Swipe Right on These 23 Date-Worthy Things to Do in Chicago for Couples
Too many date nights end with scrolling through your phone and ordering takeout. Again. Chicago has way too many incredible experiences to let your weekend plans go to waste like that.
Whether it’s skyline views from 1,000 feet up or jazz clubs with dim lighting and even dimmer cocktails, the city practically invented the vibe shift.
There’s a whole lineup of romantic things to do in Chicago that aren’t just romantic; they’re actually fun!
From architecture cruises and candlelit fondue to riverside strolls and speakeasy magic shows, these are the things to do in Chicago for couples that’ll make your next date feel like a main character moment.
So go ahead, ditch the decision fatigue and pick something that makes you both say “Let’s go!”
Cute Places to Eat, Sip, and Stare Into Each Other’s Eyes
Geja’s Cafe
Slip into one of the most hidden romantic spots in Chicago, where candlelight, fondue pots, and live classical guitar set the mood without trying too hard.
The space feels intentionally tucked away, like a secret you only share with someone worth impressing.
Dinner here is slow, cozy, and refreshingly disconnected from the outside world. Geja’s Cafe turns a simple meal into a full-on “remember this forever” kind of night.
Bavette’s Bar & Boeuf
For a classic date night that feels equal parts indulgent and intimate, Bavette’s Bar & Boeuf absolutely delivers.
Dim lighting, leather booths, and perfectly paced service make it feel like time slows down the second you sit.
It’s the kind of place where conversation flows easily and ordering dessert feels non-negotiable. Bavette’s Bar & Boeuf is ideal for nights when staying in just doesn’t cut it.
Green Mill Jazz Club
If live music and old-school charm are your thing, this is one of the most unforgettable romantic things to do Chicago has to offer. The Green Mill Jazz Club wraps you in vintage vibes, smooth jazz, and a little bit of mystery.
The low lighting and soulful sounds make it easy to lean closer and linger longer. It’s effortlessly cool without feeling performative, which is exactly the appeal.
Rooftop Bars
Chicago’s Windy City reputation hits differently when you’re sipping cocktails high above the skyline. Rooftop bars like Cindy’s Rooftop or LondonHouse Chicago Rooftop turn casual drinks into a full sensory experience with sweeping views and golden-hour lighting.
Whether it’s skyline selfies or quiet moments watching the lights flicker on, the setting does most of the work. Rooftop bars are perfect for dates that start casual and accidentally become memorable.
Chicago Premier Dinner Cruise on Lake Michigan
Nothing sets the tone quite like cruising across Lake Michigan with the city glowing behind you. The Chicago Premier Dinner Cruise feels cinematic, combining skyline views with a calm, elegant atmosphere.
Every angle offers something worth staring at, whether it’s the water, the lights, or your date across the table. It’s a standout choice for couples who want their night to feel a little elevated.
Spirit of Chicago Lunch Cruise
For a relaxed daytime option near Navy Pier, this cruise turns lunch into a scenic escape. The Spirit of Chicago Lunch Cruise offers fresh perspectives of the city without the pressure of a formal evening out.
Sunlight, skyline views, and unhurried conversation make it feel easy and enjoyable. It’s proof that romance doesn’t have to wait until after dark.
Stuff That’ll Make You Say, “Wait, We Can Do That Here?”
AIRE Ancient Baths
If your ideal weekend getaway includes dim lighting, warm pools, and zero phone notifications, AIRE Ancient Baths is the vibe. Set in a restored industrial building, this romantic hideaway invites you to float, soak, and reconnect in total tranquility.
With candlelit chambers, thermal baths, and optional massages, it’s basically a love language in spa form. For couples craving a slow, sensory reset—this is the spot.
Chicago River Architecture Tour
Looking for a date that blends sightseeing with storytelling? This award-winning architecture tour is surprisingly romantic—especially when the sun sets, and the skyline starts to glow.
You’ll cruise down the Chicago River while learning the stories behind the city’s most iconic buildings. It’s equal parts educational and eye-candy, and yes, very couple-approved.
Cooking or Pottery Classes
Getting your hands dirty together is underrated, and these couple activities Chicago serves up are way more fun than watching Netflix in silence. Whether you’re spinning clay at Penguin Foot Pottery or sautéing pasta at The Chopping Block, there’s something special about creating side by side.
These low-pressure, high-reward date ideas are great for laughter, learning, and maybe a little healthy competition. Bonus: you might walk away with a new skill and a cute shared memory.
Chicago Magic Lounge
Tucked behind a laundry facade and filled with wonder, the Chicago Magic Lounge is one of the most romantic things to do in Chicago for couples who love a little surprise with their date night.
Think cocktails, velvet chairs, and up-close illusions that leave you whispering “how did they do that?”
It’s immersive, unexpected, and way more intimate than a crowded comedy club. For couples who’ve “done it all,” this place proves you haven’t.
Flyover Chicago
Soar above the skyline without ever leaving Navy Pier! Flyover Chicago is a high-tech thrill ride that offers the same butterflies as an observation deck, but with a lot more movement and mist.
This immersive experience wraps you in sound, visuals, and even scents as you fly over Chicago’s most iconic landmarks. It’s short, sweet, and just the right amount of wow for adventurous duos.
Medieval Times Dinner and Tournament Illinois
If sharing a massive feast with your hands while cheering on knights sounds like your love language, you’ll love this one.
Food tours are as great as trying the famed deep dish pizza, but this experience kicks it up a few jousts.
It’s playful, dramatic, and low-key hilarious—and somehow, still very romantic. Medieval Times is the kind of date you’ll both still be talking about next weekend.
Chicago Theatre Tour Experience
Step backstage at one of the city’s most iconic landmarks with the Chicago Theatre Tour, where grandeur meets history in the best way.
Perfect for lovers of drama (the fun kind), this one leans into all things Chicago cultural.
You’ll learn fun facts, walk storied halls, and maybe even share a quiet moment center stage. It’s a behind-the-scenes look that feels extra special when shared.
Medieval Torture Museum Chicago
Looking for something completely offbeat and unforgettable? This one’s weird, dark, and surprisingly bonding—because nothing says romance like shrieking in disbelief together.
Medieval Torture Museum Chicago earns its spot for your list of things to do in Chicago for couples for novelty alone. It’s definitely for those who like their date nights a little twisted (in the best way).
American Writers Museum
Quieter but no less compelling, the American Writers Museum is ideal for couples who love language, literature, and a little lingering between exhibits.
Interactive and beautifully designed, it’s more fun than you’d expect a museum about words to be.
Located near Millennium Park, it’s a smart stop during a romantic downtown wander. If words are your love language, this one’s a must.
Touristy Windy City Staples That Still Give Us Butterflies
The Centennial Wheel & Navy Pier
If your love story needs a skyline view, the boat tour at Navy Pier plus a spin on the Centennial Wheel is as classic as it gets.
Whether you’re gliding across Lake Michigan or sharing a gondola with views of the city lights, this combo screams romance.
It’s fun, flirty, and just the right kind of touristy. Plus, holding hands 200 feet in the air? Absolutely a core memory.
Art Institute of Chicago
Home to works like American Gothic and Nighthawks, the Art Institute of Chicago is an ideal stop for couples who swoon over culture.
Wandering the quiet halls, sharing commentary (or just pretending to get modern art) feels intimate and inspiring.
It’s romantic in that cerebral, “we’re growing together” kind of way. Plus, café dates after museums always hit different.
Shedd Aquarium
Dive into date day with a trip to the Shedd Aquarium, one of Chicago’s most beloved and immersive experiences.
Between the playful otters and the jellyfish tunnels, you’ll find yourselves wide-eyed and maybe a little more in love.
It’s interactive, it’s adorable, and it gives you something to talk about besides where to eat next. Bonus: low lighting and ocean vibes make this a surprisingly cozy indoor date.
Outdoor Strolls & Gardens
From the scenic Chicago Riverwalk to the breezy Lakefront Trail, this city was made for strolling with your favorite person.
Add in the lush beauty of Garfield Park Conservatory and the blooming pathways of Chicago Botanic Garden, and you’ve got the perfect mix of nature and city.
These are go-to spots for real connection—no distractions, no pressure. Just miles of views, fresh air, and each other.
Skydeck Chicago
On the 103rd floor of Willis Tower, the Skydeck Chicago takes your relationship to new heights—literally. Step onto The Ledge, a glass balcony over a thousand feet above the streets, and try not to gasp.
It’s adrenaline-packed but also a shared experience you’ll always remember. Bonus points if you take a kissing selfie with the skyline as your backdrop.
Big Bus Tours Chicago
Hop on, cuddle up, and let someone else do the navigating. Romantic things to do Chicago don’t always mean candlelight—sometimes it’s just easy sightseeing and laughs from the top deck.
This hop-on-hop-off tour lets you explore the city’s highlights without rushing or walking miles. It’s relaxing, flexible, and oddly romantic when you’re both just vibing to the commentary and snapping pics.
Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck
Get the VIP experience with this Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck, perfect for couples who want it all without the guesswork.
A private guide shows off the best of the city (landmarks, photo ops, and secret gems) with plenty of time to take it all in.
Then, end on a literal high note at the observation deck. It’s a curated date full of wow-factor without the decision fatigue.
360 Chicago
For a date that literally elevates your relationship, 360 Chicago delivers. With floor-to-ceiling glass and the famously nerve-wracking TILT attraction, it’s part thrill, part “hold me tighter.”
Enjoy panoramic views from 94 floors up while sipping cocktails in the sky-high bar. It’s scenic, surreal, and the ultimate love-is-in-the-air moment.
Ready to Make the Windy City Your Next Great Love Story?
Big city plans feel a lot less overwhelming when all the best things to do in Chicago for couples are already mapped out.
From low-lit dinners to skyline thrills, every memory made here adds a new layer to your love story.
Don’t wait until the last minute to start planning! Securing vacation packages through Tripster make it easy to bundle and save.
You can book everything from Chicago attractions, shows, and hotels in one place and skip the stress.
All that’s left to do is pack your bag and your favorite person. Chicago’s waiting—and it’s got romantic things to do in Chicago you won’t want to miss!
Things To Do in Chicago For Couples FAQs
Is Chicago a good destination for a couple’s weekend getaway?
Yes, Chicago is perfect for a weekend escape with a balance of culture, dining, and cozy attractions. Whether you’re into museums, scenic walks, or live jazz, the city offers just enough charm and adventure for two.
What’s the best time of year to visit Chicago as a couple?
Late spring to early fall (May–October) is ideal for couples, with comfortable weather and tons of outdoor events. Winter can be magical too, especially around the holidays, but plan for colder temps and indoor experiences.
Are there any unique date night experiences in Chicago?
Absolutely—try the Chicago Magic Lounge for a speakeasy-style magic show or take a cooking class together in the city. For something scenic, hop on a Lake Michigan dinner cruise or ride the Centennial Wheel at night.
What’s a good place to stay in Chicago for couples?
Look for hotels in River North, the Gold Coast, or near Millennium Park for easy access to romantic spots. Many boutique hotels offer spa services, rooftop lounges, or city-view suites perfect for couples.
How can I save money on couples’ attractions in Chicago?
Use platforms like Tripster to bundle attraction tickets, shows, and hotels for the best value. Passes like the Go City Chicago Explorer Pass also offer discounts on top sites.
Are there fun things to do in Chicago for active couples?
Yes! Walk or bike along the Lakefront Trail, kayak the Chicago River, or explore Lincoln Park Zoo. You can also try indoor skydiving at iFLY or a food-themed walking tour.
Where can we catch the best city views together?
Head to 360 Chicago or Skydeck Chicago for panoramic skyline views. Rooftop bars like Cindy’s Rooftop also offer stunning scenery with a side of cocktails.
Are there romantic indoor activities for cold or rainy days?
Definitely—spend the day at the Art Institute of Chicago, explore the Garfield Park Conservatory, or unwind at AIRE Ancient Baths. Cozy up with a live jazz set at Green Mill or share a fondue pot at Geja’s.
What should we pack for a romantic Chicago trip?
Pack comfortable walking shoes, layers for unpredictable weather, and a smart-casual outfit for a night out. Don’t forget a camera or smartphone—Chicago is photogenic and perfect for capturing memories together.
