You're finally planning that trip to Chicago with your better half or bestie, 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 two.
1. Catch a Broadway Show in one of Chicago's Iconic Theatres
For couples who love live theatre, music, or comedy
Forget New York! With Chicago being home to more than 250 theatres, the top comedy scene, and five Tony Award-winning theatre companies, there is a venue and performance for any couple looking for entertainment! Watch a Broadway show in the theatre 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 venues where you'll find something fun to do.
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! 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.
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.
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.
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.
6. Explore the World Under the Sea at the Shedd Aquarium
For couples who love animals
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.
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.
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.
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. 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.
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.
There is so much to do in Chicago as a couple that you are guaranteed to find things that fit your interests! For more things to do for couples for a weekend or vacation to Chicago, check out the Romantic Things to do in Chicago.
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