7 Places for a Unique Night Out in Chicago

Chicago
Chicago | © Bert Kaufmann / Flickr

There are almost endless options for a night out in Chicago, with dozens of neighborhoods packed with bars, restaurants, galleries, theaters, concert venues and more. But for those times when a normal night out just won’t do, there are also a number of extravagant, offbeat, and unusual options to discover. Some are uniquely Chicago, and some are just unique.

Windy City Rollers

Roller derby is another thing Chicago created and gave to the world, all the way back in 1935. At Windy City Rollers, you can see home teams such as the Hell’s Belles, Haymarket Rioters, and the All Stars, featuring players with names like Eleanor Bruisevelt, Amelia No Heart, and Yom KaPOW, battle it out for supremacy on the track. Matches take place at the UIC Pavilion in Near West Side or Broadway Armory Park in Edgewater, and tickets are $15.

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Wrigley Rooftops

How often can you watch a game from outside the stadium while enjoying an all-you-can-eat food and drink buffet? Across the street from Wrigley Field, Wrigley Rooftops offers 11 different rooftops on Waveland and Sheffield Avenues for a unique ballgame experience. Enjoy the game with all the comforts of a bar, including 10 different beers on the menu, a constant supply of steak, burgers and hot dogs, and the atmosphere of one of the world’s greatest stadiums.

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Culture Trip Summer Sale

Save up to $1,395 on our unique small-group trips! Limited spots.

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