The Most Romantic Things to Do on a Couples Trip to Chicago
From low-key to over-the-top, these are the most fun and romantic things for couples to do 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. Whether you’re local or traveling to the city with your partner, we’ve curated a local selection of local activities for couples looking for a cute place to eat, a spot to face off in your favorite arcade games, or trying to savor the romantic tension inherent in a stressful escape room. Maybe you two 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—no matter what, the Windy City has something both of you will enjoy.
If you like competition
North Riverside, Prices vary
Although busy weekend nights mean that many of Chicago’s arcade bars fall short of ideal couples’ hangouts, 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. Visit the arcade’s gigantic section of Japanese-style crane machines and win your significant other a plushy or toy that you probably could have bought on Amazon for less than you spent trying to win it. Remember, it’s the journey, not the destination.
Multiple locations, Prices vary
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. Our favorite is Freelance Wrestling, which 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. Local legend Isaias Velasquez just wrestled AEW star Danhausen at a sold-out show, so keep your eye on the Freelance Wrestling event page because tickets, although they are affordable, will sell out. Buy some merch, get a drink, and settle in for a night that neither of you will ever forget.
Lakeview, $35 per person
For couples that relish in a bit of puzzle-solving, Quandary Escape Rooms has it covered. Maybe even invite another couple or two for an escape room triple date. Steps from the Belmont brown/red line L 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.
If you like to stay active
Multiple Locations, $29 per person for bouldering classes, $49 for top rope
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 romantic couples’ activity, but trust us and check out one of First Ascent’s guided climbing sessions, it’s worth it even if you’re only in town for a few days.
Bucktown, $30 for a drop-in class
It’s no secret that some (okay, most) of Chicago’s best attractions involve eating and drinking copious amounts of delicious things. If you’re feeling a bit gross after a carb-heavy Chicago weekend, getting a sweat in with a loved one can really help refresh you. 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.
Millennium Park, Prices vary
Chicago locals know The Ribbon as a primo winter date spot, a perfect place to ice skate hand in hand 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, rollerblading, 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.
If you’re looking for classic romance
River North, prices vary
If you’re looking for a truly luxe Chicago experience compressed 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 truly singular 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.
North Center, prices vary
There are plenty of romantic spots in the city, and every local has their own favorite. Here’s where your humble writer will share his own with you. Whether you’re local or traveling to the city I call home, do yourself (and your beau) a favor and stop by the North Center neighborhood’s premier French restaurant. Of course, they serve incredible food (don’t skip the Pain Et Beurre, steaming hot bread with garlic confit and a seasonal compound butter), but the real draw is the scenery. 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, experience the sunset, and as the outdoor lights turn on, reveal the bouquet of flowers you’ve brought along as a “just-because” gesture.
Glencoe, Admission is $22 for locals, $24 for visitors from outside the county
Flowers on a date are always a good idea—especially if you’re discovering them together. Lovebirds should absolutely make a point of venturing outside the city a little bit to take advantage of the blooms. 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.
Ukrainian Village
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 with you as you stroll through scenic Ukranian Village or Wicker Park.
Magnificent Mile
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). Of course, we recommend it if you’re looking for a place to stay (or staycation) in Chicago, but even if you’re not spending the night at the hotel, there’s still plenty to enjoy. 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 ham hock consomme) or Short Rib Gnocchi, 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.
If you’re looking for something touristy
Hyde Park, $17 for locals, $26 for out-of-county visitors
Strolling through a museum holding someone’s hand means romance. Interactive exhibits feed a romantic spark best, and as locals will tell you, the Griffin 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.
Multiple Locations, prices vary
Whether you’re a local looking to impress with where you score your ace cooking ingredients or a tourist looking for a tasty souvenir to remember your romantic Chicago trip by, Green City Market is a must. The 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.
Navy Pier
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.