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29 results | All Chicago Tours

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Chicago Architecture River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Architecture River Cruise

star-5
6480
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
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  • 1 hour 15 minutes
  • Free Cancellation
  • Taking safety measures
From
USD44.69
From
USD44.69
Taking safety measures

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1046
Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
USD45.00
From
USD45.00
Taking safety measures

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
1938
Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
USD27.00
From
USD27.00
Taking safety measures

Chicago Architectural River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Architectural River Cruise

star-4.5
704
See the towers, piers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
USD49.05
From
USD49.05
Taking safety measures

Chicago Lake and River Architecture Tour

Chicago Lake and River Architecture Tour

star-4.5
504
Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
USD40.00
From
USD40.00
Taking safety measures

Chicago in a Day: Food, History and Architecture Combo Tour
Likely to Sell OutLikely to Sell Out

Chicago in a Day: Food, History and Architecture Combo Tour

star-5
126
An excellent choice for first-time visitors, this tour provides a comprehensive overview of the city and hits on both classic attractions and little-known sites. Beginning at the Chicago Theatre, work your way to the Chicago Pedway, an elaborate network of underground tunnels used by locals and commuters. Stroll the Chicago Riverwalk and the Magnificent Mile, then embark on a food tour to taste some of the city’s famous foods.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
USD104.00
From
USD104.00
Taking safety measures

Chicago Night Crimes Bus Tour
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Chicago Night Crimes Bus Tour

star-4.5
99
Discover the ‘dark side’ of the Windy City thanks to this 2.5-hour, bus-based, nighttime crime history tour of Chicago. Explore the lives of notorious mobsters like Al Capone, Frank Nitti, Bugs Moran, and more as you explore infamous crime scenes like the St. Valentine’s Day Massacre, learn about ‘The Enforcer’s Safe,’ and stop by local watering holes.
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  • 2 hours to 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
USD50.00
From
USD50.00
Taking safety measures

Chicago City Minibus Tour with Optional Architecture River Cruise

Chicago City Minibus Tour with Optional Architecture River Cruise

star-5
429
Explore Chicago's iconic landmarks on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore downtown and Northside neighborhoods. You have a chance to get out and visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.
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  • 2 to 4 hours
  • Free Cancellation
  • Taking safety measures
From
USD39.95
From
USD39.95
Taking safety measures

Chicago Walking Tour: Art Deco Skyscrapers
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Chicago Walking Tour: Art Deco Skyscrapers

star-4.5
78
Admire the incredible façades and intricate interiors of the Windy City's 1920s art deco and art moderne buildings during this architecture walking tour of Chicago. Uncover the history of Chicago art deco architectural along with the city's influential role in the development of this iconic artistic style, as you get an up close and personal look at its wealth of gorgeous period buildings. This art deco Chicago walking tour also includes a certified guide.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
USD30.00
From
USD30.00
Taking safety measures

Field Museum of Natural History Admission Tickets
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Field Museum of Natural History Admission Tickets

star-4.5
147
Delve deep into the world of natural history with this Field Museum admission ticket in Chicago. Spend as long as you like exploring the museum's collection of more than 26 million artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Time travel through 13,000 years of history in the Americas, from the Ice Age to Inca and Aztec temples. Take advantage of the free daily tours, led by Field Museum docents.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
USD26.00
From
USD26.00
Taking safety measures

Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

star-5
503
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 Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.
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  • 1 hour 30 minutes
  • Taking safety measures
From
USD56.00
From
USD56.00
Taking safety measures

90-Minute Chicago River Architecture Tour

90-Minute Chicago River Architecture Tour

star-4.5
1150
Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
USD40.00
From
USD40.00
Taking safety measures

Chicago Private Tours

Chicago Private Tours

star-5
143
Have only a short stay planned in Chicago? Make the most of your time in the Windy City, and see more of the city in less time, when you book a private driving tour of Chicago. Pick between several convenient tour times, and meet your guide and driver directly at your hotel. Over the course of your excursion, you’ll make stops at highlight attractions like the Lincoln Park Conservatory, Millennium Park, and Museum Campus. You’ll also learn about Chicago’s history and can spy other remarkable sights as you go.
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  • 3 to 4 hours
  • Free Cancellation
  • Taking safety measures
From
USD425.34
per group
From
USD425.34
per group
Taking safety measures

Chicago Walking Tour: Historic Treasures of Chicago

Chicago Walking Tour: Historic Treasures of Chicago

star-5
22
Get an insider's introduction to Chicago's most celebrated buildings during this architecture-focused walking tour of Michigan Avenue and State Street. Revisit the heyday of the skyscraper and visit stunning, Art Deco-era interiors, from the Palmer House Hotel to the Chicago Cultural Center. Admission to the Chicago Architecture Center is included, with an introduction by the docent.
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  • 1 hour 45 minutes
  • Free Cancellation
  • Taking safety measures
From
USD30.00
From
USD30.00
Taking safety measures

Train & Walking Tour: Chicago's Prairie District - Street of the Elite

Train & Walking Tour: Chicago's Prairie District - Street of the Elite

star-5
9
Step off the typical tourist trail, and discover one of Chicago’s oldest and most scenic neighborhoods, on this walking tour of the Prairie District. Meet your guide in the morning at the Chicago Athletic Association, and set off with just a small group for company. The Prairie District is just a short L ride away; you can look forward to seeing the Second Presbyterian Church, Glessner House, Motor Row, and otherwise discovering how Chicagoans lived at the turn of the 20th century.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
USD90.00
From
USD90.00
Taking safety measures

Chicago Insider Segway Tour

Chicago Insider Segway Tour

star-5
42
Enjoy an introduction to Chicago’s highlights and history—on wheels. This small-group Segway tour offers a new, and zippy, way to explore. Meet your guide near Millennium Park, and begin with a personalized training session. Once you’re comfortable on your Segway, explore Millennium Park, roll along the Lakefront, and more. As you go, learn little-known Chicago stories and tidbits, from mafia history to the innovations that changed the city.
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  • 2 hours
  • Free Cancellation
From
USD75.58
From
USD75.58

Art Institute of Chicago Skip-the-Line Small-Group Guided Tour

Art Institute of Chicago Skip-the-Line Small-Group Guided Tour

star-5
22
Explore one of the country’s great art museums—and discover many of its collection highlights—on this small-group Art Institute of Chicago tour. Meet your guide right out front, and see works from artists the likes of Picasso, Chagall, Seurat, O’Keeffe, and many more. As you go, your guide will share the stories behind the masterpieces, and will help bring the history of the museum and its collection to life.
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  • 2 hours to 2 hours 30 minutes
  • Free Cancellation
From
USD100.70
Price varies by group size
From
USD100.70
Price varies by group size

Workers Cottages of Oldtown Triangle Walking Tour

Workers Cottages of Oldtown Triangle Walking Tour

star-5
13
This tour will show you many of these delightful cottages and the different styles they were designed and constructed in. You will also learn about their history and unique part of the growth of the city of Chicago. Plus you will hear about other fascinating Chicago history that dates back 150 years and beyond! The Oldtown Triangle is one of the oldest and most quaint areas of the city - an area that many Chicagoans love and cherish. You will feel like you have left the hustle and bustle of the city and will instantly be transported to another place, another time, specifically the late 1800's!
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  • 1 hour 45 minutes
  • Free Cancellation
  • Taking safety measures
From
USD35.00
From
USD35.00
Taking safety measures

Ugly Buildings Tour

Ugly Buildings Tour

star-5
16
Chicago is the architectural capital of the country and has so many tours profiling these wonderful, beautiful buildings. Hiding around these architectural masterpieces, however, are UGLY BUILDINGS. This “educational roast” teases these buildings and creates a conversation on what makes a building pretty or ugly. These opinions are all subjective, and participants are encouraged to share their perspectives whether or not they agree. IMPORTANT NOTE: There are jokes about Trump Tower along with the person it is named after on this tour. There is also one swear word used, because it is an important part of a story. If you don’t think you would find these kinds of jokes funny, I recommend choosing any other architectural tour. There are so many stories and perspectives on Ugly Buildings I have not previously been able to share on any other tours. I am really excited to have you along for this experience that is unlike any other tour in Chicago!
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
USD30.00
From
USD30.00
Taking safety measures

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

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

star-5
12
The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2 to 2.5 hour private guided museum tour, you’ll be able to skip the line and explore it’s most famous pieces with the help of an engaging guide who will lead the way. Highlights Generally Include: (if artwork is not on loan or being restored etc.) Paris Street, Rainy Day by Gustave Caillebotte Sunday on La Grande Jatte - Georges Seurat Sky Above Clouds - Georgia O'Keefe Nighthawks - Edward Hopper A Picture of Dorian Gray - Ivan Albright America Windows - Marc Chagall The Old Guitarist - Pablo Picasso Inventions of Monsters - Salvador Dali Four Mona Lisas - Andy Warhol
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  • 2 hours to 2 hours 30 minutes
  • Free Cancellation
From
USD153.70
Price varies by group size
From
USD153.70
Price varies by group size

Underground Donut Tour - West Loop & Restaurant Row
Likely to Sell OutLikely to Sell Out

Underground Donut Tour - West Loop & Restaurant Row

star-5
8
The West Loop (or Restaurant Row) Donut Tour is a sister tour to our Original Downtown Tour. Geared towards those who want to see Chicago’s authentic foodie focused food scene, this is the tour for you! We’ll start on the west side of the loop and wander our way along Randolph and various side streets, showing off some of the more unique spots in the West Loop. Bring your appetite, as you’ll be sampling donuts from 4 of the top donut shops in the West Loop. Some of which you probably had no idea they even served donuts. Along the way, you’ll learn about the history of Randolph street and the many warehouses that line it as well as some other Chicago history you might not find elsewhere.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
USD30.00
From
USD30.00
Taking safety measures

Saturday Chicago Pizza History and Tastings Bus Tour

Saturday Chicago Pizza History and Tastings Bus Tour

star-5
6
Foodies will enjoy this tour of Chicago that focuses on one of the city’s most popular dishes: pizza. Although your guide can’t tell you once and for all whether Chicago or New York has the best pizza in the USA, they will teach you about Chicago’s ten different types of pizza, let you sample four, and give you exclusive access to pizza kitchens. A fun tour for all pizza lovers.
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  • 3 hours 30 minutes
  • Taking safety measures
From
USD90.00
From
USD90.00
Taking safety measures

Full-Day Small-Group Tour of Chicago Neighborhoods with Lunch and Dinner

Full-Day Small-Group Tour of Chicago Neighborhoods with Lunch and Dinner

star-5
5
Explore Chicago like a local—and visit the city’s distinctive, characterful neighborhoods, in addition to its major landmarks—on this full-day tour. Set off from downtown with just a small group for company, and leave the driving to your guide—you’ll explore dozens of Windy City neighborhoods, from Hyde Park and Bronzeville to Lincoln Park and the Gold Coast. Learn all about Chicago culture and history as you go.
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  • 8 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
USD175.00
From
USD175.00
Taking safety measures

Chicago Walking Tour: The Magnificent Mile

Chicago Walking Tour: The Magnificent Mile

star-5
1
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 district. Hear the secrets and stories behind the striking buildings on North Michigan Avenue that have become architectural icons. Developed over the past 100 years, the street includes historically-inspired architecture in Parisian, Gothic, neoclassical and Art Deco styles sprinkled among Modern and 21st Century buildings. You’ll see skyscrapers, vertical malls, hotels, residential towers and some buildings that were designed to embody the brands sold inside.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
USD30.00
From
USD30.00

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What people are saying about Cultural Tours in Chicago

star-5
Chicago Architecture River Cruise
"The architecture and historical references provided a great experience. The cost was worth the value."..."
star-5
Chicago Crime and Mob Bus Tour
"Our guide Leah was excellent! Would definitely recommend this tour. It gave city history along with crime history."..."
star-5
Gangsters and Ghosts Tour in Chicago
"Excellent tour on a beautiful day! The guide was very informative. Will definitely recommend this tour."..."
star-5
Chicago Architectural River Cruise
"Knowledgeable & professional staff. The buildings were unbelievable and the history lesson was great."..."
star-5
Chicago Lake and River Architecture Tour
"This was one of the best way to see one of the most beautiful cities in the world, the boat tour it's a must 🙏👍"..."
star-5
Chicago in a Day: Food, History and Architecture Combo Tour
"Kelly, our guide was extraordinary. She was knowledgeable, patient and fun. The length of the tour was just right, and provided the perfect 1st day orientation of this amazing city"..."
star-5
Chicago Night Crimes Bus Tour
"Katie was very informative and entertaining. Enjoyed seeing the neighborhoods we went through and many restaurants."..."
star-5
Chicago City Minibus Tour with Optional Architecture River Cruise
"Very nice experience and tour guide was very nice. My husband and I were very impressed with the stops and views. Thank you!"..."
star-5
Chicago Walking Tour: Art Deco Skyscrapers
"David took us to a trip to the past. Art Deco can be hidden or glowing in front of you and David gave us tips on how to recognize it. He took us to amazing places around Downtown where this style exists. Thank you for sharing with us! We highly recommend this tour!"..."
star-5
Field Museum of Natural History Admission Tickets
"What a wonderful, educational experience! We thoroughly enjoyed touring the museum and leisurely exploring different exhibits. The mammals exhibit and Nature Walk were especially well designed and the animals looked as through they could be living and breathing in their glass enclosures. It was absolutely fantastic!"..."
star-5
Chicago Architecture Center River Cruise aboard Chicago's First Lady
"Excellent start to finish including the boat captain, and especially the knowledgeable docent Dan J."..."
star-5
90-Minute Chicago River Architecture Tour
"Wonderful tour, highly recommend! Great tour guide! A must do in Chicago. Great company and easy access."..."
star-5
Chicago Private Tours
"We loved how knowledgeable our tour guide was. He had so much information about the city. We really enjoyed driving around the city."..."
star-5
Chicago Walking Tour: Historic Treasures of Chicago
"Amanda did an excellent job giving the highlights of the city! She answered all our questions and gave recommendations of things to do on our own."..."
star-5
Train & Walking Tour: Chicago's Prairie District - Street of the Elite
"We like to know the history of cities we visit, and this tour gave us a glimpse of Chicago of the 1800s visiting homes, grand hotels and also simply strolling around places with a story. The tour guide was excellent."..."
star-5
Chicago Insider Segway Tour
"Clark was a great tour guide! Our first time on Segways and he was a great teacher. He was funny and knowledgeable"..."
star-5
Art Institute of Chicago Skip-the-Line Small-Group Guided Tour
"Marlin made sure we had a wonderful experience. He was super attentive and worked hard to weave stories into his tour which made a more memorable experience. It was a very enjoyable day!"..."
star-5
Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket
"Mandy is an awesome guide, with a ton of knowledge and insight into the art, the history of the museum, and Chicago in general. A really great tour!"..."
star-5
Saturday Chicago Pizza History and Tastings Bus Tour
"Steve was very informative and a fun tour guide. Getting to meet the business owners and hear their stories and passion for pizza was an extra special treat. Learning interesting facts about Chicago on the bus ride was great as well. All four pizzas were delicious and different styles. Highly recommend this tour!"..."
star-5
Full-Day Small-Group Tour of Chicago Neighborhoods with Lunch and Dinner
"Our tour guide, Steve, was AMAZING!! Very knowledgeable and friendly! Steve was very accommodating and made us feel so comfortable, it was like visiting a friend I’ve always known! If you’re ever in Chicago and want to take a tour of the City, I definitely recommend Steve as your tour guide."..."

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best Cultural Tours in Chicago?
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What Cultural Tours in Chicago are taking additional safety precautions?
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What Cultural Tours in Chicago are good for avoiding crowds?