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.