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Published January 2, 2024

The Best Unexpected Date Ideas in Chicago

Say no to boring dates! It's time to spice things up with these unique date ideas in Chicago. 馃敟

by Chicago Bucket List

Discovering your perfect match can be quite a journey, but the process of dating doesn't have to be a dull affair. Bid farewell to the repetitive routine of happy hour or dinner dates and inject some excitement into your romantic rendezvous.

Whether you need a slam-dunk first date idea or are looking to get out of the Netflix and chill routine with your long-term partner, we've curated a selection of unconventional date ideas in Chicago that actually make dating, well, fun. After all, life is just too short to waste any more time on boring dates.


20+ Unique Date Ideas in Chicago

Catch Live Jazz in a Hidden Speakeasy

Head to Dorian's in Wicker Park, where you'll enter a record shop and make your way to a door leading to a hidden cocktail bar with live performances and vinyl DJ sets over Hi-Fi Italian sound. It's the perfect laidback date night spot with a cozy, moody interior, unique cocktails, and the lyrical sounds of live jazz music.

P.S. See our roundup of Chicago's best hidden speakeasies here.

Where: 1939 W North Ave. Chicago, IL
More information.


Dorian鈥檚, 1939 W North Ave, Chicago, IL 60622, USA
Live Jazz Nights at Dorian's
Starting at $20

Book now


Create a Graffiti Masterpiece

Looking for a fun and unique way to tap into your creativity? Get ready to grab some spray paint and unleash your inner street artist at an Urban Art Workshop. This interactive workshop will allow you to create your own original piece while getting acquainted with the ins and outs of working with spray paint and stencil application. At the end of the workshop, you get to take your canvas home!

Where: Chicago Kedzie Plaza- 800 N. Kedzie, Chicago IL 60651
More information.

800 N Kedzie Ave, Chicago, IL 60651, USA
Spray Paint 鈥榥鈥 Sip series
Starting at $40

Book now


Have Date Night With a View at Offshore Rooftop

Offshore Rooftop offers a date night package that includes a guaranteed spot at one of the best tables in the house with a breathtaking view. Choose from a Charcuterie Board with two glasses of bubbles or a Chocolate Fondue Board with two Espresso Martinis. Or maybe just book both because deciding between the two sounds too hard.

Where: Offshore Rooftop: 1000 E Grand Ave, Chicago, IL
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1000 E Grand Ave, Chicago, IL 60611, USA
Date Night With A View at Offshore Rooftop
Starting at $51

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Hang With Some Kittens at Catcade

Arcade games and cute cats? Hello, perfect date spot! Catcade is part arcade, part lounge, and part animal rescue. You and your date can challenge each other to a few rounds of classic arcade games like Pacman, and even if you lose, you can console yourself with a cuddly kitten. As a bonus, all the cats are available for adoption, so if you fall in love with a furry friend, they might just come home with you! Reservations are highly recommended.

Where: 1235 W Belmont Ave, Chicago, IL 60657
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Brew Up Cocktail "Potions" at The Cauldron

The Cauldron is a wizard-themed bar and restaurant set inside an old bank with an iconic vault and hosts a number of fun and magical events. Try a Potion Mixology Class, where you'll start with a bubbling shot and one welcome drink poured from a magic wand. Then, brew two molecular cocktails or non-alcoholic "potions" using a magic wand provided by The Cauldron.

Where: The Cauldron Chicago: 1612 W Division St, Chicago, IL
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The Cauldron Chicago, 1612 W Division St, Chicago, IL 60622, USA
Potion Mixology Classes at The Cauldron Chicago
Starting at $42

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Sip Wine and Listen to Live Music at Bordeaux

This wine bar in Roscoe Village has all the elements of a perfect romantic date鈥攇ood food, great wine, and live music. Bordeaux showcases some of the best wines from its namesake, Bordeaux, France, along with fine wines from Italy, Spain, Greece, Turkey, and more. They also regularly feature live jazz and classical musicians, so stop in for a bite and treat yourselves to a few glasses of wine while you listen to live music.

Where: 2147 W. Roscoe Street 1E, Chicago, IL
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Try Your Hand at Curling

For some low-stakes competition, check out Stone鈥檚 Throw at The Emily Hotel. This spot features four curling courts, a curated menu of winter beverages and snacks, and heated firepits. Located on the fifth-floor terrace of the hotel, this out-of-the-box experience is perfect for a winter date night. Loser has to treat their date to a round of warm cocktails!

Where: The Emily Hotel: 311 N Morgan St, Chicago, IL
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Take a Pizza Making Class with Wine

Spend a romantic evening making handmade Neopolitan pizzas and sipping on your choice of beer and wine at this DIY Pizza and Sip class at Millennium Hall. Choose from a number of toppings, sauces, meats, and cheeses, and then make a selection from the open bar while you enjoy some quality conversation and one-on-one time. When the pizza is ready, you can choose to take it home or indulge together at the restaurant.

Where: Millennium Hall: 11 N Michigan Ave, Chicago, IL
More information

11 N Michigan Ave, Chicago, IL 60602, USA
DIY Pizza & SIP
Starting at $59

Book now


Laugh the Night Away at a Stand-Up Comedy Show

Head to the Laugh Factory, one of Chi-town鈥檚 most popular comedy clubs, for an unforgettable night out. With showcases of 5-7 comedians performing every night, from some of the biggest names in comedy to local comedians, you're sure to find a show that will make you laugh until your stomach hurts.

Where: 3175 N Broadway, Chicago, IL 60657
More information.

Laugh Factory, North Broadway, Chicago, IL, USA
Laugh Factory
Starting at $15

Book now


Play Indoor Mini Golf

Show off your putt-putt skills at Big Mini Putt Club. The 5,000-sqft space was once a garment manufacturing building but is now home to a challenging, fun mini golf course for all abilities and skill levels. Make sure to visit the bar for beer, cider, cocktails, mocktails, and more!

Where: 1302 N Milwaukee Ave, Chicago, IL
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Discover a New Museum

Chicago is home to dozens of fantastic museums. You've probably been to the big ones鈥攖he Art Institute, the Field Museum, the Shedd Aquarium (if you haven't yet, GO)鈥攂ut there are lots more places to discover. The Richard H. Driehaus Gallery of Stained Glass at Navy Pier features stained glass wonders from local institutions (there's even one of Michael Jordan), and it's free to visit. Take a tour of literature through the decades at The American Writers Museum, or visit the oldest home in Chicago, the Noble Seymour Crippen House.

P.S. Looking to save? Check out our guide to Chicago's free Museum Days in 2023.

Where: Various locations.
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See a Speakeasy Cabaret Show

Dinner and a show is a classic date night combo, but few places do it better than Bordel. The Parisian-inspired speakeasy has nightly music and entertainment, from jazz musicians to burlesque performers to high-profile DJs. Grab a bite to eat and soak up the ambiance鈥攖hink pink velvet sofas and drapes, tasseled chandeliers, vintage bronze sconces, and custom, handcrafted wallpaper鈥攖hen sit back with a cocktail and enjoy the show.

Where: 1721 W Division St, Chicago, IL
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Stroll Along the 16th Street Mural Wall

For a fun and free date idea, take a stroll down the 16th Street Mural wall, a two-mile embankment covered with more than fifty ever-changing murals painted by top street artists. After you鈥檝e worked up an appetite with your adventure, stop by one of the Pilsen neighborhood鈥檚 many bars or restaurants to discuss your favorite murals over a bite to eat with your date.

Where: 922 W. 16th St., Chicago, IL; the wall runs from 16th St from Halsted St west to Western Ave
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Share Fondue at Geja鈥檚 Cafe

For a unique, interactive dinner experience, head to Geja鈥檚 Cafe to share a lavish fondue meal together. Here you can choose from a variety of options ranging from a classic Swiss-gruyere cheese fondue all the way up to decadent options like beef tenderloin, cold water lobster tail, and scallops. For dessert, definitely don鈥檛 skip the cafe鈥檚 famous Belgian chocolate fondue, served tableside with marshmallows.

Where: 340 W Armitage Ave, Chicago, IL 60614
More information.


Check Out Drunk Shakespeare

Imagine trying to watch a classic Shakespearean tragedy, and one of the cast members is trying to perform while plastered. That's the premise of Drunk Shakespeare, and as you can imagine, it makes for a hilarious night out. The stage is set in a hidden library, and every show is different depending on who is drinking...and what they're drinking. Anything can happen!

Where: The Lounge at The Lion Theatre: 182 North Wabash Ave, Chicago, IL
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The Lounge At The Lion, 182 N Wabash Ave, Chicago, IL 60601, United States
Drunk Shakespeare at The Lounge at The Lion Theatre - Save 49% !
Starting at $25

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Go on a Chicago Architecture Cruise

Taking an architecture cruise is a Chicago must-do whether you're a tourist or not. You'll enjoy taking in the iconic skyline and learning a little more about the city any time of day, but an evening cruise down the river is perfect for date night. Grab dinner first, then spend the evening watching the city light up.

Where: 401 N. Michigan Avenue, 60611, Chicago
More information.

401 North Michigan Avenue, Chicago, IL 60611, USA
Chicago Architecture River Cruise
Starting at $27

Book now


Play Games at a Board Game Bar

No one likes a date that's just there to play games...unless they're literal about it. Enjoy some good old-fashioned fun at one of Chicago's various game bars and cafes. Snakes & Lattes, KibbitznestBonus Room Game Cafe, are all great places to play classics like Scrabble, Rummikub, Guess Who? and more. If board games aren't your thing, try Game Room or Guthrie's Tavern for games like skeeball, billiards, shuffleboard, chess, and checkers.

Where: Various locations.


Take a Swan Boat Cruise in Humboldt Park

Head to scenic Humboldt Park for a romantic vintage swan boat cruise on the park鈥檚 lagoon. After paddling to your heart鈥檚 content, grab a bite to eat at the similarly retro-inspired Spinning J Bakery and Soda Fountain, serving up gelato, shakes, and other soda fountain classics just outside the park.

Where: 1301 North Humboldt Drive, Chicago, IL
More information.


The Best Restaurants for Group Dinners in Chicago
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