Chicago’s 12 Coolest and Most Romantic Summer Date Ideas
These dates are sure to impress and will make any outing with your significant other feel special.
The sun is shining, the temperature is rising, and Lake Michigan is almost fully thawed out, which can only mean that summer has officially arrived in Chicago. There’s no better time to throw on your favorite crop top and shorts, text your partner, and whisk them away for a wonderful day on the town before the city we call home freezes over again in mid-September. And for fun things to do with anybody in your crew, check out our equally compelling list of platonic seasonal activities.
Step into the squared circle with some pro wrestling action
There are few things more romantic than watching somebody throw somebody else through a table. Luckily, Chicago is home to a variety of independent wrestling promotions that put on shows all over the city. Big-name AEW, WWE, Impact, and NJPW talent like Zack Sabre Jr., Keith Lee, Athena, Will Ospreay, Kylie Rae, Thunder Rosa, and many others have stopped in to wrestle in the windy city—these shows are not to be missed. Visit Freelance Wrestling, AAW, and Warrior Wrestling’s official websites to keep track of upcoming events and get tickets. Then, get your beau a frosty beer and settle in for a date night that neither of you will ever forget.
Embrace the cringe and become a tourist again
When was the last time you and your partner got dolled up and explored downtown? As hokey as it may sound, summer is the perfect time to remind yourself that the touristy stuff is touristy for a reason. There are few things more romantic than strolling through a museum holding someone’s hand, so don’t miss the Museum of Science and Industry’s LEGO exhibit boasting the largest-ever collection of LEGO art (open through September 5), and the Chicago Art Institute’s a Cezanne exhibit (also open through September 5). That said, our top pick for a cringy-touristy-but-worth-it Chicago summer date, assuming you haven’t done it recently, is to head down to the river and book an architectural boat tour. The beauty of the riverside buildings will provide a wonderful backdrop for the beauty of your partner.
Fine-tune your beach bods with the city’s best workouts
It’s been 100 degrees for the past week. We’re all sweaty. No need to be shy about it, so why not sweat it out together courtesy of one of the city’s go-to workouts? For ambitious types (who aren’t afraid to get competitive with their cutie), opt for a class at SoulCycle, where 45 minutes of synchronized bike movements can give you a solid perspective on whether or not your honey can cut it on the dance floor. With numerous rides per day at locations throughout the city (and one in Skokie), you’ve got plenty of options for how and when you pedal with your plus one. If you’re in a Sunday-kind-of-love mode, keep it chill with a class at Zen Yoga Garage, where expert instructors guide students through breath-to-movement classes that are as grounding as they are groovy.
Celebrate the comeback of the Green City Market
Once you’ve won over your number one with your cooking skills, it’s time to show them where you scored those ace ingredients. The Green City Market has returned for the summer, bringing with it 58 local farmers and producers including several new vendors by way of Flatwater Farms from Buchanan, Michigan and Kankakee Valley Homestead from Walkerton, Indiana. Expect longstanding market favorites, too (such as Nichols Farm & Orchard and Mick Klug Farm), along with a few exciting new food vendors—case in point with Molino Tortilleria, an heirloom corn tortilla purveyor sourcing corn from local farmers, and Flat & Point, a Logan Square mainstay featuring sourdough, bagels, and other baked goods. Check out the upcoming dates here.
Marvel at Chicago’s most breathtaking blooms
Flowers on a date are always a good idea—especially if you’re discovering them together. It’s a feat made all the easier in the summer, with the warm breeze stirring up floral scents across the city. Garfield Park Conservatory and Lincoln Park Conservatory showcase sweeping landscapes of color, but our summer date pick is the Chicago Botanic Garden. It’s their 50th anniversary, and they’re running constant events featuring art installation, live performances, and much more.
There are now myriad sites across Chicagoland offering COVID-19 vaccines and boosters—so why not make a weekend of it? We’re just saying. Could be cute. And if your honey happens to faint at the sight of the needle, at least you’ll be there to catch them.
Size up each other’s dance moves at a concert
Live music is making a fierce comeback at all of our favorite local venues—and things are only heating up this summer. Of course, if you really want to impress your date, you’ll surprise them with a VIP pass to Lollapalooza, but if that’s a bit out of your price range, buy your beau tickets to one of the many official aftershows, featuring acts like 100 gecs, The Wombats, Tove Lo, DUCKWRTH, and Caroline Polachek. Also, don’t allow Lolla to overshadow Pitchfork Music Festival and Riot Fest. Looking for something slightly more under the radar? Schubas and Beat Kitchen are both legendary venues where you’ll be able to get a glimpse of bands before they start playing arenas. LA’s Cheekface is playing Beat Kitchen on July 23, and psych-indie-rock foursome Meltt is playing Schubas on August 7. And if classical or jazz is more your frequency, book it to one of Fever’s Candlelit Concerts, which span everything from Mozart to Miles Davis tributes.
Splurge on a luxury staycation
When a full-on excursion feels too costly—or like too much of a commitment—nothing sets the mood like a properly staged staycation. After a recently completed multi-million-dollar renovation, the Four Seasons Hotel Chicago reopened its doors with brand-new public spaces featuring open floor plans, textured jewel tones, and thoughtful art curation (including an eye-catching installation by Toronto-based Unitfive Design, an abstract interpretation of a tree canopy meant to honor Chicago’s closeness to nature). Check into one of the 374 rooms, then head straight to Adorn, where James Beard-award winning chef Jonathon Sawyer serves globally inspired cuisine showcasing the Midwest’s bounty (the majority of which is sourced within 200 miles of the restaurant). Enjoy plates like Duck Confit Pappardelle or Pan-seared Ora King Salmon, and save room for dessert: Pastry chef Juan Gutierrez (recent winner of Netflix’s School of Chocolate) has several of them up his sleeve, including the PB & Jam It (with peanut mousse, roasted grape sorbet, and toasted bread ice cream) and the Pistacia Vera (with semolina cake, pistachio ice cream, and kataifi). Come morning, check out Sunday brunch, where you can pair your fare with live music.
Chicago’s dining scene continues to dazzle, and dishes go down so much easily in the company of your love. Lure Fishbar puts up impressive plates of sushi and seafood on the Mag Mile, while the South Loop continues to draw savvy city dwellers to Mercat a la Planxa, The Exchange, The X Pot, and Apolonia. And for those seeking a little escape, flee the city (if only via your palates) with visits to Tzuco for elevated Mexican fare or Bocadillo Market for Spanish-inflected sandwiches and shareables.
Keep the good eats a comin’ with stops at TriBecca’s Sandwich Shop for chef Becca Grothe’s epic take on the almighty Cubano, or head to Goddess and Grocer West Loop, the latest (and largest) outpost from the beloved deli, sandwich shop, and bakery that continues to peddle favorites from local vendors (think Inbictus Factory, Hewn, Mera Bites, and Victory Dance Foods). At Mortar and Pestle, chef Stephen Ross serves up thoughtful, international-leaning morning fare, while at Kasama, Genie Kwon and Timothy Flores excel at Filipino-focused cuisine and innovative baked goods by way of options like Fried Pork Spring Rolls and truly game-changing Longanisa, Egg, and Cheese Breakfast Sandwiches.
Savor the summer on a weekend getaway
Have wheels, will travel. Pack your s’mores kits, build an epic indie playlist, and direct your GPS to the corner of nature and beauty for a seasonal jaunt to some of the mighty Midwest’s most charming escapes. Madison, with its lakeside vistas and dynamite dining proves to be an excellent destination this time of year. The scene is just as bustling in Iowa City, home to dozens of cozy cafes and restaurants worth their salt (including Pullman Bar & Diner, The Dandy Lion, and The Webster). And over in Kohler, the illustrious American Club (and all of its A-grade amenities, from a world-class spa to ultra-romantic private cabins) continues to impress throughout the year. Got a little extra cash on your hands? Go ahead and treat yourself to a top-notch stay in one of these luxurious Airbnbs.