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Adam Alexander Photography

Do something different in Chicago

Get under the skin of Chicago’s cultural scene by visiting its loveliest neighbourhoods and seeing a new side to America

By Time Out in association with Illinois Tourist Board

Frank Lloyd Wright tour

When a young draftsman arrived in Chicago in 1887, the landscape was still recovering from the Great Fire of 1871. By 1901, Frank Lloyd Wright had designed over 50 of the city’s finest buildings. One of America’s most bold, distinctive and accomplished architects (who went on to design iconic sites like New York’s Guggenheim art gallery), Wright’s buildings still draw crowds for individual tours. There are 13 Frank Lloyd Wright-designed buildings open to the public across Illinois, and in Chicago, you can take the self-guided walking tour around the district most associated with his work – Oak Park. Here you will also find his home and studio.

Wander Roscoe Village

Just like London’s villages reflect the different personalities of the city, so too do Chicago’s. Flowers and trees line the streets around this area between North Center and Lakeview. There’s a cluster of little cafés like John’s Place (the salads, soups and meaty cuts at their White Oak Tavern and Inn are worth checking too) and bars like Village Tap, serving food sourced from local farms and hosting regular live nights.


The 606

Take a walk or hire a bike for a trip along this elevated park, reclaimed from a former train line. The pathway links Logan Square, Humboldt Park, Wicker Park and Bucktown, with plenty of boho beer bars, quirky museums and intriguing community enclaves along its route.

Shopping the districts

For something truly unique, it’s worth exploring Chicago’s different neighbourhoods. Goose Island is the only island on the Chicago River and home to one of the city’s many breweries. The nightlife positively hops here, but you’ll also find one-off gifts and classy crafts. Around Old Town there is, as you'd expect, plenty of character in the setting, even when you're just window shopping. The old German-American heritage is evident as you browse the unusual homeware stories around Lincoln Square, and there are some great boutiques, local shops and dining options around Bucktown and Wicker Park.



You’ll never be bored in Chicago, where entertainment venues are lit up seven nights a week. See a hit Broadway show in the historic downtown theatre district. Laugh at the quick-witted improve of tomorrow’s comedy stars at The Second City or be surprised by the unexpected antics of a trio of bald blue men, and don’t sit in the front row without a rain poncho (trust us!). Listen to some of the best live blues music in the country at The House of Blues. Or steal away to hear sultry cabaret singers in an intimate jazz club with a notorious Prohibition Era past at the Green Mill Jazz Club.

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