Things to do in Chicago

21 Memorable Chicago Date Ideas

The perfect date turns your stomach into a butterfly conservatory, and the Windy City offers plenty of things to do in Chicago.

Get Romantic at These Chicago Date Spots

Candlelit dinners and cheesy rom-coms aren’t the only ways to spend date night. Here are 20 romantic Chicago date ideas to help you get started. These romantic date night spots make Chicago a top contender for the “City of Love” title. 

1. Relax at AIRE Ancient Baths

The AIRE Ancient Baths experience pulls inspiration from the thermal baths of ancient Greek, Roman, and Ottoman civilizations. Housed in a historic 1902 factory, this spa features plenty of exposed brick, industrial columns, and soft, moody lantern light. 

With tubs that have plenty of room for two, you and your loved one will be polished and pampered side by side. You’ll breathe in the calming scent of lavender oil and sip aromatic wines as you soak and scrub like the ancients did. Book a Couples Experience to enjoy basalt stone massages right next to each other.

2. Visit One of Our Shows!

The original architects who designed Chicago share a trait with the performers of our shows: they believe the impossible is possible. With our roster of rotating shows revolving around the Windy City, you’ll find there are plenty of chances to bring your date and join us to watch a performance for one of our shows.

Visit our website to find tickets for Chicago shows and stay in the loop for when our shows land in the Windy City next.

3. Soak Up Some Sun at One of Chicago’s Beaches

A sunset over Lake Michigan is the pinnacle of romantic views, best shared with the person you love. For a private view of this natural spectacle, head to one of Chicago’s quiet lakeside retreats — just make sure you tear your gaze from each others’ eyes before twilight descends. 

Chicago’s beaches are typically open long into the night, so you can cuddle up after the sun goes down. Montrose Beach augments the sky with panoramic views of Chicago’s famous skyline. Or head to South Shore Beach for serenity and beautiful lakeside lounging spots.

Photographer: Virrage Images

4. Take a Stroll Along the Chicago Riverwalk

There’s no better way to forge a deeper connection with your partner than going on a brisk, heartfelt walk. The Chicago Riverwalk is an intimate setting for you to stroll shoulder-to-shoulder into a profound conversation. 

This 1.25-mile path winds through six different coves with charming personality. Located in River North, The River Theater is the spot to share a gelato beneath a tree, The Jetty has fantastical floating wetlands, and The Marina is the spot for a delicious meal.

As the sun goes down, gaze at the lights of Chicago that reflect off the water and sway to a groovy lineup of local performers that regularly grace the Riverwalk with their soulful sounds. 

Photographer: Wirestock Creators

5. Ride the Iconic Ferris Wheel at Navy Pier

The World’s Columbian Exposition took over Chicago in 1893, and its memory lives on in the form of the Centennial Wheel. The 264-foot marvel was built by George Ferris Jr. and gave exposition visitors a bird’s-eye glimpse of the Windy City’s maze of streets and skyscrapers. Since then, the wheel has remained a spinning symbol of Chicago’s artful ingenuity. 

Now, the Wheel doubles as a delightful date spot. At its home on Navy Pier, climate-controlled gondolas make for a comfortable orbit all year long, while slow speeds mean you’ll have plenty of time to get cozy on the trip around.

Board at sunset for a peek at the palette of pink and orange against Lake Michigan. Or set off on a nighttime voyage lit by the twinkling Chicago skyline.

Explore Chicago’s Vivid Nightlife for Couples

The Windy City comes to life when the sun goes down. Here’s where to whisk your beloved when it gets dark.  

6. Visit One of Chicago’s Renowned Cocktail Bars

A rich history of Prohibition-era speakeasies bathes the Chicago bar scene in intrigue and enchantment. Today, Windy City bars are less illicit and more innovative when it comes to their spirits. Dozens of hip cocktail bars dot the city, each of them serving up classic drinks with a modern twist just special enough for a special night out together. 

In Chicago, you’ll find boozy establishments that suit any mood, from chic library-themed bars to Asian-inspired menus. For an ultra-exclusive experience, head to the Milk Room, which only seats eight people at a time and mixes drinks with rare, vintage spirits, so you’re sure to taste something unique. 

7. Laugh the Night Away at a Famous Chicago Comedy Club

There’s nothing like watching your date dressed to the nines and snorting with laughter. Chicago’s comedy scene is wild and fresh enough to keep you giggling all night long and beyond. Whether it’s edgy, lighthearted, or rebellious jokes that tickle your fancy, you’ll find it tucked away in a Windy City comedy club, surrounded by vibrant neighborhoods and enticing restaurants. 

For a night of hilarity, try Zanies to see a headliner every night of the week. Or visit the iO Theater for classic Shakespeare tales gone horribly wrong. For a side of crispy-cheesy deep-dish pizza with your laughs, The Comedy Bar is an excellent choice.

8. Take in the Stunning Skyline Views at a Rooftop Bar

A quiet moment staring at the sparkling Chicago skyline is the crown jewel of any romantic night out. Add a glass of red and a plate of delicious canapés to share and you have a date that will live in your memory forever. Here, a host of rooftop bars ensure no stunning skyline view goes unappreciated. 

For all-weather enjoyment, Cindy’s and Roof on theWit are our picks. Both have a scrumptious selection of food and toasty protection from the Windy City chill. For a chic sky-high lounging experience, try the Nobu Hotel’s Chicago Rooftop. Inspired by contemporary Japan, you’ll share small plates as you sample the cocktail of the month — which doubles as an excuse to come back when the calendar changes. 

9. Get Grooving to Live Music at a Cozy Venue

Looking for an opportunity to hold each other tight? Immerse yourself in Chicago’s spirited live music scene. Genre has no limits here. Jazz players show off their exquisite artistry; local rock bands keep crowds jumping. You’ll find it all at the lively venues hosting the best of Chicago’s musical talent each night.

The Green Mill has been hosting live jazz since 1907 and still draws massive crowds to its starry stage. If indie rock is more your speed, try The Empty Bottle. It's beloved for its crisp acoustics and intimate atmosphere, perfect for date night.

Be Outdoorsy 

Natural wonders make for a down-to-earth rendezvous. Fall in love amidst the fruits of the earth in Chicago’s outdoor gardens. Or explore nearby hiking trails in Chicago for cheap date ideas.

10. Visit the Lincoln Park Zoo

If it’s casual, fun activities you’re looking for, feast your eyes on the Lincoln Park Zoo. A quirky idea for adults, the universal appeal of the zoo date will hit you the second you’re face-to-face with a tiger. Nurture your shared nostalgia by pointing out your fuzzy favorites and reminiscing about childhood memories long passed.

Free admission means easy access to hours of fun and extra cash you can spend on a decadent meal afterward. If you need a break from the excited squeals of zoo-goers, head to the Nature Boardwalk for a stroll around the pond. If you’re looking for more family-friendly outings, check out these things to do in Chicago with kids.

11. Take a Cruise on Lake Michigan

Fewer things feel more luxurious than a sunset cruise across Lake Michigan. Treat your partner to a twilight sail with the Chicago skyline in your rearview.

After sharing a gourmet deck-side dinner, stand against the rail and feel the fresh wind ruffle your hair. And as you’re holding each other close for warmth, you’ll simultaneously be forming memories that will last a lifetime. 

12. Discover the Beauty of the Chicago Botanic Garden

Even a concrete jungle like Chicago makes space to celebrate the natural world. And with 385 acres of nature, the Chicago Botanic Garden offers plenty of room to breathe in the lush beauty of a plant-filled oasis. Here, the gardens change with the seasons.

Spring visits show budding flowers and busy bees, while summer brings a rainbow of riotous colors. During fall, the leaves change, and the bare branches of winter reveal their own stark beauty. Come back again for a stroll that marks your relationship’s evolution alongside the earth’s.

Of course, it doesn’t need to be that deep. Even a single visit presents a prime opportunity for lounging on the grass and feeling nature’s energy seep into your bones in tandem. 

Draw From Creative Inspiration

The fruits of creative labor can evoke powerful emotions. Share this sense of wonder with your partner at these art-loving date destinations.

13. Admire World Class Exhibits at the Art Institute of Chicago

Art, and how you feel about it, can spark a profound conversation. For a date that goes below the surface, head to the Art Institute of Chicago, where plenty of thought-provoking pieces dot the collection.

From household names such as Van Gogh and Picasso to unexpected pieces and artists you’ve never heard of, you’ll find it on the crisp-white gallery wall of the AIC. 

Take the stairs down to the basement for a gander at the AIC’s quirkiest exhibit: a giant room stuffed with miniature dioramas. Each of the 68 itty-bitty rooms and furnishings was designed and built by artisans and expert craftsmen for authenticity — all down to the smallest art deco chair. It’s a dedication to be admired. 

14. Take Pictures at "The Bean" in Millennium Park

Officially named “Cloud Gate,” The Bean has become a Chicago mascot. Its shiny, curved exterior reflects the ever-changing crowd of onlookers passing through Millennium Park, juxtaposed with the constant concrete skyline. Though seemingly little more than a tourist attraction, this thoughtful art installation will provoke something within you, whether it’s surprise, awe, or thrill.

The shifting nature of this sculpture means every picture you take will be different, giving you a full catalog of the day’s memories. Frame some of the best pictures to hang on your wall for a long-lasting reminder of this special date. 

15. Explore a Local Art Gallery

Wandering into a local gallery always evokes a sense of exhilaration. After all, you never know what you’re going to find. The artists creating these gems are more likely to take risks with their collection, so you'll see art that’s wild, whimsical, and maybe even controversial.

These galleries tend to be less crowded, so you can peruse the space at your leisure. And if you’re the couple that gets loud and zany, there won’t be anyone listening in as you debate the artistic merits of each piece.

16. Take a Historical Tour

Mrs. O’Leary’s cow may have burned down a large part of the city back in 1871, but there’s still plenty of Chicago history to explore. Historical tours tend to focus on the niche, unexpected, or bizarre, so even lifelong Chicagoans have something to learn. The tidbits you gather will inspire passionate dinner conversation for weeks. 

17. Embark on an Architectural Boat Tour

Chicago’s celebrated skyline is spotted with historic feats of architectural ingenuity — and there’s no better place to discover them than on the water. Jumping on an architectural boat tour gives you an unimpeded glimpse of the city’s breathtaking buildings.

There are more than 50 significant structures along the river, and seeing them from the water gives you a unique perspective that doubles as a fun river romp. The Chicago Architecture Center offers a beloved tour hosted by witty architecture experts.

To up the romance factor, join the evening tour and see the buildings by the light of the setting sun while sipping a cocktail. 

Photographer: Josh Hunnicutt

18. Spend the Day Exploring the Museum Campus

Museum Campus is a vibrant area in the heart of Chicago offering a wide collection of cultural, natural, and sporting venues all vying for your attention. You and your date can wander wherever you fancy, from the Field Museum to Adler Planetarium.

A more active day is best spent on Northerly Island Park, with its colorful bird sanctuary and maze of walking paths through a tranquil lagoon. 

Indulge Your Taste Buds

The best way to woo a person is through their stomach, especially those with a sweet tooth. Here are the best foodie date ideas in Chicago for your next tasty outing. 

Photographer: Rudy Balasko

19. Enjoy a Picnic at Grant Park

Grant Park hides a dreamy picnic spot in the middle of the central business district. Delectable nearby restaurants make it perfect for grabbing a long lunch together on the lush green lawn or listening to the bubbling water of Buckingham Fountain.

Show off your cooking skills with a basket full of homemade delicacies, or pick up a sandwich to share on a crisp Windy City afternoon. This expansive park offers plenty of private places to find solitude as you snack and enjoy each other’s company. 

20. Indulge in a Food Tour of Chicago’s Culinary Scene

Chicago is flecked with so many notable dining experiences. It’s almost impossible to sample them all. There’s deep-dish pizza and Chicago-style pizza, which are surprisingly not the same thing. But whichever style you choose, your date will love a Chicago Food Tour. Whether it’s street food, pastries, or pizza that gets your mouth watering, there’s a food tour with the fare for you.

As a local cuisine expert leads you across the city, you’ll taste a collection of dishes from some of the most drool-worthy eateries in the Windy City. Try as many as you can, then come back to your favorite later for a deeper exploration of the menu. 

Photographer: Pixel-Shot

21. Learn to Make a New Dish Together at a Cooking Class

New culinary exploits make for memories that last a lifetime. Your heart will start pounding as you both reach for the spatula, cheeks burning as you fish bits of eggshell out of cookie dough batter. It’s the recipe for a perfect date — one you’ll look back on well into the relationship.

Pick a cuisine you both love, take turns introducing each other to your favorites, or try something completely new. The Windy City offers a world of variety in its cooking classes, so tie up your aprons and let your taste buds be your guide. 

Make a Love Connection in the Windy City

Fun date ideas can electrify any relationship, whether it’s brand new or years in the making. Come to our shows and enjoy wonderful acrobatics and pulsing music with your special partner. These high-flying shows are filled with fantastical feats, stunning visuals, and touching storylines that turn any ordinary evening into a night to remember.

Find your spark together with a performance bursting with wonder. Get your tickets to a show in Chicago today in preparation for the perfect date night. 

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