14 Fun and Exciting Things to do in Chicago for Couples

You're finally planning that trip to Chicago with your better half, and you want to maximize your visit as much as possible. So, what's there to do for couples in Chicago? A lot! Here's our favorite list of curated options to suit all interests, whether you are looking for a fun outing, romantic activities or exciting flavors to savor around the city. Here are some of the best things to do in Chicago for couples. 

1. Catch a Broadway Show in one of Chicago's Iconic Theaters

For couples who love live theater, music, or comedy

Forget New York! With Chicago being home to more than 250 theaters, the top comedy scene, and five Tony Award-winning theater companies, there is a venue and performance for any couple looking for entertainment! Watch a Broadway show in the theater district, head to The Second City for a laugh, watch a live music performance, or venture to the neighborhoods for some independent shows. The Chicago Theatre is just one of many Chicago attractions for couples where you'll find something fun to do.

Chicago Theatre - one of the best things to do in Chicago

2. Make it A Night Out at CloudBar at 360 Chicago

For couples who love good cocktails and amazing views

Elevate date night or girl's night out with a night on the town from 1,000 feet up! For one of the most exciting things for couples to do in Chicago, head over to CloudBar at 360 CHICAGO Observation Deck to order an elevated cocktail (or a beverage from the regular menu) and be prepared to be wowed by the 360-degree views. Head up before dusk for a front-row seat of sunset views and hang out for nighttime grooves and atmosphere while admiring the twinkling lights across the dark Chicago sky.

Things to do in Chicago for couples

3. Bike Along the Chicago Waterfront Trail

For couples who love to explore cities by bike

Get a taste of local life and bike on the Chicago Waterfront Trail. This path, which allows for adequate lanes for runners, bikers, and walkers, spans 18.6 miles from Ardmore Avenue to the north and 71st Street to the south. Enjoy fabulous views of the lake and the city and explore the neighborhoods of Chicago, including Uptown, Lakeview, Lincoln Park, South Loop, Bronzeville, Edgewater, and Hyde Park. Rent a bike at Lakeshore bike rentals in hybrid, road, or carbon bike formats.

The Chicago Waterfront Trail

4. Dine and Dance on a Chicago Dinner Cruise on Lake Michigan

For couples that love to cruise

Plan a romantic night in Chicago on Lake Michigan. Dance, dine, and see some of Chicago's exciting landmarks like the John Hancock Building, Navy Pier, and the Buckingham Fountain. The onboard DJ, fully stocked bar, and giant board games will keep you and your loved one entertained. Available for brunch, lunch, and dinner. Cruises depart from Navy Pier year-round since indoor and outdoor sections are available.

A Chicago dinner cruise - one of the best things to do for couples in Chicago

5. Stroll Through the Glorious Chicago Botanic Garden

For couples who love the sights and smells of nature

Do you love the sights and smells of nature—the botanical kind? Explore the Chicago Botanic Garden. What could be more romantic than strolling through gardens together? Fortunately, the Botanic Garden is open all year for different experiences depending on the season. See the glorious gardens from spring to fall, then visit the Lightscape show during the winter holiday.

Lightscape is an outdoor show within the gardens of light, fire, music, and color. It's definitely an event that will brighten your evening enjoyment. Check out the monthly calendar of activities even if the flowers aren't blooming.

Chicago Botanic Gardens

6. Explore the World Under the Sea at the Shedd Aquarium

For couples who love animals

The Shedd Aquarium is one of the best Chicago attractions for couples because it's a place where age doesn't matter and makes for an exciting day out with your partner. Explore the wondrous aquatic animal world at the Shedd Aquarium. Join a guided tour to the must-see sections of the aquarium, sign up for the meet the otters encounter, or use the Shedd App to navigate your way through the aquarium and learn about the animals you want to see. Oh, what a world under the water!

7. Be in Awe at the Field Museum of Natural History

For couples who love to explore the world

The Field Museum of Natural History has something that will amaze any couple, even if they have different interests. Opening its doors in 1894, The Field Museum has a collection of over 40 million specimens and artifacts from all over the world that are bound to amaze anyone that walks through its corridors. The building itself has an incredible history of its own. There's always a new exhibit to explore.

The Field Museum of Human and Animal history in Chicago

8. Cruise the City from the River

For couples who love history and architecture

It's a tour through the city for views of Chicago's iconic architecture from the river. Join a tour with exciting narration and details of the legendary people who designed and built Chicago. Sit outdoors or indoors, then relax and enjoy the 90-minute tour. Find more information about a top-rated riverboat architectural tour. 

Chicago River Cruise - one of the best things to do for couples

9. Wet Your Whistle at Chicago's Craft Beer Scene

For beer-loving couples

Since Chicago was named the best beer city for its vast number of breweries, brewpubs, and beer bars, checking out the craft beer scene is a must for beer-loving couples. There is even a beer barrel bus tour to hit the top brewpubs (or distilleries and wineries, if you prefer). Choose from public tours or private events. Now that's a city that loves its suds.

Chicago barrel run tours to craft breweries

10. Go Ice Skating or RollerBlading Hand-in-Hand

For couples who love a romantic stroll together

Maggie Daley Ice Skating Ribbon is a lovely spot for skyline views, a fun atmosphere, and fresh air while striding hand in hand on skates. In winter, strap on some skates (rentals available) and glide around one of the coolest skating rink parks. In the summer, it is an excellent spot for rollerblading too. The park offers tons of romantic things to do in Chicago for couples who love spending time outside. Find out all the other things to do at Maggie Daley Park any time of the year.

11. Catch A Jazz Show At An Iconic Club

For nostalgia or jazz-loving couples 

It's the iconic jazz club of the city and is 100 years young. The Green Mill Jazz Club is a 1940s-style venue with live music seven days a week starting at 8 pm. It's an experience even if you don't frequent jazz clubs. The history of acts and famous patrons of this place is enough to visit it. Just like in the 1940s, it's a cash-only bar.

12. Scream and Laugh on TILT

For couples looking for a thrill

It's the thing to do in Chicago for thrill-loving couples. Take in the enjoyment of the Chicago skyline views, then tilt outward 1,000 feet above the Magnificent Mile. Find the TILT thrill ride at 360 CHICAGO Observation deck. Stay a while and discover the Chicago city views in full panorama. It's definitely a view worth screaming for.

13. Get Your Foodie On with the Tastes of Chicago

For Foodie lovin' couples

Sure, Chicago is known for Deep Dish Pizza, Italian beef sandwiches, and its infamous BBQ, but there is an endless array of flavors and styles of restaurants, diners, kiosks, and white tablecloth establishments to choose from. An easy way to navigate all these options is to visit Chicago during one of its food events celebrating its eclectic flavors. 

Here are a few of the top events: 

Chicago Restaurant Week is a 17-day festival from Jan 20-Feb 5th, honoring the city's top-billed culinary scene. Three hundred restaurants around the city participate in the event with special menus and offers. This is an excellent opportunity to explore the city and its cuisine. 

Taste of Chicago is a vast outdoor food festival in June and July, held every year with more than 1.4 Million locals and visitors sampling all the delicious bites. The event is a food and music festival at Grant Park.

There are so many more festivals in Chicago dedicated to food. Check out the Chicago Food Festival Guide and plan your visit around an event.

Food in Chicago and the tastes of Chicago festival and other food events

14. Drink and Dine with a View at the London House Rooftop

It's rooftop dining at its finest. Book a table for two and sit outside on the patio with views of the city and the Chicago River. Dine and drink with a modern take on American cuisine. If it's cold out, there are indoor options too. The London Rooftop hosts all kinds of events throughout the year.

The London House rooftop

There are so many fun things to do in Chicago for couples that you're guaranteed to find activities that fit your interests! For more fun activities over a weekend or vacation, check out the Romantic Things to do in Chicago.

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