Recent Searches
Clear
When are you traveling?
Select Dates
Price
$0
$500+
Duration
Time of Day
RatingClear
Specials

Culture Lover’s Guide to Chicago

Culture Lover’s Guide to Chicago

Chicago boasts a diverse arts-and-entertainment scene that ranges from museums and theaters to comedy clubs and cutting-edge architecture. Here’s how to expand your cultural horizons in the Windy City. 

Head to the Museums

Chicago has a surfeit of world-class museums, making it the ideal stop for culture vultures. Explore the Art Institute, home to works by Seurat and Picasso; head to the Field Museum to scope out dinosaur fossils and learn about natural history; and then continue to the Adler Planetarium for a celestial show. Book your admission tickets in advance to save time on the day. 

Discover Architectural Highlights

From skyscrapers and art deco masterpieces to heritage landmarks such as the Rookery Building and Marina City, Chicago is celebrated for its architecture. Admire top Chicago structures during a narrated river tour by open-top boat; go for a historian-led walking tour to see famous buildings up close; or book a day trip to discover Frank Lloyd Wright’s most significant Chicago-area works.

Spend the Night at the Theater

Chicago rivals New York for its theater scene and range of blockbuster shows. By day, see a different side of the Chicago Theater or the Auditorium Theatre on a behind-the-scenes tour. Then, when the sun goes down, book tickets to a musical at the Lyric Opera.

Go on a Speakeasy Time Warp

Prohibition ranks among the most infamous chapters in Chicago’s history. A variety of history tours bring the 1920s- and ’30s-era to life: take a gangster-themed tour to learn about Al Capone’s notorious crimes or follow a historian to the sites of former underground cocktail bars. 

Hit the Comedy Club Circuit

Many of comedy’s biggest stars—from Tina Fey and Steve Carrell to John Belushi and Stephen Colbert—spent time honing their craft in Chicago. No night out in the Windy City is complete without a tour of its comedy clubs; book tickets to an improv show at The Second City or go on comedy tour to visit several venues in one go. 

Read More
Filter
Select Dates
Today
Tomorrow
Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details

4 Tours and Activities

Sort by: Featured
Chicago Architecture River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Architecture River Cruise

star-5
6769
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).
More
  • 1 hour 15 minutes
  • Free Cancellation
From
$44.69
From
$44.69

Chicago CityPASS

Chicago CityPASS

star-4.5
334
Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Shedd Aquarium, Skydeck Chicago (Opening with reimagined experience in Spring 2021), and the Field Museum plus your choice of admission to 3 of the following attractions: Adler Planetarium, Art Institute of Chicago, Museum of Science and Industry, Chicago, and the 360 CHICAGO Observation Deck. Also enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers.
More
  • 9 days
  • Free Cancellation
From
$109.00
From
$109.00

Behind-the-Scenes Tour of Historic Chicago Theatre

Behind-the-Scenes Tour of Historic Chicago Theatre

star-4.5
21
Tour the historic Chicago Theater, a must-see city landmark, with a guide providing in-depth commentary. You'll get the most out of your visit by traveling with a guide and get access to some areas of the theater that the public never sees. Learn about its architecture, history, and famous performers throughout the years.
More
  • 1 hour
  • Free Cancellation
From
$18.00
From
$18.00

Private Speakeasy Pub Crawl in Chicago with Local Historian
Likely to Sell OutLikely to Sell Out

Private Speakeasy Pub Crawl in Chicago with Local Historian

star-4.5
3
Travel back in time to the 1920s, when Chicago was a prohibition era hub for lively speakeasies. Your guide, a local historian in period dress, will lead you through secret entrances to speakeasies once frequented by bank robbers and Chicago gangsters like Al Capone. Order prohibition era cocktails (additional cost) and listen to stories about bootlegging and racketeering in 1920s Chicago. Guests are welcome to come in period dress.
More
  • 3 hours
  • Free Cancellation
From
$330.00
Price varies by group size
From
$330.00
Price varies by group size