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Photograph: John Khuu

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

By Grace Perry

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

Red Rum
Photograph: Andrew Nawrocki

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.

Art Institute of Chicago interior
Courtesy of the Art Institute of Chicago

Hit up a free museum day at the best Chicago museums

Things to do

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. 


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.


See a free movie screening in the park

Things to do

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).



Photograph: Max Herman

Dance it up at Kingston Mines

Music Folk, country and blues Sheffield & DePaul

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. 

mini golf ball
Photograph: Pixabay

Get your mini golf on

Sports and fitness Golf Lake View

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. 


Take a stroll through the Lincoln Park Zoo

Things to do Lincoln Park

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.

Photo: Julia Korol

Catch a show at the Hideout

Bars Dive bars River West/West Town

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.  


Explore the Garfield Park Conservatory

Attractions Parks and gardens East Garfield Park

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.

Photograph: Martha Williams

Get drinks at a charming local dive


Talk about a stress-free date activity. Fancy nights out are fun and all, but sometimes you just want to grab a barstool at a place that doesn't require a dress code. We love these dives because the bartenders won't judge you for ordering the cheapest beer on the menu. Visit one of these no-frills beer bars and neighborhood taverns, but don't forget to stop by the ATM before ordering your drink—many of these bars are cash-only. 


Check out a comedy show


Chicago's reputation as a comedy town is well deserved, and comedy clubs dot the city's map. You can see excellent live shows every night of the week, but Second City, iO and the Annoyance are always safe bets. Laugh off your first date jitters at one of these stellar institutions. 


Geek Bar
Photograph: Martha Williams

Try your luck at a board game bar


Sometimes you need another thing to talk about other than the basic fist date chit-chat. That's where a board game bar can be a lifesaver. Play a game of Connect Four or Sorry while getting to know each other—for your own sake, maybe Risk isn't a wise choice for a first date. Check out this list of board game bars in Chicago for a playfully competitive first date.

cameron's, best ice cream, ice cream
Photograph: Jaclyn Rivas

Go out for ice cream


C'mon, no one's too old (or too cool) for ice cream. Whether it's custard, gelato or frozen yogurt that strikes your fancy, Chicago has great ice cream shops serving up a perfect version of the icy dessert. We're crazy about the custard at Scooter's, the towering cones at Original Rainbow Cone and the inventive flavors served up at Jeni's. 


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