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Photograph: John Khuu

The 12 most interesting date ideas in Chicago

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

By Emma Krupp

It doesn't matter if you're single or in a long term relationship—planning a date that's a little out of the ordinary can be difficult. Sure, you could grab dinner at one of the best restaurants in Chicago, but sometimes it's nice to do something that doesn't involve sitting across one another at a table. That's why we've rounded up some more creative options (with current safety restriction in mind) for you and your prospective or current partner. Explore Chicago attractions, show off your axe-throwing prowess or wander through some of the best art galleries in Chicago. For your romantic consideration and inspiration, here are a few unique date ideas in Chicago.

RECOMMENDED: Check out the most romantic places in Chicago

Unique date ideas in Chicago

16th Street Murals Pilsen
Photograph: Time Out/Zach long

1. Stroll along the 16th Street Murals

Art Public art Lower West Side

Stretching from the Chicago River to Western Avenue in Pilsen, the walls of an old railroad embankment host a vibrant and evolving outdoor gallery of murals by prominent and emerging artists. Impress your date by pointing out some of your favorite artworks as you move across 16th street, whether you prefer colorful creations by revered local artists like JC Rivera and Hebru Brantley or the contributions from international street artists such as ROA and Sheryo.

Photograph: Courtesy Bad Axe Throwing

2. Hit a bullseye while axe throwing

Things to do Sport events 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.

garfield park conservatory
Photograph: Time Out/Jaclyn Rivas

3. Get lost inside the Garfield Park Conservatory

Attractions Parks and gardens East Garfield Park

Looking for a cheap date idea? The Garfield Park Conservatory is free and open 365 days of the year (though you'll need to make an advance reservation and donations are welcome). 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 and check out prehistoric ferns.

Photograph: Courtesy Matthew Rachman Gallery

4. Tour Chicago Avenue's best art galleries

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. Just keep in mind that many galleries are requiring reservations in advance of your visit—you'll likely have to do some planning.

Photograph: Max Herman

5. See an indie movie at the Music Box

Movie theaters Independent Wrigleyville

You and your date could see the latest blockbuster at the multiplex, but you're likely to find something a bit more thought-provoking being screened at this beloved arthouse theater. Now that the Music Box has reopened at limited capacity, you can see everything from foreign films to indie documentaries on the big screen. And if you'd rather watch something at home, the Music Box has its own streaming platform.

Metropolitan Brewing
Photograph: Tracy Hurst

6. Have a beer by the river

Bars Breweries Avondale

Not quite ready to have a drink indoors with your date? Not a problem. Metropolitan Brewing has kept its patio open throughout the winter, serving German-style beers with a view of the Chicago River just outside of its Avondale taproom. Tables are first-come, first-served, but you're not likely to encounter much of a wait when the mercury is low. If you get too chilly, cozy up beside your date instead of sitting across from them!

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

7. Watch the Neo-Futurists perform 30 plays in 60 minutes

Theater Interactive Uptown

While you can't actually take your date to the the Neo-Futurarium right now, you can can cuddle in front of a laptop and watch the Neo-Futurists' signature show. Anyone who support's the theater's Patreon has access to a streaming version of Infinite Wrench, which usually crams 30 miniature, two-minute plays into a 60-minute show that bristles with madcap energy. You might witness a dramatic monologue, a funny song or simply stare at someone eating a sandwich.

606 Records
Photograph: Drew Mitchell

8. Explore your shared musical tastes at 606 Records

Shopping Music and entertainment Lower West Side

You don't have to enjoy the same music as the person you're dating, but it helps to have a few genres or bands in common. Stock up on some tunes that you can listen to together at 606 Records, where you'll find classic rock and soul LPs alongside releases from adventerous local and international labels. Perhaps a Numero Group compilation or a Mr Bongo reissue could be the perfect soundtrack for your next dinner?

Bahá’í House of Worship
Photograph: Eric Allix Rogers.

9. Take a long walk on the North Shore Channel Trail

Attractions Sightseeing Lincoln Square

You could sit around and idly chat with your date or you could get some exercise and see some beautiful scenery along the way. The North Shore Channel Trail follows the Chicago River north to Evanston, with plenty of worthwhile stops along the way. Depending on how far you're willing to go (you'll probably make it farther on a bike), you could swing by Lincolnwood Town Center, admire the art at Skokie Northshore Sculpture Park or end up at the Bahá'í House of Worship in Wilmette.

Rock Island Public House drive-in
Photograph: Courtesy Rock Island Public House

10. Head to a DIY drive-in movie theater

Restaurants Suburbs

If you have access to a car and you're willing to venture just outside of city limits, this could be the night out for you. Rock Island Public House hosts first-come, first-served drive-in movie screenings on Friday, Saturday and Sunday evening—you might catch a classic horror film, a cult classic or a beloved comedy (check the website for a complete schedule). Order some drinks and a bite to share and try to pay attention to the movie... or don't!

Monarch Thrift Shop
Photograph: Courtesy Monarch Thrift Shop

11. Go bargain hunting at Monarch Thrift Shop

Shopping Thrift stores Avondale

Find a new outfit or browse used books together at this beloved Avondale thrift store, where proceeds benefit addiction recovery, and those experiencing homelessness. Make an appointment for two on the Monarch Thrift Shop website and then show up ready to find some deals on all sorts of gently-used items.

Photograph: Brendan Lekan

12. Share some smoked shrimp at Calumet Fisheries

Restaurants Seafood South Deering

What's more romantic than traveling to the edge of Illinois to enjoy some smoked fish from this beloved shack? Calument Fisheries has been serving catfish, shrimp and salmon for more than 70 years. It's a takeout-only business, so you'll need to grab your brown paper sack of grub and find a spot to share it, whether in your car or on the 95th Street bridge that famously appeared in the Blue Brothers.

Want to take your date to dinner?


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