Stay Warm in Chicago All Year Long with These Hot Date Ideas
From ‘90s-themed escape rooms to luxurious staycations, there’s plenty of romance in Chicago.
Chicago may be cold nine months out of the year, but that doesn’t mean we can’t help you heat things up. We’ve curated a local selection of hot date ideas, from indoor haunts to outdoor adventures. Whether you and your beau want to scale new heights rock climbing, level up at one of the area’s many arcades, or simply walk hand-in-hand outside among the most beautiful foliage Chicago has to offer, we’ve got you covered no matter what the vibe is.
Food and Drink Date Ideas in Chicago
At the unsurpassed Kasama, Genie Kwon and Timothy Flores offer Filipino cuisine and innovative baked goods by way of options like fried pork spring rolls and truly game-changing longanisa, egg, and cheese breakfast sandwiches—but the best part is that it’s all ready to take on the go. Whisk your beau there, and then take your deliciousness as you stroll through Ukranian Village or Wicker Park.
North Center’s premier French restaurant is a date-night must, and not just for its incredible food (don’t skip the Pain Et Beurre, steaming hot bread with garlic confit and a seasonal compound butter). The larger-than-it-seems patio is so incredibly cozy and intimate that you’ll feel transported to the cobblestone streets of Saint-Tropez. Go for an early dinner and watch the sunset.
Once you’ve won over your number one with your cooking skills, show them where to score those ace ingredients. Green City Market has multiple locations around the city, featuring 58 local farmers and producers, including several new vendors by way of Flatwater Farms (Buchanan, Michigan) and Kankakee Valley Homestead (Walkerton, Indiana). New food vendors include 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. Meanwhile, longstanding market favorites like Nichols Farm & Orchard and Mick Klug Farm will be there as well. Check out the upcoming dates on the Green City Market website. As a bonus, during the winter months, the market’s indoor Avondale location stays open.
Over the past few years, advances in outdoor seating and heating solutions have made it possible for Chicago’s best rooftop bars and restaurants to keep couples comfy all year round, even on those odd days in May when it’s randomly 37 degrees out. If you’re looking for a romantic rooftop getaway, braving the crowds at Navy Pier—wait, hold on, we promise it’s worth it—to take in Offshore Rooftop’s food, drink, and views. It’s the world’s largest rooftop bar, meaning there’s actually likely to be seating available for you and your date.
When a full-on excursion feels too costly—or like too much of a commitment—nothing sets the mood like a properly planned staycation. After a recent multi-million-dollar renovation, the Four Seasons Hotel Chicago reopened its doors with new public spaces featuring open floor plans, textured jewel tones, and thoughtfully selected art (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 Diver Scallops (with crispy guanciale) or Short Rib Pappardelle, and consider popping in on Saturday night or on Sunday for brunch, when you can pair your fare with live music and DJ performances, courtesy of Adorn’s collaboration with BELLOSOUND.
Cultural Date Ideas in Chicago
Strolling through a museum holding someone’s hand means romance. Interactive exhibits feed a romantic spark best, and the Museum of Science and Industry is perfect. Not only is it a beautiful building, situated in a picturesque pocket of Hyde Park, but the exhibits are consistently top-notch. Be sure to say hi to the baby chicks.
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. Freelance Wrestling regularly hosts legendary talent like Mick Foley, Keith Lee, Athena, Will Ospreay, Kylie Rae, Thunder Rosa, and many others to their windy city events, which they host on a regular basis. Coming up this spring, Chicago’s own former WWE superstar Mustafa Ali is returning to the city to wrestle with the promotion, so keep your eye on the Freelance Wrestling event page because tickets, although they are affordable, will sell out. Buy some merch, get your beau a drink and settle in for a date night that neither of you will ever forget.
For couples that relish in a bit of puzzle-solving, Quandary Escape Rooms has it covered. Grab your significant other and maybe another couple or two for an escape room triple date. Steps from the Belmont brown/red line station, Quandary features a wonderfully retro “Escape the ‘90s Room” full of nostalgic touches, including custom-modded Super Nintendo games. That said, it’s probably a good idea to wait on the escape room date until you’ve been together for a little bit, especially if you or your partner get frustrated easily.
Sports and Gaming Date Ideas in Chicago
There’s no better way to build trust than to have climbed 50 feet, muscles aching, and then look down and see your significant other give you the thumbs up, letting you know that they’ve got you, that you’re doing great, and that they will literally catch you if you fall. Climbing might not be a traditional date-night activity, but trust us and check out one of First Ascent’s guided climbing sessions.
Many of us know The Ribbon as a primo winter date spot, a perfect place to ice skate hand in hand with your beau while taking in breathtaking views of the city before retiring for a hot cocoa. But the park is open year-round, and when the ice skating season is over, The Ribbon opens up for climbing, bungee, roller blading, and scooter-ing. The rest of Maggie Daley Park deserves mention too, featuring mini golf, tennis, picnic groves, and plenty of other perfect date activities. Trust us, it’s worth the trip downtown.
Although busy weekend nights mean that many of Chicago’s arcade bars fall short of ideal date night spots, not much can compare to making the trek up north to North Riverside, having a couple of drinks, facing off over an intense round of Dance Dance Revolution, and then grabbing a bite to eat. For extra credit, visit the arcade’s gigantic section of Japanese-style crane machines and win your beau a plushy or toy that you probably could have bought on Amazon for less than you spent trying to win it. It’s the journey, not the destination.
Health and Wellness Date Ideas in Chicago
If you’re looking for a date that feels like a staycation packed into a few hours, look no further than AIRE Ancient Baths. From the moment you step into the River North warehouse it calls home, you’ll be transported into a luxe spa and bathhouse experience, featuring a variety of baths of different temperatures, salinities, and styles, from a steamy hot caldarium to the 50 degree frigidarium, to a special indoor-outdoor pool, to a high-salinity floating pool, to a “pool of a thousand jets” that absolutely lives up to its name. Multiple date-ready experiences are available, from aromatherapy to romantic couples’ massages and beyond. For Valentine’s Day, they’re hosting a special Velvet Garden event where couples can indulge in a bathing experience complete with romantic florals, aromatherapy, and macarons.
Flowers on a date are always a good idea—especially if you’re discovering them together. Absolutely make a point of taking advantage of the blooms, assuming the weather permits it. Be sure to visit the colorful Circle Garden, as well as the Lakeside Gardens—if you visit in late April or early May, you’ll be treated to 300 blooming crabapple trees by the glittering basin. It’s the perfect spot for a romantic stroll hand-in-hand with your soulmate.
It’s easy to fall into a bit of a Netflix-and-chill rut (no shade though) when fickle Chicago weather turns rainy and cold. There are few things cozier than cuddling on the couch with a cup of tea when it’s storming out. But sometimes, it’s helpful to remember that there’s a world outside your fuzzy blanket, and getting a sweat in with a loved one can really help connect you both to the world around you, and each other. Zen Yoga Garage offers a variety of different classes from Flow to Burn to Vinyasa, complete with expert trainers to help you through your workout no matter your ability.