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Top Chicago Cultural Tours

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47 Chicago Cultural Tours | All Chicago Tours

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Loop Interior Architecture Walking Tour with PedwayArchitecture Tours

Loop Interior Architecture Walking Tour with Pedway

star-5
Venture inside renowned Chicago landmarks, elegant lobbies, and underground corridors on this walking tour. Your expert guide will share insights about interior architectural features of this design-rich city—from mosaic domes to the sprawling Chicago Pedway System—bringing the details of the Windy City into vivid focus. Stop to admire Chase Tower, the Marshall Field and Company Building, the Chicago Cultural Center, and more.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$28.00
From
US$28.00
Taking safety measures

Chicago Crime and Mob TourBus Tours

Chicago Crime and Mob Tour

star-4
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
US$45.00
From
US$45.00
Taking safety measures

Gangsters and Ghosts Tour in ChicagoCultural Tours

Gangsters and Ghosts Tour in Chicago

star-4.5
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
US$27.00
From
US$27.00
Taking safety measures

Best of Chicago: History & Culture Tour with Chocolate and PopcornPrivate and Luxury

Best of Chicago: History & Culture Tour with Chocolate and Popcorn

star-5
The Windy City is known for its spectacular architecture and eclectic food scene. Experience both on this tour through the downtown that combines sights with nibbles. Take in famous landmarks like the Wrigley Building, Tribune Tower, and Cloud Gate on foot and with the scenic L train or water taxi along the Chicago River. Taste popcorn and chocolate from two beloved city eateries during the tour.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$50.63
From
US$50.63
Taking safety measures

Chicago Night Crimes TourBus Tours

Chicago Night Crimes Tour

star-4.5
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
US$50.00
From
US$50.00
Taking safety measures

Chicago's Ultimate City Bike TourMountain Bike Tours

Chicago's Ultimate City Bike Tour

star-5
Explore Chicago’s most iconic sites on a bike tour that explores Museum Campus, parks, and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy-going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$45.99
From
US$45.99
Taking safety measures

Chicago Architecture Walking Tour: Dazzling Interiors of the LoopPrivate and Luxury

Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

star-5
See the overlooked highlights of Chicago’s Loop district with a 2-hour walking tour that takes in the best of the bustling, vibrant neighborhood’s inside spaces. Get behind the façades to explore stunningly designed interiors as you follow a specially-designed route with an experienced guide. Learn about the city’s architecture, art and history while visitng a side of Chicago that’s beyond the tourist trail, and experience the Windy City with a local perspective.
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  • 2 hours
  • Free Cancellation
From
US$30.00
From
US$30.00

Chicago Walking Tour: A Walk Through TimeArchitecture Tours

Chicago Walking Tour: A Walk Through Time

star-5
Travel through architectural history on this walking tour that covers Chicago's most famous buildings in chronological order. With a guide in the lead, there's no need to fuss over maps or worry about directions. Simply stroll along and listen to the in-depth guided commentary on Chicago's architectural history; you'll learn about each building and its importance in the architectural canon.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$26.00
From
US$26.00
Taking safety measures

The Chicago Tour-Lunch, Drinks, Dessert, CTA Pass, and City SightsHalf-day Tours

The Chicago Tour-Lunch, Drinks, Dessert, CTA Pass, and City Sights

star-5
Discover some of Chicago’s top attractions—and step off the tourist trail when you visit several of its heritage, locals-frequented neighborhoods—on this introductory, small-group tour. Meet your guide in the Loop, and set off on foot. You’ll spy major landmarks like the Rookery Building, will head to Chinatown for a cultural immersion and delicious dumplings, will glimpse historical architecture in the Prairie District, will explore beautiful Grant Park, and more.
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  • 4 hours
  • Free Cancellation
From
US$99.00
From
US$99.00

Train & Walking Tour: Chicago's Pilsen Neighborhood - Creativity & CommunityHalf-day Tours

Train & Walking Tour: Chicago's Pilsen Neighborhood - Creativity & Community

star-5
Meet your tour guide at Potbelly and enjoy a coffee while you walk through one of Chicago’s earliest skyscrapers. From there, explore a hidden museum inside the Federal Reserve Bank. Next, catch the Pink Line at a renovated L station (opened in 1897) and make your way to Pilsen — a vibrant neighborhood just southwest of the Loop originally settled by Czech immigrants. Upon arrival in Pilsen, you’ll enjoy a taste of authentic Mexican cuisine and visit the National Museum of Mexican Art. While walking through the neighborhood, you’ll experience beautiful street murals and unique homes. After that, you’ll hop back on the train to the Loop and wrap things up with a drink at one of the oldest restaurants in the city.
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  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$65.00
From
US$65.00
Taking safety measures

Chicago Hauntings Original Ghost Bus TourBus Tours

Chicago Hauntings Original Ghost Bus Tour

star-3.5
Calling all fans of the paranormal, this 2.5 to 3-hour ghost bus tour of Chicago takes you into the city’s darkest recesses to reveal its dark past. Travel with ease between locations of reputed haunting and listen to spine-chilling tales delivered by a historian guide. The City Cemetery, the Levee Vice district, and Prairie Avenue all feature on the itinerary, in addition to the site of the notorious St. Valentine’s Day massacre.
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  • 2 hours 30 minutes
  • Free Cancellation
From
US$27.00
From
US$27.00

Historic Chicago South Side Tour and 360 CHICAGO Observation DeckBus Tours

Historic Chicago South Side Tour and 360 CHICAGO Observation Deck

star-5
Discover the historical sights of South Chicago on a 2-hour group walking tour. Select the morning or afternoon start time, depending on your preference. Follow your guide to Grant Park, Buckingham Fountain, Obama's House, and other sites that define the historical South Side. Pause for photos and ask questions at any time. You also get a free ticket to the 360 Chicago Observation Deck, which you can use at anytime until 10:30pm.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
US$55.95
From
US$55.95
Taking safety measures

Scenic Chicago North Side Tour and 360 CHICAGO Observation DeckHalf-day Tours

Scenic Chicago North Side Tour and 360 CHICAGO Observation Deck

Discover the sights of North Chicago on a 2-hour group walking tour. Offered in the morning and afternoon, select a start time that fits with your schedule. Follow your guide to Millennium Park, Lake Michigan, and more. Feel free to pause for photos and ask questions whenever you like. You also get free admission to the 360 Chicago Observation Deck, which you can use at anytime until 10:30pm.
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  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$55.95
From
US$55.95
Taking safety measures

Great Lakes Explorer Classic AmericanaMulti-day Tours

Great Lakes Explorer Classic Americana

This 8-day small group journey from Chicago takes you around and across Lake Michigan. From the architecture and music of Chicago to going back in time on Mackinac Island, the Great Lakes region truly is a magical experience. American Experiences small group, multi-day tours provide you with authentic, in-depth experiences not found elsewhere. Your trip includes more than just the basics-- a welcome reception, one or two unique specialty meals, three and four star quality boutique hotels, multiple guided tours with opportunities to choose your activity as well as free independent exploration, and transportation. Plus, our knowledgeable tour guide stays with you for the duration of the trip and can personalize your experiences to meet the needs of both you and the group. Get to know like-minded people from all over the world who enjoy similar experiences and enrich your appreciation of America's magical Great Lakes with American Experiences small group tours .
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  • 8 days
From
US$4,464.00
Price varies by group size
From
US$4,464.00
Price varies by group size

Chicago Private Tour for Two: Lunch, Dessert, Drink IncludedPrivate and Luxury

Chicago Private Tour for Two: Lunch, Dessert, Drink Included

This tour is a private tour for two people and is an overview of what makes Chicago so fascinating-the neighborhoods, history, architecture, culture, and foods. We will take you beyond the downtown loop to explore some of the great neighborhoods that make up this amazing and diverse city. The Chicago Tour will help you see the city without worrying about the logistics or the effort of planning. We will explore the Loop, Chinatown, South Loop/Prairie District, and end in Grant Park. Be prepared to walk a lot as we will explore by foot and use the public transit. Together we will see the city by going off the beaten path for a more authentic experience. Each tour will include all food and drinks (listed in the itinerary below) and an unlimited public transit day pass. You may add extra people for an additional $50pp. This must be arranged by emailing us. Also, we can adjust the itinerary based upon interests. All private tours will include lunch, dessert, and drink.
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  • 3 to 4 hours
  • Free Cancellation
From
US$375.00
per group
From
US$375.00
per group

Chicago Walking Tour: Modern ArchitectureArchitecture Tours

Chicago Walking Tour: Modern Architecture

star-4.5
Embark on a walking tour of Chicago's more-recent architecture heritage with a 2-hour stroll highlighting the city's modern, postmodern, and international structures. Especially known for its architectural originality, Chi-town boasts everything from the elegant metal and glass tower of One South Dearborn to the Harold Washington Library, with its Beaux-Arts inspired exterior. Your guide will highlight these and other unique buildings, relaying background on their individual histories and construction en route.
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  • 1 hour 45 minutes
  • Free Cancellation
  • Taking safety measures
From
US$26.00
From
US$26.00
Taking safety measures

Train & Walking Tour: Chicago's Prairie District - Street of the EliteHalf-day Tours

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

star-5
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
US$76.50
From
US$76.50
Taking safety measures

Your Way or the Highway: Customized Private Walking Tour (EN - FR - NL)Half-day Tours

Your Way or the Highway: Customized Private Walking Tour (EN - FR - NL)

star-5
Enjoy a private 4-hour walking tour with Belgian-American tour guide Leentje. She will introduce you to the city she calls home since 2014. Every tour is different and custom-made. Tours are available in English, French or Dutch. Focus can be on public or street art, architecture, food and much more!
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
US$320.00
per group
From
US$320.00
per group
Taking safety measures

Train & Walking Tour: Wicker Park - Putting the Chic in ChicagoHalf-day Tours

Train & Walking Tour: Wicker Park - Putting the Chic in Chicago

Are you ready to see Chicago’s trendiest, upscale neighborhood? Join us on a trip to Wicker Park! We’ll meet for coffee in a popular shop located in one of Chicago’s neo-Gothic landmark buildings. Making our way to the train, we’ll also visit what was once the largest office building in the world. We’ll then board the Blue Line and head to Wicker Park. Once there, we’ll enjoy a small bite and then stroll this trendy neighborhood. We’ll see original and newly-restored buildings, famous mansions, a beautiful park, the business district, and grab another quick bite before we jump on the Blue Line again and head back to the Loop. We’ll end our tour with another national landmark building and a sweet treat at a popular food hall.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$65.00
From
US$65.00
Taking safety measures

Private Al Capone Gangster Tour in ChicagoHalf-day Tours

Private Al Capone Gangster Tour in Chicago

star-5
Chicago’s mob history has long been immortalized in popular media. Embark on this Chicago Gangster Tour to learn the true story. With an expert historian as your guide, you’ll visit notorious hangouts of John Dillinger, The Untouchables, and the legendary Al Capone. You’ll stop at former speakeasies, historic hotels, and epic crime sites like that of the Saint Valentine’s Day Massacre.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$660.00
per group
From
US$660.00
per group
Taking safety measures

2 HR History of Chicago Architecture & Art Segway TourPrivate and Luxury

2 HR History of Chicago Architecture & Art Segway Tour

star-5
Explore the art and architectural highlights of Chicago on a Segway during this guided tour. This family-friendly tour takes visitors by the outdoor sculptures, landmark buildings, and iconic skyline of the city. Accompanied by educational and informative commentary, this city tour saves you from hours of walking and lets you see all of Chicago's top art and architectural attractions in one tour.
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  • 2 hours
  • Free Cancellation
From
US$75.10
From
US$75.10

Chicago Insider Segway TourPrivate and Luxury

SPECIAL OFFER

Chicago Insider Segway Tour

star-5
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 Chicago. We will travel back through the ages as you discover the city through the lens of the Chicago Syndicate, hear the whispers of the city’s elite (or politicians), and be entertained by stories that are rarely told. You’ll think “No, really I never would have known!” Glide around Millennium Park, through the new neighborhood of Lakeshore East, and along the Lakefront as we unveil Chicago’s forgotten past in two hours! Your imagination will come alive as you hear stories of the Chicago Mob, the truth behind the 1968 Democratic National Convention, innovations that changed history, and so much more!
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  • 2 hours
  • Free Cancellation
From
US$64.99
US$75.58
US$10.59 savings
From
US$64.99
US$75.58
US$10.59 savings

Magic Christmas Tour in Illinois (Chicago)Private Sightseeing Tours

Magic Christmas Tour in Illinois (Chicago)

The exclusive tour only in the Christmas period! This special times brings magic Chicago, Illinois. Chicago is known for being a architectural city from the slopes of the John Hancock center to the Boxy sides of the Willis tower. Together with the professional local guide, you will visit the most beautifully decorated places. You will feel spellbound with the charming atmosphere in the streets which you can feel only this time of the year! What is the story of the Christmas tree? Who was the first to decorate it in the world? What magical things can happen during the Christm as period? Have you heard about Christmas spells? You will hear miraculous Christmas legends about Chicago, Illinois. You will visit the old-fashioned Christmas Market in the city. What makes it so popular? What local products is must taste at Christmas? Fill your heart with the joy and experience magic Chicago, Illinois.
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  • 2 hours
From
US$769.01
per group
From
US$769.01
per group

Personal Travel and Vacation Photographer Tour in ChicagoPrivate and Luxury

Personal Travel and Vacation Photographer Tour in Chicago

Document your travels with professional, candid, photos from your trip to Chicago. Choose from a one or two-hour session in a variety of locations, Whether it’s a romantic getaway, a family vacation, or special occasion, capture the moments with a professional travel photographer by your side. Put the selfie stick away and work with your knowledgeable local photographer to find the perfect locations for your photos. You will be ale to access your digital gallery within five working days of the tour.
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  • 1 to 3 hours
  • Free Cancellation
From
US$297.52
per group
From
US$297.52
per group

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