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Published September 1, 2023

The Best Unexpected Date Ideas in Chicago

Say no to boring dates! It's time to spice things up with these 15 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. We've curated a selection of unconventional date ideas in Chicago that will hype your experiences and provide endless inspiration.

Be prepared for the mind-boggling magic shows or dive into the whimsical world of cat arcades. With this collection of unique and beloved date suggestions, you'll ensure year-round fun and create unforgettable memories together.


15 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


Enjoy a Secret Omakase Experience Hidden in a Swanky Hotel

Tucked away in an upscale suite in Hotel Lincoln is Sushi Suite, a speakeasy-style omakase experience waiting to welcome discerning sushi connoisseurs. Once you find the suite, a private sushi chef will whip up a 17-piece omakase tasting for a dining experience you won鈥檛 forget! You can even add on a craft cocktail flight, with curated libations sure to pair perfectly with the chef鈥檚 sushi masterpieces.

Where: 1816 N Clark St, Chicago, IL 60614
More information.


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


Grab Drinks at 90s Speakeasy Bar

Back 2 the Video Store is a new pop-up bar throws it back to a time when visiting the video store to choose a Friday night flick was an experience in and of itself. From lava lamps to pog-playing stations, you'll be surrounded by 90s nostalgia, but the best part is the movie-themed cocktails. Instead of browsing videos to rent, you'll be choosing cocktails inspired by your favorite films from decades past.

Where: 1365 N Milwaukee Ave., Chicago, IL
More information.


1365 N Milwaukee Ave, Chicago, IL 60622, USA
Back 2 The Video Store: A 90s Speakeasy Bar - Chicago
Starting at $20

Book now


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
More information


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

Book now


See a Drive-In Movie

Experience the magic of a bygone era at a drive-in movie! Cuddle up under the stars and catch timeless classics or the latest blockbusters while sharing tacos and beers from the bar and grill. With a stellar lineup and Chicago's skyline as the backdrop, it's a classic twist on the standard movie theater experience.

Where: 2343 S. Throop Street, Chicago, IL
More information.

2343 South Throop Street, Chicago, IL 60608, USA
ChiTown Drive-In
Starting at $33

Book now


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
More information.


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


Practice your Swing at Five Iron Golf

Whether you and your date are beginners or experienced golfers, there's fun for everyone at Five Iron Golf, an indoor golf simulator with several locations in Chicago. Practice your skills on the virtual driving range or course simulator, or challenge each other to a competition with a selection of other exciting virtual games.

Where: Various locations.
More information.


Relax & Rejuvenate at AIRE Ancient Baths

Prepare to pamper yourselves at this one-of-a-kind spa in River West, where you and your date will go on a relaxation journey via their signature Ancient Thermal Bath Experience. During your visit, soak away your stresses in the traditional Roman, Greek, and Ottoman-style baths (with temperatures ranging from 102潞F to a chilly 50潞F!), try the aromatherapy steam room, or take a swim in the heated indoor/outdoor pool. Add a couples massage or a wine bath for two for a truly luxurious experience.

Location: 800 West Superior St., Chicago, IL 60642
More information.


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.
More information.


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
More information.


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.


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, Illinois 60622
More information.


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



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