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Culture Lover’s Guide to Chicago

Check out the city's best museums and theaters with this guide.

Tourists check out the Bean in the rain in Chicago
Hi, I'm Claire!

Claire Bullen is an award-winning food, drinks, and travel writer and editor who has lived and worked in Chicago, Philadelphia, New York, Paris, and London. She is the author of The Beer Lover's Table: Seasonal Recipes and Modern Beer Pairings, and the editor at GoodBeerHunting.com. Her writing has also appeared in Time Out New York, The Daily Meal, Pellicle Magazine, and beyond.

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

The Field Museum in Chicago.
The Field Museum.Foto: Sam Girton / Viator

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. 

Spend the night at the theater

The theater scene in Chicago is world-class.
The theater scene in Chicago is world-class.Foto: elesi / Shutterstock

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

A night at Tommy Gun's is always a joy.
A night at Tommy Gun's is always a joy.Foto: Sam Girton / Viator

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

People walk past Second City, a comedy club, in Chicago.
The Second City is where many stars began their career.Foto: Second City / Tripadvisor

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 a comedy tour to visit several venues in one go. 

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