Recent Searches
Clear

Top Chicago Cultural Tours

Experience your destination with peace of mind. Learn what steps operators are taking to keep you safe and search for activities with increased health and safety measures. Before you go, check local regulations for the latest information.

Read More
When are you traveling?
Select Dates
Popular
Search experiences that may have limited interaction with crowds.
Search experiences with increased health and safety practices.
Price
$0
$500+
Duration
Time of Day
Rating
Specials

Experience your destination with peace of mind. Learn what steps operators are taking to keep you safe and search for activities with increased health and safety measures. Before you go, check local regulations for the latest information.

Read More
Filter
Select Dates
Today
Tomorrow

53 Chicago Cultural Tours | All Chicago Tours

Sort by:Featured

Loop Interior Architecture Walking Tour with PedwayCity Packages

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.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$29.00
From
$29.00
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.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$45.00
From
$45.00

Gangsters and Ghosts Tour in ChicagoCity Packages

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.
More
  • 2 hours
  • Free Cancellation
From
$27.00
From
$27.00

Best of Chicago: History & Culture Tour with Chocolate and PopcornCity Packages

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.
More
  • 2 hours 30 minutes
  • Free Cancellation
From
$50.63
From
$50.63

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.
More
  • 2 hours to 2 hours 30 minutes
  • Free Cancellation
From
$50.00
From
$50.00

Chicago Pizza TourHalf-day Tours

Chicago Pizza Tour

star-5
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.  Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias.  In just a few hours, you’ll leave stuffed, and with an understanding of why pizza is such an important part of Chicago’s culture.
More
  • 3 hours 30 minutes
  • Free Cancellation
From
$60.00
From
$60.00

Chicago Architecture Walking Tour: Dazzling Interiors of the LoopCity Packages

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.
More
  • 2 hours
  • Free Cancellation
From
$30.00
From
$30.00

Chicago Architecture TourCity Packages

Chicago Architecture Tour

Surround yourself in the Windy City's architectural gems on a 2-hour walking tour. Follow your guide past noteworthy landmarks and lesser known gems. Then visit the Chicago Cultural Center, also known as The People’s Palace, and marvel at the Randolph Street entrance, Grand Army of the Republic Memorial, and more. Beginning at the Clark Street Bridge, the tour concludes next to Millennium Park where you can continue your day of sightseeing.
More
  • 2 hours
  • Free Cancellation
From
$25.00
From
$25.00

Chicago Walking Tour: Modern ArchitectureCity Packages

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.
More
  • 1 hour 45 minutes
  • Free Cancellation
  • Taking safety measures
From
$26.00
From
$26.00
Taking safety measures

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.
More
  • 2 hours
  • Free Cancellation
From
$55.95
From
$55.95

Chicago Private Tour for Two: Lunch, Dessert, Drink IncludedCity Packages

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.
More
  • 3 to 4 hours
  • Free Cancellation
From
$375.00
per group
From
$375.00
per group

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.
More
  • 4 hours
  • Free Cancellation
From
$99.00
From
$99.00

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 .
More
  • 8 days
From
$4,464.00
Price varies by group size
From
$4,464.00
Price varies by group size

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.
More
  • 2 hours 30 minutes
  • Free Cancellation
From
$27.00
From
$27.00

Chicago Walking Tour: A Walk Through TimeCity Packages

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.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$26.00
From
$26.00
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.
More
  • 3 hours 30 minutes
  • Free Cancellation
From
$55.95
From
$55.95

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.
More
  • 3 hours
  • Free Cancellation
From
$660.00
per group
From
$660.00
per group

Train and Walking Tour - Prairie District: Street of the EliteHalf-day Tours

Train and Walking Tour - 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.
More
  • 4 hours
  • Free Cancellation
From
$76.50
From
$76.50

Personal Travel and Vacation Photographer Tour in ChicagoCity Packages

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.
More
  • 1 to 3 hours
  • Free Cancellation
From
$282.29
per group
From
$282.29
per group

Chicago's Pilsen Neighborhood by Train and FootHalf-day Tours

Chicago's Pilsen Neighborhood by Train and Foot

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.
More
  • 3 hours 30 minutes
  • Free Cancellation
From
$65.00
From
$65.00

2 HR History of Chicago Architecture & Art Segway TourCity Packages

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.
More
  • 2 hours
  • Free Cancellation
From
$75.10
From
$75.10

Urban Art 101 in ChicagoCultural Tours

Urban Art 101 in Chicago

Learn about the evolution of urban art in Chicago on this tour that introduces you to works by local and visiting artists. You'll explore the Logan Square neighborhood to see its graffiti and other street art, hearing about the history and future of the art medium along the way.
More
  • 2 hours
  • Free Cancellation
From
$20.00
From
$20.00

Chicago River WalkCultural Tours

Chicago River Walk

Take a tour along Chicago’s newly renovated Riverwalk. Learn about the history of the Chicago River and how it served a pivotal role in the growth of Chicago. See a piece of the World trade centers crumpled steel as well as pieces of the Berlin wall- Germany, The Great Wall of China, The Taj Mahal- India, Cave of the Nativity- Bethlehem, the Great Pyramid- Egypt and the Parthenon- Greece. Go inside the McCormick Bridgehouse & Chicago River Museum and see the river from high above. We end with a stop at one of the riverfront bars/restaurants for your choice of a craft beer or glass of wine (soft drinks for the kids) paired with some light appetizers. Guests are encouraged to hang out, eat and/or take advantage of exclusive drink specials for our groups. 
More
  • 2 hours
  • Free Cancellation
From
$85.00
From
$85.00

Piano Lessons with Susan MerdingerFamily-friendly Shows

Piano Lessons with Susan Merdinger

Take piano lessons instructed by internationally acclaimed Steinway Artist Susan Merdinger, who performed full solo recitals in Carnegie Hall, at her private residence in Highland Park Chicago.
More
  • 1 hour
From
$136.22
From
$136.22

Experiences Themes

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?
Q:
What are the cheapest Cultural Tours in Chicago?

icon_solid_phone
Book online or call
(888) 651-9785
(888) 651-9785