7 Places for a Unique Night Out in 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.

1. The Improvised Shakespeare Co.


What’s more unique than improv? As the home of improv comedy, Chicago has a fair few places to see some. However, for something a bit different, why not combine it with history’s greatest playwright? From one audience suggestion, this talented troupe will improvise a two-act play utilizing the style, language, and themes of William Shakespeare. You can catch The Improvised Shakespeare Co. at the iO Del Close Theater on Thursday at 8 pm, and Friday and Saturday at 8 pm and 10:30 pm.

The Improvised Shakespeare Co., 1501 N Kingsbury St, Chicago, IL, USA, +1 312 929 2401


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.


2. Chocolate at the Pen


If eating out is all about the dessert for you, why not just skip the rest? Held in the lobby of The Peninsula, a chic hotel just off the Magnificent Mile, Chocolate at the Pen is a buffet offering a variety of chocolate delicacies and one- and two-bite desserts. While it’s a bit pricey at $40, it’s a rare opportunity to indulge in many delicious desserts. A must for any chocolate lover, it takes place every Friday and Saturday from 7 to 10:30 pm, and a reservation is recommended.

Chocolate at the Pen, The Peninsula, 108 E Superior St, Chicago, IL, USA, +1 312 337 2888


3. The Old Town Ale House


Old Town Ale House | © victorgrigas/WikiCommons
© victorgrigas/WikiCommons

Staying on the north side but moving from the elegant to the unusual, the Old Town Ale House is undeniably unique; owned by painter Bruce Elliott, his work covers the walls. The most infamous pieces are the political portraits, including a nude Sarah Palin holding an assault rifle and jailed former governor of Illinois Rod Blagojevich being strip-searched. It was called “The best bar in the world that I know about” by legendary film critic Roger Ebert.

Old Town Ale House, 219 W North Ave, Chicago, IL, USA, +1 312 944 7020

Old Town Ale House | © victorgrigas / WikiCommons

4. Leather Archives & Museum

Library, Museum, Park

Almost 10 miles (16 kilometers) north of the Loop in Rogers Park, the Leather Archives & Museum has dedicated itself to the preservation of leather, kink and fetish lifestyles since 1991. With a library, museum and archives, there is erotic art, historical sadomasochism devices, papers and records from notable activists, artists, organizations and much more to see. Not quite a night out as it closes at 7 pm on Thursday and Friday, but certainly unique.

Leather Archives & Museum, 6418 N Greenview Ave, Chicago, IL, USA, +1 773 761 9200

Leather Archives and Museum | © Amy G / Flickr

5. Helltrap Nightmare

A series of nights devoted to comedy horror and noise music terror, featuring a rotating lineup of the wildest and most radical local stand-ups and experimental musicians, Helltrap Nightmare is the brainchild of Chicago-based comedian Sarah Sherman. Since debuting in early 2016, the show has gone from strength to strength, grossing and freaking out audiences on a monthly basis at The Hideout in West Town. Sherman was named “Best stand-up comic” in the Chicago Reader’s 2016 readers’ poll.

Helltrap Nightmare, The Hideout, 1354 W Wabansia Ave, Chicago, IL, USA, +1 773 227 4433


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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