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Date nights. Remember those? They used to involve leaving your house—and now they’re back in full swing. If you’re at a loss as to where to take your sweetheart out on the town—after all, remembering how to put on hard pants is difficult enough—let our list of the best Chicago date night ideas put your mind (and your planner) at ease. Luckily, the Windy City has it all, from comedy to architecture to art and (inevitably) to Malort, so you’ll easily find something to suit the tastes of you and your boo.

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1. Avondale Bowl

Fans of @accidentallywesanderson, this one’s for you. Avondale Bowl opened in January of 2020, so chances are the pandemic kept you away from this thoroughly picturesque, and vintage-inspired spot. Make up for lost time with ample photo ops, a few glasses of The Messenger cocktail (think: a walnutty old fashioned) and the joys of hand-scoring on scorecards designed by popular local artist Ryan Duggan.

3118 N Milwaukee Ave.; avondalebowl.com

Where to eat: Cafe Con Leche offers a mix of indoor and outdoor seating, where you can enjoy ceviche, jibaritos and ropa vieja.

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2. Art Institute of Chicago

The Art Institute of Chicago is a classic date spot for a reason: it’s sure to impress, thanks to its status as one of TripAdvisor’s best museums in the world, and it’s so vast that there’s always something new to explore—even more so when traveling exhibitions come and go. To that end, the Obama Portraits by Kehinde Wiley and Amy Sherald—here on loan from the Smithsonian—are well worth the hype (and long lines). But while you’re there, don’t sleep on the Bisa Butler exhibit, where images of Black life are portrayed in intricate, vibrant quilts.

111 S Michigan Ave.; artic.edu

Where to eat: Walk 1.5 blocks from the museum to Miller’s Pub, where you can enjoy thoroughly strong drinks (try the Gibson) alongside baskets of freshly deep-fried Wisconsin cheese curds.

3. Loop Mural Walk

The Loop Mural Walk features art from local and international artists, stunning Chicago architecture as far as the eye can see, and plenty of flexibility, as you can choose from three suggested routes for your self-guided tour. If you feel like showing off for your date, opt for the “very challenging” Northeast Loop Murals route, which challenges you to spot seven murals over the span of about five blocks, ending outside the Chicago Cultural Center. (And if you don’t then duck inside to check out the Tiffany dome, what are you even doing?)

Where to eat: Depending which route you choose, the best dining option may vary. But if you end your route toward the north of the Loop, you can easily hop up to Pops for Champagne, a speakeasy under Watershed, where you can enjoy regionally brewed beers and mini lobster rolls.

4. Pilot Project Brewing Beer Fest

Pilot Project Brewing, an independent brewery incubator in Logan Square, is hosting its first annual festival on August 8 from 12 p.m. to 4 p.m. Buy a wristband and get ready to sample suds from a dozen brewery start-ups, such as Azadi Brewing Company, Histrionic Brewlab, and others, whose goods include cider and hard kombucha in addition to beer.

2140 N Milwaukee; pilotprojectbrewing.com

Where to eat: The festival is also hosting a pig roast, but if that's not your vibe, take a six-minute walk to 90 Miles Cuban Cafe to enjoy salmon with mango chimichurri on the spacious patio.

5. Chicago Dogs Baseball Game

You don’t have to go all the way to Milwaukee to enjoy baseball stadium antics like the Brewers’ famous 7th-inning sausage race. Instead, hop over to Rosemont’s Impact Stadium to cheer for indie pro baseball team the Chicago Dogs, whose player roster includes former Cubs, and whose mascots include fuzzy, lovable Squeeze (a mustard bottle) and the dastardly Ketchup. (Ketchup? Near a Chicago hot dog? Get outta here.) Check out this season’s game schedule here.

9850 Balmoral Ave., Rosemont; thechicagodogs.com/explore-impact

Where to eat: You really can’t beat the food already on the Chicago Dogs premises, which includes classics like hot dogs (duh!), nachos, and plenty of cold beer, all at prices lower than what you’ll see at a larger ballpark.

6. Movies in the Park

The Chicago Park District’s Movies in the Park series has returned for 2021, and our picnic blankets have never been more excited to hit the town. The schedule runs through mid-September and reaches practically every corner of the city; we’re especially excited about Jurassic Park at Wentworth Park (July 22) and The Wiz at South Shore Cultural Center (September 9).

Where to eat: If you take our recommendation for Jurassic Park at Wentworth Park, try some Salvadoran pupusas from Pupuseria, or grab some plant-based treats at Majani Restaurant on your way to South Shore Cultural Center.

7. The Newport Theatre

This 125-seat theater above Links Hall in Wrigleyville hosts drag, burlesque, and variety shows selected by Artistic Curator (and lauded local burlesque performer) Eva La Feva. Sip a craft beer while enjoying upcoming shows, such as The Embodiment, an interactive variety/burlesque showcase, and the Songs to Caftan In album release show from Chicago vaudevillian Plucky Rosenthal.

956 W Newport Ave., newporttheater.com

Where to eat: Dig into empanadas, arepas, and other Venezuelan specialties at Bolivar and Lincoln, which is a scant three-minute walk from the theater.

8. Robie House & Seminary Co-Op Bookstore

Fellow nerds, here’s one for you: why not spend an idyllic Hyde Park afternoon touring Frank Lloyd Wright’s Robie House before browsing the shelves at Seminary Co-Op Bookstore? Make your sweetheart swoon with your appreciation for Wright’s Prairie School designs and your taste in books, all in one fell date swoop.

5757 S Woodlawn; flwright.org/tours/robie and 5751 S Woodlawn; semcoop.com

Where to eat: Walk up to 55th street to eavesdrop on University of Chicago students and professors at Woodlawn Tap—or just drift from the bookstore into the adjacent Plein Air Cafe for a prosciutto and Manchego baguette with fig jam.

9. Chicago Magic Lounge

Andersonville’s Chicago Magic Lounge is reopening at last (on August 2), so you and your date can enjoy a combination of close-up magic at your table between larger-scale shows onstage when you purchase tickets for The Signature Show, which the theater describes as “an homage to the heyday of Chicago-style magic.” Whether you opt for The Signature Show or other entertainment from the calendar, don’t forget to take your phone with you to the bathroom, where you can take an amusing selfie on the trompe l’oeil floor (trust us).

5050 N Clark St.; chicagomagiclounge.com

Where to eat: When you’re this close to Hopleaf, it’s hard to remember anywhere but Hopleaf exists. And that’s just fine, because once you reacquaint yourself with the extensive list of Belgian beers and fragrant, brothy bowls of mussels, the rest of the world feels far away, indeed.

10. Comedy Open Mic at Cole’s Bar

You’re just as likely to see a newbie ask the crowd, “Is this thing on?” as you are to see celebs like Hannibal Buress drop by the open mic at Cole’s Bar (which the Chicago Tribune named as the best in the city in 2019). And it’s that mix of slam dunks and new experiments that makes this open mic so much fun; you and your date will always have something to giggle about.

2338 N Milwaukee; colesbarchicago.com

Where to eat: After downing so many well-priced drinks at Cole’s, proximity is a key factor in seeking out food after the show (or for establishing a base layer before hitting the sauce). Pop around the corner to Boiler Room, whose namesake slice features PBR-marinated meatballs and plenty of piquant giardiniera.

11. Carol’s Pub

Carol’s is back open at last, and we’re all the better for it (until we wake up the next morning, that is). This famously festive country-western spot serves Chicago Handshakes (Old Style and a shot of Malort) and smashburgers until 2 a.m. on the weekends, so you’ll have plenty of time to dance to live music all night long. Pop in on a Tuesday instead, however, and you can take the stage yourself for karaoke, or just catch a rowdy round of bingo. (See the full calendar here.)

4659 N Clark St.; carolschicago.com

Where to eat: See above re: burgers, but if Carol’s pub food isn’t your jam, pre-game at Anna Maria Pasteria for a plate of cheese tortellini alla vodka or chicken piccata.

Chicago Date Night Ideas Tour of Graceland Cemetery
ShutterRunner.com (Matty Wolin)/Getty Images

12. Tour of Graceland Cemetery

Graceland Cemetery is a pastoral Victorian resting ground that’s home to Ernie Banks, Daniel Burnham, Mies Van der Rohe, and other notable Chicagoans. But beyond the gorgeous mausoleums and gravestones—there are over a hundred of them to admire—Graceland is also an arboretum, which makes it an especially picturesque spot in the summer and autumn months. Whatever your main focus, you have plenty of options: a free, self-guided tour; a tour with help from a $10 guide at the cemetery’s main office, or tours organized by the Chicago Architecture Foundation or Chicago History Museum. You can see all of your choices here.

4001 N Clark St.; gracelandcemetery.org

Where to eat: Grab a seat at the sidewalk cafe at Uncommon Ground, where string lights twinkle above plates of steak frites, margherita flatbread with spent-grain dough, and glasses of mead-sweetened sangria.

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