Chicago

Chicago’s Coolest and Most Romantic Summer Date Ideas

It’s getting hot in here.

Let’s face it: Lockdown didn’t make dating easy. Turns out, trying to court suitors during a pandemic isn’t exactly a walk in the park. But now that you can literally walk in the park again, it’s fair to say that we’re all eager to make up for lost time. 

Can you feel it in the air tonight? It’s not just the weather that’s heating up across Chicagoland—summer romance is sizzling. If you’re single and trying like hell to mingle, this town is more than willing to play host. And even if you’re already shacked up with a significant other, you’re undoubtedly ready to enjoy a date night that ventures beyond your own living room. That’s why we put together this ingenious list of Chicago-centric date ideas to inspire a little passion as we all work our way back out into the world. Grab your sexiest face mask, snag a sweetheart, and get your game on.

Splurge on a luxury staycation 

When a full-on excursion feels too costly—or like too much of a commitment—nothing sets the mood quite like a properly staged staycation. In any normal year, Chicago attracts as many as 60 million visitors, so you might as well try and tap into what they’re all coming to see. That’s where the Langham comes in. The five-star hotel perched just north of the river is offering a summertime Chicago Architecture package that ought to appeal to locals and tourists in equal measure. In addition to luxe accommodations backdropped by some of the city’s finest views, you’ll score two tickets to the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady. Date night, done.


Within the Loop, you can lap up local flavors at the Kimpton Gray. The landmark property is serving up bottled cocktails at check-in—all conceived by neighborhood bartenders with portions of the proceeds benefiting service industry professionals affected by the pandemic. Cart a few up to your suite and pregame in one of their outsized vessel tubs. Then button down your finest floral print linens for a festive evening at Boleo. Inspired by Peruvian and Argentinian street food and South American cocktail culture, it’s a boisterous outpost carved into the hotel’s 15th floor rooftop.

Flex that vax card at a top-notch restaurant

The restaurant industry is just now emerging from its most challenging year in memory. But against all odds, here in Chicago, hospitality is coming back strong and showcasing its A-game for all to see. If you’re wining and dining, options are robust. Impress your special someone by copping an outdoor table at Chicago date night institutions like Restaurant Row’s aptly named The Darling, Lincoln Park stalwart Avli Taverna, or River North stunner RPM Seafood. Thinking about throwing a known aphrodisiac into the mix? We’ve got all your Chitown oyster bar needs covered right here


And definitely don’t sleep on some of the notable newcomers entering the fray. Top Chef alum Joe Flamm just landed in the dense West Loop landscape with Rose Mary: A convivial, open-kitchen affair specializing in a smattering of trans-Adriatic cuisine. A well-conceived list of wines showcases fun (read: funky) offerings that practically jump out of the glass. If you’re craving something more traditional, consider Robert Et Fils. The intimate North Center French bistro debuted amidst the pandemic with take-out service, and after opening the patio in May, couples can now immerse themselves in what executive chef Rob Shaner dubs “Parisian drinking fare.”

Soak up the scenery on a sundrenched weekend getaway

Have car, will travel. Pack your sandals and beach balls, build a killer playlist, and direct your GPS to the corner of nature and beauty for a seasonal escape to some of the mighty Midwest’s most idyllic towns. Wisconsin’s Lake Geneva, with its wide open shoreline, panoramic vistas, and friendly downtown makes for an excellent sojourn while verdant hill-scapes from Otsego, Michigan to Illinois’ own picturesque Galena cater to mountain bikers yearning to burn trail. Got a little extra cash on your hands? Go ahead and treat yourself to a top notch stay in one of these swanky Airbnbs.

Pitch a blanket for a dreamy outdoor picnic

After a year stuck at home, we’d wager that your cooking skills have never been sharper—I mean, as we pointed out over the winter, a slew of culinary giants no less lofty than two-time James Beard winner Paul Kahan were offering up interactive classes. If you’re proud of any newfangled cheffing skills, now’s the time to flex them by packing up a professional-grade picnic. When it’s time to unwrap the romance, our beautiful city has got you covered—literally. The Chicago Park District encompasses 570 parks spread out across some 7,600 acres. Did someone say, charcuterie?

Zip, climb, and dine at The Forge: Lemont Quarries

Everyone’s favorite humongous ropes course, zipline park, and otherwise outdoor thrill bonanza is kicking things up a notch this summer with their brand new Zip, Climb & Dine package. Adventurous paramores are invited to scale one of the country’s tallest ropes course towers to enjoy a romantic meal amid the clouds while marveling at the sparkling Chicago skyline in the distance. And you know what comes next—an after-dinner zipline descent, of course, one that will have you soaring over the gaping quarry while your supper settles peacefully in your stomach (fingers crossed).

Cuddle up at a drive-in movie 

Still not entirely comfortable with indoor crowds just yet? That’s completely reasonable after all you’ve been through. And thankfully there’s no shortage of al fresco options to keep you safe and entertained. Cruise over to ChiTown Movies in Pilsen for some good old-fashioned front seat fun set to the tune of modern classics like Mean Girls, Dirty Dancing, Scream, and more. And remember to come hungry—resident snackbar ChiTown Grille is standing by to deliver a full bill of tasty treats right to your driver’s side door. 

Got more of a ‘Netflix and chill’ vibe going on? Well, you’ll be stoked to learn that plenty of award-winning cocktail joints are continuing to box up their boozy splendors just for you. We’re talking big names like the AviaryViolet HourThree Dots and a Dash, and more, all exquisitely prepared and portioned for at-home consumption. Handlebar mustaches and leather suspenders sold separately.  

Embark on a DIY brewery crawl

With so many great craft breweries clustered around the city, organizing a bicycle- or foot-powered suds crawl for two is always a failsafe date idea. What’s more, plenty of taprooms have expanded into beer gardens and other sidewalk accommodations for sharing open-air pints. It’s all about the ambience! Just pick a neighborhood (pro tip: Milwaukee Avenue from the Near Westside to Logan Square is a fantastic place to start), strap on a mask, and hit the streets in search of sweet (or sour, or roasty, or bitter) Chicago-brewed suds.

Level up with a sky-high curling session

Take your dating game to new heights by throwing in a little friendly competition alongside the cocktails. WhirleyBall, you say? Please… That’s so pre-pandemic. The COVID era is curling’s time to shine. Yes, that curling. Throughout winter it cropped up as the bar game du jour at drinking dens all over the city, with newcomers sliding across the ice at Kaiser TigerWhiskey BusinessHarvest at Lakeshore Sport & Fitness, and Upstairs at the Gwen. But even in the absence of winter weather, the competition is still scorching hot at the Chicago Curling Club. So book a lane—or whatever curlers call them—and prepare to sweep your beloved off their feet (sorry, not sorry).

Cool down with a cold one at a rooftop or patio bar

Drinking outdoors has never been hotter (get it?). Make the most of it with some swanky open-air sipping at dependable destinations such as Lincoln Park’s towering J. Parker, Wicker Park newcomer Kennedy, loungey River North hot spots I|O Godfrey and Joy District, and South Side haunt the Woodlawn. Hotels are also a frequent setting for al fresco winners, including Raised on the third floor of the Renaissance and the stunning new Rooftop at Nobu Hotel. Just remember, you don’t have to stay there to play there (though it might be more fun it you do… ).

Want more Thrillist? Follow us on Instagram, Twitter, Pinterest, YouTube, TikTok, and Snapchat.

Meredith Heil is a contributor for Thrillist. 
Brad Japhe is a contributor for Thrillist.
Our Newsletter
Become a Local Insider in Chicago
Get our expert guides to your new favorite city.
By Signing Up, I Agree to the Terms and Privacy Policy.