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The best things to do on a first date in Chicago

Sneak into Chicago's most secretive bars, hit up free museum days and check out live comedy for a great first date in Chicago

Photograph: John Khuu
Billy Sunday

There's no getting around it: First dates are awkward. It's tough to tell what activities are too boring, too much or too intimate. Just because there's so much to do in Chicago, doesn't mean it's all the right thing to do for a first date. We sifted through all the best restaurantsbarsmovie theaters and more to help you plan the perfect first encounter. You just need to come up with some charming anecdotes and make your bed. 

Recommended: Our complete guide to dating in Chicago

The best things to do on a first date in Chicago

Sneak into Chicago's most secret bars

Impress your date from the start by taking him or her out to one of Chicago's hidden speakeasies. From secret cocktail lounges to a subterranean Japanese izakaya, we've got the insider scoop on how to access top-secret bars all over Chicago. Even if you don't hit it off, at least you'll have an adventure getting into these swanky spots.

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By: Time Out Chicago editors

Hit up a free museum day at the best Chicago museums

A free museum visit is the perfect, low-stakes activity: If your date isn't into it (or they're really into you), you can bail whenever you please, guilt-free. But you probably won't want to leave the best Chicago institutions. If you're willing to plan ahead, you can take in masterpieces at the Art Institute or gaze at tropical fish while strolling through Shedd Aquarium—all without spending a dime. 

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By: Zach Long

Get tipsy at a beer festival

Beer fests are as common in Chicago as sales tax and corrupt politicians. Spend an afternoon day-drinking with your date at a neighborhood beer fest. No matter where you go, you can sample an impressive range of delicious craft beers, both local and national. Take a look at our list of the best Chicago beer festivals and start planning your next weekend of tastings. If you want to thank us, you can buy us a beer.


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By: Zach Long

Go gallery hopping in Pilsen

On the second Friday of each month, The Chicago Arts District hosts 2nd Fridays Gallery Night, a series of receptions at the galleries and artists' studios centered around South Halsted Street. Pick up a map at the information center at 1945 S Halsted St and visit the creative spaces free of charge as they open their doors to showcase an exciting display of art from Chicago and beyond.

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Chicago Arts District , Lower West Side Friday September 8 2017 - Friday December 8 2017

See a free movie screening in the park

Seeing a movie on a first date sounds like a good idea, until you realize you're just sitting silently next to a cute stranger for two hours. Ditch megaplex prices and awkward movie theater silence for Chicago Park District's annual Movies in the Parks series, which offers free entertainment from Rogers Park to Hegewisch. Just don't forget to BYOR (Bring Your Own Raisinets).



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By: Kris Vire

Dance it up at Kingston Mines

You don't have to dance at Kingston Mines—there's plenty of seating—but you'll have a hard time keeping your feet still at this Lincoln Park blues club. The space has an unusual setup: two different bands in two different rooms on two different stages. Pay the cover (usually $12–$15) and you'll be treated to multiple sets from local acts and, if you're lucky, a few touring bands. 

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Sheffield & DePaul

Get your mini golf on

Mini golf is ripe with light competition and ample opportunity for flirty banter. The mini golf course at the Diversey Driving Range, situated right in Lincoln Park near Belmont Harbor, is an idyllic first date spot. The course is suited for golfers of all ages and skill levels, and while there's no animatronic obstacles, there are plenty of bridges and waterfalls. 

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Lake View

Take a stroll through the Lincoln Park Zoo

Sure, it's a little cliché, but taking a walk through the Lincoln Park Zoo is a great way to get to know someone. Visit the 1,200 animals, from apes to zebras, at one of the few free zoos left in the country. Cap off your trip to the Lion House with a coffee at Café Brauer or drinks at the J. Parker.

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Lincoln Park

Catch a show at the Hideout

Drop in on whatever's happening at the Hideout—on any given night, it could be stand-up comedy, live music or a DJ set. If the show isn't your cup of tea, you can always retreat to the bar (which is separate from the performance space) or take your drinks outside. Best of both worlds. It can be difficult to reach this juke joint via public trans, but it is worth it for the cheap beer, live country-rock and DJs dropping nostalgia, from Prince to Devo.  

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River West/West Town

Explore the Garfield Park Conservatory

What's more romantic than a walk through the woods? Well, since we're city-dwellers and that's not an option, Garfield Park Conservatory is the next best thing. Described as “landscape art under glass” when it opened in 1908, the conservatory boasts revolutionary architecture. About 120,000 plants representing some 600 species occupy the conservatory’s 1.6 acres—perfect for getting lost with a new friend.

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East Garfield Park
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