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The 17 most unique date ideas in Chicago

Surprise and delight your special someone with these fabulous date ideas in Chicago

Photograph: John Khuu
By Emma Krupp and Morgan Olsen |

Singles and long-term couples alike know that brainstorming creative date ideas can range from tedious to excruciating, depending on the willpower and decisiveness of the parties involved. While grabbing dinner at one of the best restaurants in Chicago is always a solid option, we're begging you to hit the refresh button on date night. Why not cruise the Chicago River, explore amazing Chicago attractions, hang out at a dog park, or wander through some of the best art galleries in Chicago? In a city like ours, the options are nearly endless. For your romantic consideration, here are our picks for the most unique date ideas in Chicago.

RECOMMENDED: Check out the most romantic places in Chicago

Unique date ideas in Chicago

Bahai Temple
Photograph: Eric Allix Rogers
Attractions, Religious buildings and sites

Plan a picnic at the Bahá'í House of Worship


The Bahá'í House of Worship in Wilmette is a sight to behold, which makes it a perfectly unique destination for your next date. After strolling the pristine grounds and scoping out the intricate, domed temple, plop down for a picnic near one of the reflection pools. Just be sure to pack a blanket and lunch treats for you and your date.

Humboldt Park
Photograph: Jaclyn Rivas
Things to do

Glide around in a swan-shaped boat

Humboldt Park

Did you know that swans mate for life? You may not be trying to get hitched, but the elegant birds nonetheless make for pretty symbol of romance, especially in boat form. From May until September, you can take a swan boat for a cruise on the Humboldt Park Lagoon for just $11 an hour. Paddle around for a while, then take a leisurely stroll to soak in the Prairie-style architecture of the park's historic boathouse. 

Photograph: Courtesy Matthew Rachman Gallery
Art, Galleries

Tour Chicago Avenue's best art galleries

River West/West Town

The stretch of Chicago Avenue bounded by Ashland Avenue and Wood Street is home to some of the city's best, most innovative galleries, providing the opportunity for a very manageable (and not to mention, free) walking art tour. Start at Matthew Rachman Gallery, which showcases sleek mid-century furniture and contemporary art, then head due west. You'll find other gallery standouts like DOCUMENT, Rhona Hoffman Gallery, Volume and more along the way. 

Adler planetarium, solar system
Photograph: Nick Ulivieri
Museums, Science and technology

Stargaze at the Adler Planetarium

Museum Campus

Date ideas hardly get more romantic than stargazing with your sweetheart. Take in the sparkling night sky all year round at the Adler Planetarium’s Grainger Sky Theater. Several projectors plaster footage of the night sky all over the massive 36-foot dome, transporting you to other planets, constellations and solar systems. It’s a total “wow” moment.

Photograph: Courtesy Wendella

Hitch a ride to Chinatown on the water taxi

Sure, you could get to Chinatown via a number of transportation options throughout the city, but we think a ride on a water taxi is a decidedly nicer route than any old bus or train. You can hop on one of the bright-yellow boats from several downtown stops, including Michigan Avenue and Union/Ogilvie Stations; the boat will then take you on a 15- to 30-minute cruise downstream. Once you've docked in Chinatown, the neighborhood is your proverbial oyster—we recommend grabbing bubble tea and checking out some of the city's best dim sum spots.  

Photograph: Courtesy Bad Axe Throwing
Things to do, Sport events

Hit a bullseye while axe throwing

West Loop

Axe throwing—which, seeing as it involves hurling an axe at a wooden target, is sort of like the Canadian lumberjack version of darts—has surged in popularity over the past couple years, but don't discount it as a novel (if slightly intense) date option. Bring some snacks and non-alcoholic beverages along to lighten the mood as you test who has the better arm, and be sure to visit the company's website to check for walk-in availability at either of two Chicago locations. 


57th Street Books
Photograph: Courtesy of 57th Street Books
Shopping, Bookstores

Be bookworms at 57th Street Books

Hyde Park

If you're way past the introductory questions (where are you from? What do you do? What's your family like?), enjoy each other's silence at 57th Street Books in Hyde Park. The sprawling but cozy shop is lauded for its noteworthy selection of local authors, so grab a tome and stay awhile.

Photograph: Marc Monaghan for the John D. and Catherine T. MacArthur Foundation
Theater, Interactive

Watch 30 plays in 60 minutes at the Neo-Futurarium


You never know what you'll see when you attend the Neo-Futurists' signature show, Infinite Wrench, but it's nearly always entertaining. The ensemble races against the clock to cram 30 miniature, two-minute plays into a 60-minute show that bristles with madcap energy. Over the course of the evening, you might witness a dramatic monologue, a funny song or simply stare at someone eating a sandwich. 

Photograph: Hallie Duesenberg
Shopping, Design and interiors

Go antique hunting at Randolph Street Market

West Loop

You don't have to live together to shop this monthly, European-style vintage market in the West Loop. In the summer months, the bazaar is held outside, offering a parking lot full of furniture, clothing and home goods in the sunshine. Come winter, the market moves inside Plumbers Hall, allowing shoppers to browse without freezing their butts off. Learn more about your partner's style as you peruse the massive shopping event. 

Photograph: Jaclyn Rivas
Attractions, Parks and gardens

Get lost inside the Garfield Park Conservatory

East Garfield Park

Looking for a cheap date idea? The Garfield Park Conservatory is free and open 365 days of the year (though a small donation is encouraged at the door). Once inside, you and your date can explore rooms that are filled to the brim with different plant species. Admire towering palm trees, take a photo in the Desert House, roam the outdoor gardens and check out prehistoric ferns.

Joey Cranford
Photograph: Jaclyn Rivas

Catch a show at Chicago Magic Lounge


Pay homage to Chicago's magic-steeped history at this Ravenswood lounge that boasts three performance spaces including the front bar, the Blackstone Cabaret mainstage and the intimate 654 Club. The interactive performers will have you and your date laughing in no time, easing those early-date jitters. As an added bonus, you can check out "Music & Magic" shows, which feature a live jazz band, on Mondays for $20 per person.

Photograph: Alex Steyn on Unsplash
Things to do

Pet some fluffers at the Montrose Dog Beach


Who needs the Westminster Dog Show when you can peep an untold number of pups running around the beach for free? The fenced-off portion of Montrose Beach is dedicated to dogs and their owners, but we bet you and your date could pet a friendly doggo or two with permission from their owners (and if all else fails, there's no harm in dog watching for a while). 

Sleeping Village
Photograph: Christopher Dilts

Grab $1 beers at Sleeping Village


Part bar, part music venue, Sleeping Village has a little something for everyone in Avondale. Beyond offering dirt-cheap concert tickets (we're talking $10 and under for a ton of shows), the lounge also hosts weekly $1 Beer Nights, a series that'll make your wallet and your date happy. In exchange for $5 at the door, you can enjoy music from up-and-coming artists and cash in on select $1 brews. Keep an eye on Sleeping Village's calendar for specials. 

Field Museum lobby
Photograph: Courtesy the Field Museum
Things to do

Take advantage of a free museum day

Did you know that you can take in masterpieces at the Art Institute of Chicago and gaze at tropical fish while strolling through Shedd Aquarium without spending a dime? With a little planning and some research, Illinois residents can enjoy free museum days at some of the city's top institutions. Browse upcoming free days or visit and always-gratis museum or zoo whenever you please. 

Photograph: Jeremy Atherton
Things to do

Go on a bar crawl along the Chicago Riverwalk


The Chicago Riverwalk is dotted with excellent bars and restaurants, cozy lookout points and awesome city views—all the trappings of a perfect date night. Grab a glass of vino at City Winery, sip tiki drinks at Island Party Hut, share nachos at Tiny Tapp & Cafe and finish the night at Frost Gelato.

Photograph: Neal O'Bryan
Sports and fitness, Baseball & softball

Snag bleacher seats at Wrigley Field


Wrigley Field is one of those essential summertime attractions that unsurprisingly doubles as an awesome date night destination. Order a Bavarian pretzel, two pints of beer and get ready to root, root, root for the home team together.

Photograph: Jaclyn Rivas
Attractions, Parks and gardens

See a free movie at Millennium Park

Millennium Park

When summer weather descends on Chicago, most residents want to spend as much time as possible outside in the sunshine. Rather than planning a trip to the movie theater, take advantage of Millennium Park's free summer movie series, which takes over Pritzker Pavilion Tuesday nights from June through August. Don't forget to pick up snacks and a bottle of wine—the park allows guests to bring their own food and booze for the series.

Want to take your date to dinner?