Fun Things to Do in Chicago for Couples
Chicago is famous for its hot dogs, sports teams, deep-dish pizza, and vibrant culture—but let’s not overlook its romantic charm. While the Windy City might not top the charts as a romance capital, it’s brimming with opportunities for couples to connect and create unforgettable memories. In this blog post, I’ll share some fantastic date ideas that will not only showcase the city's unique charm but also help you and your partner fall even more in love with everything Chicago has to offer - and each other.
For the Artsy Couple
Chicago is the perfect place to be a lover of the arts. Here are some ideas to enjoy with your muse:
Explore The Art Institute (Duh)
Take a trip to one of the nation’s most iconic art museums! Get dressed up, have lunch (The Gage is a crowd favorite) and enjoy masterpieces from around the world. Bonus points if you can make up a game to play with one another while you’re there, like I Spy!
Catch a Shakespearean Performance
For the theater kids at heart, the Lion theater on Navy Pier showcases incredible adaptations of Shakespeare and other theatrical gems. Drunk Shakespeare is also a must see to combine the classics with some raunchy comedy. Hey-ho!
Browse a Gallery Night in River North
Explore the River North Gallery District during one of its open gallery events. Sip wine and enjoy conversations with local artists while discovering up-and-coming talent.
Create in a Ceramics or Painting Class Together
Sign up for a hands-on experience at places like Lillstreet Art Center, where you can create your own pottery or paintings and take home a tangible memory of your date. For those who don’t want to get their hands that dirty, Glazed Expressions in Lincoln Park offers awesome BYOB pottery painting sessions with plenty of pre-fired ceramics to choose from.
Explore the Chicago Cultural Center
This hidden gem is not only architecturally stunning but also features free art exhibits, performances, and events year-round. It's a low-pressure way to soak up some culture.
Go on an Architectural Boat Tour
Architecture is art, too! Take a boat tour to learn about the city’s iconic buildings and the stories behind their designs—a perfect date for architecture enthusiasts.
For the Foodies
To keep this blog post concise, I’ve focused on date ideas that go beyond simply dining at my favorite restaurants. Here are some ideas where food and creativity come together:
Take a Cooking Class Together
Yes, chef! From pasta-making at Eataly to sushi-rolling workshops, Chicago offers plenty of hands-on culinary classes where you can learn new skills while enjoying delicious food. Pick a cuisine you’d love to be able to remake at home, and make sure you take notes as you go!
Enjoy the View at a Rooftop Restaurant
If you’re not afraid of heights, enjoy a romantic dinner with skyline views at spots like Cindy’s Rooftop or LH Rooftop. Great food paired with an interesting atmosphere makes for an unforgettable evening.
Shop and Snack at the Chicago French Market
Wander through this indoor market, sampling everything from crêpes to macarons, and pick up gourmet ingredients (especially wine!) to create your own meal at home. Parking is free for one hour!
Get Fancy (Or Not) with a Michelin-Starred Meal
Get fancy and celebrate a special occasion with a reservation at one of Chicago’s renowned Michelin-starred restaurants like Alinea, Oriole, or Smyth for an extraordinary dining experience. Or, try recreating one of their menu items based on description at home.
Sip and Savor at a Wine or Beer Pairing Dinner
Attend a pairing event at a local spot like City Winery or Revolution Brewing, where expert pairings enhance the flavors of each dish and drink.
Go Have a Picnic at Millennium Park
Grab your favorite snacks from a nearby market like Mariano’s or Eataly and enjoy a feast of your liking while soaking in the beauty of Millennium Park.
For the Kids at Heart
If you’ve been healing your inner child one hobby at a time, these are the dates for you. Chicago offers countless opportunities to let loose and embrace the carefree wonder of the city.
Explore the Waters at the Shedd Aquarium
The Shedd Aquarium is a great place to wander around with your partner, marveling at dolphins, penguins, and jellyfish. Grab some popcorn, laugh at the weird looking fish, and enjoy being a kid again. Just… try not to tap the glass.
Horse Around at the Brookfield Zoo
A day at the zoo is sure to incite memories of childhood. Go in the summer for a sunny stroll, or in the winter to ogle at the zoo lights. Either way, the animals will be happy to see you!
Skating at Maggie Daley Park
Another activity you can enjoy in various seasons! Hop on roller skates (or ice skates) and glide around the skating ribbon at Maggie Daley Park. If you’re not practiced, embrace the falls and the giggles that accompany them!
On the Boardwalk… Having Some Fun
The Navy Pier is Chicago’s closest thing to a boardwalk. Head there for a ride on the Centennial Wheel, a high speed boat ride on their Seadog Boat Tours, or a scoop of ice cream at the Rainbow Cone stand. It’s like being at the Jersey Shore, but not!
Learn Something New at the Museum of Science and Industry
Engage with hands-on exhibits like the Science Storms, the mirrored maze, or the space exhibits. It’s an interactive experience that’ll make you feel like curious kids all over again.
Roll a Turkey at Lucky Strike
Embrace your inner athlete while enjoying music, snacks, and drinks in a lively, retro-inspired atmosphere. This fun, competitive date can bring out your inner child, (especially if you need the bumpers).
For the Chillers
If you’re typically cozied up on the couch together, consider venturing out to take advantage of some of Chicago’s most peaceful and low-key activities.
Watch the Sunset at Oak Street Beach
Pack a blanket, grab a few snacks, and head to Oak Street Beach for a serene sunset view over Lake Michigan.
Take a Quiet Moment at Lincoln Park Conservatory
Take a leisurely stroll through the lush gardens and tropical greenery at the Lincoln Park Conservatory. It’s a tranquil escape from the hustle and bustle, perfect for couples who appreciate nature (and peace and quiet).
Cozy Up at a Local Coffee Shop
Find a cozy neighborhood café, like Intelligentsia or The Wormhole Coffee, and enjoy a relaxing afternoon sipping coffee and chatting in a comfortable, laid-back setting. Bring cards or a board game to really amplify your time together.
Enjoy Dinner and a Movie at the Alamo
For a chill, comfortable date night, catch a film at the Alamo Theatre. Come hungry and enjoy the 5 star service straight to your seat. No more getting up halfway through to get a refill! Come 30 minutes early to catch a special before-show reel of clips from related media.
Take a Chill Bike Ride Along the Lakefront Trail
Rent bikes and take a leisurely ride along the Lakefront Trail. Stop for a break by the lake, enjoy the views, or just cruise at a relaxed pace.
Unwind at a Low-Key Jazz Show
Spend an evening at the Green Mill Cocktail Lounge, where you can enjoy live jazz in a dimly lit, intimate space. The chill ambiance and smooth tunes create the perfect date for relaxing and enjoying each other’s company.
For the Wellness Seekers
Chicago is an activity mecca. Nourish your mind, body, and soul with some of these activities sure to make you feel good.
Be One with the Earth at an Outdoor Yoga Class
Something about being outside while doing yoga really grounds me and makes me feel one with the world. If you read that sentence and didn’t cringe, you’ll love this city’s selection of outdoor yoga classes hosted when the weather gets nice. Check out Yoga Now Chicago to find a class in your area!
Graze on a Plant-Based Dinner at Chicago Diner
Enjoy a healthy, plant-based meal at the Chicago Diner, one of the city’s most beloved vegetarian restaurants. It’s a great option for those who want to nourish their bodies with wholesome, delicious food.
Heal at a Sound Bath at The Centered Mind
Experience a calming sound bath at The Centered Mind, where healing vibrations from crystal bowls and gongs help relax your nervous system. It’s a serene way to let go of stress and find peace together.
Try Out a Paddleboarding Class on Lake Michigan
Try something new and adventurous by taking a paddleboarding class together on Lake Michigan. It’s a great way to enjoy physical activity while bonding with nature and each other.
Learn at a Wellness Workshop or Retreat
Look for local wellness workshops or retreats focusing on holistic health, mindfulness, or fitness. Whether it’s a one-day retreat or a weekend getaway, it’s a great way to deepen your connection and nourish both your bodies and minds. Eventbrite is a great place to explore your options for events that suit both of your interests.
Fly at AcroYoga Together
For a totally unique and fun wellness experience, try AcroYoga at Acro Chicago. It’s a playful yet relaxing activity that involves partnering up for yoga poses and stretches, combining trust, balance, and laughter.
Conclusion
Of course, this list is not an exhaustive one; take inspiration, follow suit, or nix the list and come up with your own Chicago activity. Whatever you choose, Chicago is the perfect place to be bored. There is a nonstop influx of new activities, events, and opportunities to connect in the Windy City.