Chicago Brunch Cruise that is as scenic as it is delicious! You'll savor a chef-prepared b

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From $99.78 USD

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

Join us for an unforgettable afternoon on Lake Michigan with a Signature Chicago Lunch Cruise. Whether it’s a family outing or a meal with friends, upgrade your

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Classic Chicago Food Lovers Tour in River North

Get a taste of Chicago on this small-group walking food tour and explore the specialties of River North neighborhood. Dive deeper into the culinary history of t

From $229.00 USD

Continental US Train Zephyr Adventure CA -CO - Il

Embark on the adventure of a lifetime! Step aboard the iconic California-Chicago Train Expedition as we whisk you away on a journey that combines the thrill of

★ 3.5 (2)

From $5.00 USD

Custom Chicago Walking Tours

We create custom walking tours for groups of all sizes and interests, blending delicious food experiences with rich historical storytelling. From downtown explo

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From $75.00 USD

Dark Tales of Bucktown: A Self-Guided Chicago Tour

Bucktown has a knack for keeping secrets - and most of them are deeply unsettling. On this self-guided walking tour, you'll hear the true stories behind the nei

From $11.99 USD

Downtown Chicago City Tour In a Lamborghini[60 Minute Experience]

Experience Chicago in unparalleled style with a 10-mile cruise through the city in a luxury or exotic vehicle. Glide through iconic streets, turning heads at ev

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From $99.00 USD

Downtown Chicago City Tour in a Rolls Royce[60 Minute Experience]

Your private luxury tour experience begins with a prompt pickup in downtown Chicago. Step inside the climate-controlled cabin of a world-class Rolls-Royce. Your

From $195.00 USD

Downtown Chicago City Tour in a Super Car [30 Minute Experience]

Turn heads and take in the views with your Premier Chicago Tour Experience! Your journey begins in the passenger seat of an automotive masterpiece. Tour downt

From $160.00 USD

Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. This 2.

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Downtown Chicago Loop Walking Tour (Private)

Discover the stories, styles, and spirit that built Chicago into the architectural capital of the world. On this walking tour through the Loop, you’ll explore t

From $27.00 USD

Downtown Chicago TV and Movie Sites Guided Walking Tour

Explore downtown Chicago through the lens of film and television on this guided walking tour featuring iconic filming locations from Ferris Bueller’s Day Off, T

★ 4.3 (25)

From $45.00 USD

Downtown Chicago Walking Pizza Tour

This tour is just a short walk through great Chicago neighborhoods starting near Navy Pier and the Magnificent Mile, and then heading into the Gold Coast & Rive

★ 5.0 (131)

From $69.00 USD

Electric Bike Tours in Lincoln Park

Discover the streets of Lincoln Park, Chicago, and the Magnificent Lake Front on a high-quality electric bike rental from E-Z Rider Bike Shop. Our e-bikes provi

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Embers of the Windy City: Chilling Chicago Ghost Tours

Come on our chilling ghost tour presented by US Ghost Adventures! Book Directly With Windy City Ghosts and save $5/person. Windy City Ghosts walking Ghost Tour

★ 4.5 (139)

From $26.00 USD

Exclusive Downtown Chicago Guided Walking Tour 12ppl Max

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. Tour Ch

From $55.00 USD

Explore Chicago Black Culinary Heritage

The Experience is more than a food tour. It is an immersive cultural experience that combines food, history, architecture, and storytelling in one of Chicago’s

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From $75.00 USD

Explore Chicago’s Indoor Mushroom Farm Experience

Step inside a unique and fascinating journey through Chicago’s premier indoor mushroom farm, as seen on FX/Hulu’s acclaimed series "The Bear," where our mushroo

★ 4.8 (5)

From $20.00 USD

Explore the Historic Old Post Office in Chicago

Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused into a beautiful, modern Class A Office building. It once

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From $15.00 USD

Express Chicago Photo Tour of Landmarks

Let’s take photos at one of Chicago’s most famous spots - the bright red CHICAGO sign at the Chicago Theatre! During this 30-40 minute photo walk, I’ll help you

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From $99.00 USD

Field Museum of Natural History Chicago Tour with Tickets

Skip the lines and uncover ancient wonders at Chicago’s Field Museum, home to SUE, the world’s most complete T. rex. Marvel at dazzling artifacts, real mummies,

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From $313.00 USD

Frank Lloyd Wright Oak Park Architecture Tour from Chicago

Explore the architectural genius of Frank Lloyd Wright on a private, fully personalized tour in Chicago, home to the world’s largest collection of his buildings

★ 4.4 (10)

From $217.78 USD

Frank Lloyd Wright Robie House Admission

The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture. This

★ 4.2 (169)

From $27.00 USD

Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective ri

★ 5.0 (1)

From $179.00 USD

Great Lakes & Mackinac Island 4-Day Small Group Tour from Chicago

Take in three of the Great Lakes and a string of classic Midwest towns on this four-day small-group loop out of Chicago. Travel up the western shore of Lake Mic

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From $1,132.00 USD

Great Smoky Mountains,Gatlinburg 4-Day Tour from Chicago

1. Explore Motorsports Hall of Fame. 2. Be in the National Park with most visitors in US -- Great Smoky Mountains. 3. Southern dinner show Dixie Stampede feat

From $1,030.00 USD

Happy Hour Fireboat Cruise

Take part in a unique evening Happy Hour Cruise, featuring fresh craft beers while cruising the stunning Chicago skyline. Every Thursday and Friday evening, thi

★ 5.0 (2)

From $52.00 USD

Haunted Chicago Booze and Boos Ghost Walking Tour

Join this Chicago haunted pub tour which is a combination ghost tour and pub crawl that will take you on a walking tour to explore the fascinating history of Ch

★ 4.9 (350)

From $35.87 USD

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Walk in the footsteps of Al Capone, John Dillinger, and real life ghost stories while hearing tales of Chicago's haunted past. Visit Prohibition Era speakeasy b

★ 5.0 (488)

From $35.00 USD

Haunted Chicago: Lincoln Park Ghost & History Walking Tour

This isn’t just a ghost tour, it’s a story-driven walk through one of Chicago’s most haunted landscapes, where real history and local legend collide. Unlike to

★ 4.1 (14)

From $29.99 USD

Haunted Chicago: Lincoln Park Ghost Escape Game

A dating app. A stranger with arctic blue eyes. A meeting in Lincoln Park on Halloween. This self-guided ghost escape game drops you into Chicago's most haunted

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From $7.97 USD

Haunted Ghosts & The Chicago Outfit Segway Tour

Looking for a unique Chicago tour? Glide into the city’s dark past with our unique Segway tour, where ghosts, gangsters, and true crime come to life. Cruise to

★ 4.7 (38)

From $75.48 USD

Historic Homes and Cottages of Wicker Park Walking Tour

Much of the historical information shared on this tour is unknown to most attendees. This tour also shows everything from the gritty to the pretty, from the mun

★ 5.0 (52)

From $45.00 USD

Historic Pullman Private Half-Day Walking Tour

Step into Chicago’s past and explore the story of America’s first model industrial town on this guided walking tour through the Pullman Historic District. Once

From $223.00 USD

Historical and Architectural Chicago Fireboat River & Lake Cruise

Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel on Lake Michigan and through the Chicago River seeing the sights.

★ 4.9 (514)

From $38.76 USD

History and Architecture of Chicago Loop Walking Tour

Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walk among gigantic towers of downtown and learn how Chicago became

★ 5.0 (31)

From $33.00 USD

History of the Jazz Age at Chicago Art Deco Architecture Tour

Dive into the center of the architectural boom of the roaring 1920s and take a chance to enjoy the grand facades of the Art Deco skyscrapers on this guided walk

From $67.00 USD

Holiday Lights Tour Chicago BYOB on a Double Decker

Explore the festive charm of Chicago during the holiday season on a double-decker bus tour showcasing the city's dazzling lights. This BYOB tour allows you to s

From $40.00 USD

Hyde Park Walking Tour History Race and Urban Change

Discover the rich history and dynamic transformation of Hyde Park on this engaging walking tour. Delve into the neighborhood's evolution from a lakeside retreat

From $5.00 USD

Iconic Action Film and Movie Locations 1 Day Tour in Chicago

From the Gotham chaos in The Dark Knight to the explosive battles of Transformers, Chicago’s skyline has played a starring role in countless blockbusters. On to

★ 5.0 (3)

From $158.00 USD

Intro to Chicago Architecture

Immerse yourself in the fascinating history of how a muddy Midwestern outpost transformed into the global capital of architecture. Experience everything from ea

★ 5.0 (30)

From $35.00 USD

Journey of the Chicago Flag Bus Tour

This family friendly tour uncovers the powerful legacy behind Fort Dearborn, the devestation of the Great Chicago Fire, and the re-birth tied to the World's Col

From $42.00 USD

Lake Michigan 30 Minute Speedboat Ride

Enjoy Chicago’s iconic skyline with an exciting speedboat Tour on Lake Michigan. Departing from Navy Pier, the Lakefront Speedboat Tour is the best way to view

★ 4.1 (360)

From $45.16 USD

Lake Michigan Skyline Cruise in Chicago

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions. Cruise along Lake Michigan and enjoy st

★ 4.4 (956)

From $30.00 USD

Lake Michigan Sunset Cruise in Chicago

The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. The Cruise will navigate from the Chicag

★ 4.5 (1735)

From $48.00 USD

Lakefront Segway Tour in Chicago

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have

★ 4.6 (151)

From $70.00 USD

Lincoln Park Hauntings Ghost Investigation Tour

We are Chicago's only paranormal investigation tour, and Chicago's oldest ghost and hauntings tours, founded by Ursula Bielski, Chicago's 35 year paranormal res

★ 4.9 (47)

From $43.99 USD

Lincoln Park Secrets: Private Enchanted Pedicab History Tour

Our knowledgeable and licensed guide will drive you between each location in an open air motorized pedicab! Also a great option for anyone with mobility impairm

★ 5.0 (1)

From $125.00 USD

Lincoln Park Zoo & Nature Museum Private Tour

Cover three Lincoln Park stops on a private walking tour through Chicago: the Peggy Notebaert Nature Museum, Lincoln Park Conservatory, and Lincoln Park Zoo. At

★ 5.0 (29)

From $275.00 USD

Logan Square Walking Tour Experience

An amazing, local's guided tour of one of Chicago's coolest neighborhoods. Learn the history and get advice from a local who knows this area and make your Chica

From $35.00 USD

Luxury Minibus Chicago City Tour with Architecture Cruise Upgrade

Experience the ultimate Windy City adventure on Chicago’s luxury guided minibus tour! Explore 20+ top landmarks with curated photo stops at Cloud Gate "The Bean

★ 4.9 (20)

From $65.00 USD

Luxury SUV 4 Hour Sightseeing Tour

Experience the best of the Chicagoland area in style and comfort with our exclusive SUV tours. Discover the city's iconic landmarks, including the breathtaking

★ 4.0 (1)

From $350.00 USD

Mackinac Island Private Day Tour from Chicago

Discover the charm of Mackinac Island on a delightful journey from Chicago, blending history, culture, and stunning landscapes. Without cars, the island embrace

From $1,350.00 USD

Michigan Avenue Rendezvous GPS App Walking Tour Mobile Game

Venture along Michigan Avenue on an interactive tour to uncover Chicago's hidden gems and iconic landmarks. Dive into the city's rich history, answer trivia, an

From $16.53 USD

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

The Offbeat Street Art Tour is the first tour in Chicago that truly celebrates Chicago's street art scene. No other tour takes guests out into the streets to sh

★ 4.8 (209)

From $40.00 USD

One Day Galena and Dubuque Tour from Chicago

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque, wher

★ 3.0 (2)

From $450.00 USD

Pilsen Chicago Walking Tour: Street Art & Mexican History

Discover Pilsen, one of Chicago’s most vibrant neighborhoods, known for its colorful street art, rich Mexican heritage, historic architecture, and thriving loca

★ 5.0 (8)

From $35.00 USD

Podcast Tour Chicago The Promised Land and the Black Metropolis

Step into the vibrant, resilient heart of Chicago's South Side. On this immersive journey through Bronzeville, you will uncover the epic story of the Great Migr

From $6.87 USD

Podcast Tour Chicago: Culinary Taboos and Rituals

Dive into the unwritten code of Chicago's snack culture. Find out why the locals strictly forbid ketchup on hot dogs, bending forward 45 degrees to eat their It

From $6.87 USD

Podcast Tour Engineering Skyward Chicagos Vertical Pioneers

Trace a century of daring architectural gambles in Chicago's Loop. From six-foot brick walls to soaring glass curtain walls, discover how engineers conquered sw

From $6.87 USD

Prairie Avenue Haunted History Tour and Ghost Hunt

Chicago's original Millionaire's Row, meet the ghosts of the Gilded Age. Marshall Field, George Pullman, Philip Armour, and many more used to live in this amazi

★ 5.0 (12)

From $43.99 USD

Private & All-Inclusive Chicago Downtown Highlights Walking Tour

On this private walking tour our expert local guide will take you to see some of Chicago’s best-known attractions! The day will begin with you meeting with yo

From $223.00 USD

Private 2-Hour Walking Tour: Chicago Loop Interior Architecture

Make the best of your visit to Chicago and explore the interiors of the emblematic Loop of Chicago downtown with a private licensed guide. You will enjoy a priv

From $309.64 USD

Private 45-Minute Chicago Skyline Helicopter Tour

This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience what it is like to fly over the c

★ 4.8 (134)

From $849.00 USD

Private and All-Inclusive Tour of Chicago

Experience the best of Chicago on this private full-day city tour designed for a fun, stress-free day of exploring. Enjoy comfortable hotel pickup, ride in a sp

★ 5.0 (1)

From $750.00 USD

Private Architectural Walking Tour in Chicago Cultural Center

This private architectural walking tour in Chicago reveals a city shaped by cultural ambition and design excellence. You will begin at the historic Cultural Cen

From $869.00 USD

Private Architectural Walking Tour in Chicago Historic Residences

This private architectural walking tour in Chicago explores residences that reflect the city’s design evolution. You will begin along Lake Shore Drive, where ea

From $869.00 USD

Private Architectural Walking Tour in Chicago Loop Landmarks

Skip the crowds this is a private tour for your group only! Embark on a captivating journey through the Loop’s architectural wonders with our Loop Architecture

From $869.00 USD

Private Chicago Architecture Walking Tour

Discover the heart of Chicago’s architectural legacy on this guided walking tour through the historic Loop District. Step back in time as you explore some of th

★ 4.8 (6)

From $211.00 USD

Private Chicago City Minibus Tour

Don’t miss Chicago’s famous sights and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on

★ 5.0 (1)

From $999.00 USD

Private Chicago Food Tour with Deep Dish and Beef Sandwich

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city. You'll experience all the city'

★ 5.0 (88)

From $224.99 USD

Private Chicago Foodie Tour

Taste your way through Chicago on this private half-day walking food tour! Savor local favorites like Portillo’s hot dogs, Al’s Italian Beef, deep dish pizza, G

★ 5.0 (6)

From $288.00 USD

Private Chicago Guided Tour with Hotel Pickup

One of the best ways to explore a city is with a private tour. This tour isn't any different. Have your driver and separate tour guide take you around the most

★ 5.0 (5)

From $805.78 USD

Private Chicago History Museum Tour

Our private walking tour of the Chicago History Museum offers a personalized, in-depth experience led by expert guides who bring Chicago’s vibrant past to life

★ 5.0 (27)

From $162.50 USD

Private Chicago Loop Architecture Walking Tour

Explore the historic Loop District of Chicago on a private walking tour that delves into the city's architectural legacy. With an expert guide, visit iconic sky

★ 5.0 (21)

From $180.00 USD

Private Chicago Street Food Walking Tour With A Local Guide

Immerse yourself in the vibrant food culture of Chicago with a guided walking tour, led by a knowledgeable local guide. Traverse Downtown's diverse culinary lan

From $296.87 USD

Private Christmas Walking Tour in Chicago with Christkindlmarket

This private Christmas walking tour in Chicago captures seasonal traditions within a historic urban setting. You will begin along Michigan Avenue, where archite

★ 5.0 (1)

From $1,029.00 USD

Private City Tour 6-10ppl

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 10 PASSENGERS TOTAL. Thank you for contacting Chicago Private Tours! We would love to help your group discover Chi

★ 5.0 (3)

From $770.00 USD

Private Cultural Walking Tour in Chicago with Lakefront Landmarks

This private cultural walking tour in Chicago presents the city’s architectural heritage and lakefront legacy. You will begin in Millennium Park, where public a

From $869.00 USD

Private Family Walking Tour in Chicago Loop Cultural District

This private family walking tour in Chicago introduces the cultural and architectural identity of the Loop district. You will begin in the financial center, whe

From $669.00 USD

Private Historical Ghost Walking Tour in Chicago Lincoln Park

This private historical ghost walking tour in Chicago explores stories rooted in the city’s layered past. You will walk through Lincoln Park, an area shaped by

From $869.00 USD

Private History and Architecture of Chicago Loop Walking Tour

This is a private walking tour with your group and expert tour guide Dave Lineal. Different tour start times available upon request. I am happy to customize the

★ 5.0 (1)

From $180.00 USD

Private Holiday City Tour

Enjoy the city of Chicago during a magical time! This private experience takes you around Chicago in a private luxury vehicle with your own personal guide! Enjo

★ 5.0 (3)

From $499.00 USD

Private Magnificent Mile Architecture Tour and 360 Chicago Ticket

Experience the story of Chicago through its skyline on a walking tour that stretches from the city’s 19th-century roots to its most striking modern towers. From

★ 4.9 (81)

From $235.00 USD

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed capt

★ 5.0 (73)

From $507.96 USD

Private Shopping Tour from Chicago to Chicago Premium Outlets

Comfortable Roundtrip Tour from your hotel in Chicago to Chicago Premium Outlets - plays host to luxury boutiques and stores selling everything from clothes and

From $284.26 USD

Private Shopping Tour from Chicago to Fashion Outlets of Chicago

Comfortable Roundtrip Tour from your hotel in Chicago to Fashion Outlets of Chicago - plays host to luxury boutiques and stores selling everything from clothes

From $257.90 USD

Private Shopping Tour from Chicago to Lighthouse Place Outlets

Comfortable Roundtrip Tour from your hotel in Chicago to Lighthouse Place Premium Outlets - plays host to luxury boutiques and stores selling everything from cl

From $361.06 USD

Private Tour Art Institute of Chicago Guided Museum

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to the

From $1,031.59 USD

Private Wicker Park and Bucktown Walking Tour

This is your chance to tour the coolest of Chicago's 77 neighborhoods alongside a funny, knowledgeable local guide. You've done the Loop; now it's time to see a

★ 5.0 (3)

From $195.00 USD

Prohibition Chicago: Myth vs. Reality Walking Tour

More than 100 years later, stories of Prohibition-era Chicago still capture the public’s imagination. But the portrayal of that era in popular culture isn't alw

★ 5.0 (4)

From $35.00 USD

Resilience and Revolution: Audio Tour of Chicago’s Black History

Chicago is inseparable from its Black history, where local pioneers helped shape the city’s story. On this self-guided audio tour through downtown Chicago, you’

From $14.99 USD

River North Food Walking Tour

On our 3 hour food walking tour of Chicago, you will taste delectable foods from 5 different delicious places. Tease your tastebuds as you savor foods from Chic

★ 4.6 (98)

From $89.00 USD

Roundtrip Shuttle to South Side and Obama Presidential Center

Discover more of Chicago beyond downtown with this convenient South Side open-top shuttle transfer. Travel from central Chicago to some of the city’s most impor

★ 4.0 (24)

From $10.00 USD

Route 66 Multi Day Tour from Chicago to Los Angeles

Travel the legendary Route 66 in 14 unforgettable days - from Chicago to Los Angeles across eight states, discovering over 450 handpicked points of interest. Ex

From $10.00 USD

Routes POR Route 66 with Audio Guide

Route 66, known as "The Main Street of America", runs through eight states from Chicago to Santa Monica. EN route to Illinois, POR Missouri, Kansas, Oklahoma, T

From $55.02 USD

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lak

★ 4.7 (32)

From $91.23 USD

Secrets of Lincoln Square: Self-Guided Puzzle Quest in Chicago

Roam the lively heart of Lincoln Square with its cafés, delis, and other fun and fascinating stores; stand beside the Berlin Wall; take in ghastly history, gorg

★ 3.3 (3)

From $6.26 USD

Self Guided Ghosts Gangsters and Graves Tour in Chicago

Chicago's prettiest neighborhood hides some of its darkest history. This self-guided audio tour takes you through Lincoln Park on your own schedule, with narrat

From $20.00 USD

Self Guided Podcast Tour Chicago Michael Jordan's West Side

Step into the grit and glory of Michael Jordan’s 1990s Chicago Bulls dynasty. We trace the physical collision between global basketball myth and the reality of

From $5.49 USD

Self-guided podcast tour Chicago: The fight for the waterfront

Discover Chicago's lakefront as a living stage of a decades-long battle for public space. This self-guided podcast tour connects urban planning, architecture, n

From $6.87 USD

Self-Guided Podcast Tour Chicago: The Loops Monumental Canvas

Discover how a city of rigid steel and glass skyscrapers transformed its streets into a world-class, democratic art gallery. On this immersive walking tour thro

From $6.87 USD

Shameless TV Show Location Tour

Experience the ultimate Private Shameless TV Location Tour with the convenience of hotel pick and drop-off, allowing you to sit back, relax and enjoy the ride w

★ 5.0 (5)

From $315.00 USD

Skip the Line Chicago Art Institute Tour Semi-Private 12ppl Max

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour semi-private (1

★ 5.0 (252)

From $90.10 USD

Skip-the-Line Art Institute of Chicago Private Guided Tour

Skip the lines to the iconic Art Institute of Chicago and marvel at world-famous masterpieces by Monet, Van Gogh, and Picasso. Dive into a treasure trove of art

From $318.00 USD

Skip-the-line: Art Institute of Chicago Guided Tour

Beat the crowds with an expert art historian guide on this exclusive early morning tour. Immerse yourself among the masterpieces housed within the acclaimed mus

★ 5.0 (689)

From $71.40 USD

Skyline Lakefront and Millennium Park Chicago Private Day Tour

Explore Chicago’s iconic landmarks and scenic lakefront on a private, fully personalized city tour. Travel in comfort with your English-speaking driver, who sha

★ 5.0 (1)

From $165.05 USD

Small Group Bike Tours From Chicago to Lake Geneva

The route to Lake Geneva follows the incredible coastline of Lake Michigan and eventually into the rolling green hills of Wisconsin. Your group will stop to see

From $449.00 USD

Small Group Tour of Chicago Neighborhoods: North and South Side

This unique tour of Chicago will allow for tourist to see most of Chicago’s 77 neighborhoods and city parks. There is no other tour that tours multiple neighbor

★ 4.5 (55)

From $125.00 USD

Small Group Walking Tour of Chicago The Loop

Explore Chicago with a passionate local guide on a small-group walking tour that takes you beyond the city's most recognizable landmarks. As you stroll through

From $25.00 USD

Taste of Chicago's Chinatown Food Tours

Best Chinatown Food and Walking Tour in town! The Chicago’s Chinatown Food and Walking Tour is a 3-hour immersive culinary and cultural experience designed to h

★ 5.0 (3)

From $85.00 USD

The Art Institute in Chicago Highlights Tour & Photoshoot

Discover the Art Institute in a unique way that blends art, storytelling, and photography. After a warm welcome, we'll head inside with tickets included & begin

★ 5.0 (5)

From $101.00 USD

The Bear Private Pedicab Food Tour of Chicago

If you want culture, history, food, cinema and film and a heavy dose of all things Chicago this is your tour! Get ready to EAT. We are true fans of Chicago, The

★ 5.0 (1)

From $200.00 USD

The Chicago Theatre Tour Experience

A 60-75-minute guided, behind-the-scenes exploration of the historic Chicago Theatre, one of the city’s most iconic landmarks. Stand on the famed Chicago theat

★ 4.0 (59)

From $32.00 USD

The Deep Pockets Of Graceland Cemetery Walking Tour

Dive into this captivating journey through the hallowed grounds of Chicago’s Graceland Cemetery. As we stroll amidst the stunning and serene beauty of historic

★ 4.8 (13)

From $45.00 USD

The Serial Killer and Iconic Chicago Landmarks Bus Tour

Step into the darker side of Chicago’s history on an unforgettable journey where true crime and iconic landmarks intertwine. Discover the Windy City’s infamous

★ 5.0 (4)

From $45.78 USD

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

Embark on a profound, downtown walk-around, to discover incredible stories and secrets of the city on this not to miss feet on the street experience! During our

★ 5.0 (257)

From $44.00 USD

Walking Prohibition Tour

Get a closer look into how alcohol flowed through the streets of Chicago! From the “down and dirty” gangster hangouts, to the “jackets required” establishments

From $45.00 USD

Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck

On your Private Chicago Half Day Highlights tour, visit all the city’s major sites, including favourites such as the Magnificent Mile, Millennium Park and Hanco

★ 5.0 (3)

From $240.00 USD

Welcome to Chicago: The Essential City Tour with photo stops

Learn from a local as you discover Chicago’s top spots for food, drinks, architecture, and culture. On this tour, you'll explore downtown uncovering their histo

★ 5.0 (1)

From $35.00 USD

West Town Hot Spots Tour By Studio W.I.P.

Our tours are not only personable (due to small group sizes), but also create an immersive experience with our knowledge and expertise in street art. What bette

★ 3.6 (5)

From $27.25 USD

Wicker Park Walking Tour History Trivia and Local Flavors

Discover the vibrant Wicker Park neighborhood as you stroll from the Polish Triangle through the Milwaukee Avenue shopping and dining district. This guided walk

★ 3.0 (2)

From $40.00 USD

Wind and Souls an Adults Only Ghost Tour in Chicago

Leave the little ones at home and step into the shadows for a spine-chilling evening designed exclusively for adults. Not all spirits in Chicago are content to

★ 4.3 (48)

From $34.99 USD

️ Chicago Instagram Walking Tour (Private & All- Inclusive)

Our Chicago Walking Instagram Tour will take you to the most Instagrammable spots in Chicago all in one day. If you are looking for a little bit of culture, som

★ 5.0 (2)

From $236.00 USD