Date Ideas in Chicago

There’s no better way to spice up your relationship and add variety than to plan an unforgettable date night in Chicago! Whether you’re looking for something classic or out of the ordinary, there are plenty of creative ways to enjoy the city with your special someone.

From romantic strolls along Lake Michigan to intimate dinners on one of Chicago’s many rooftops—we have nine perfect date ideas for any couple who wants quality time together. So if you’re ready to plan the adventure of a lifetime, keep reading because these experiences will take your dating life (or marriage!) from ho-hum to fabulous!

Kayak Tour on the Chicago River or Lake Michigan 

Get ready for a day of adventure and breathtaking views with a kayak tour on the Chicago River or Lake Michigan. Choose from an afternoon paddle in the sun, a romantic sunset option, or a festive Happy Hour paddle, complete with a tiki party and complimentary beer at the Island Party Hut.

Fondue Feast at Geja’s Cafe 

If you’re looking for an interactive and indulgent dining experience, head to Geja’s Cafe for their famous fondue meal. From classic cheese fondue to decadent options like beef tenderloin, cold water lobster tail, and scallops, there’s something for every palate. And don’t forget the grand finale: the cafe’s signature Belgian chocolate fondue served tableside with marshmallows.

Urban Art Workshop 

Release your inner street artist at an Urban Art Workshop, where you’ll learn the ins and outs of spray paint and stencil application. Create your own original piece to take home and impress your date with your newfound creative skills.

Ancient Thermal Bath Experience at AIRE 

Indulge in the ultimate relaxation experience at AIRE, a one-of-a-kind spa in River West. Soak away your stresses in traditional Roman, Greek, and Ottoman-style baths with temperatures ranging from 102ºF to a chilly 50ºF. Try the aromatherapy steam room or swim in the heated indoor/outdoor pool. Add a couples massage or a wine bath for two for a truly luxurious experience.

Embark on an Artistic Adventure 

Take your date on a colorful journey along the 16th street walls in Pilsen. This outdoor gallery of murals showcases the work of both local and international street artists. Point out your favorite artworks and share your thoughts on their meanings. You’ll bond over your mutual appreciation for beauty and creativity.

Cruise Along the Lagoon 

For a vintage romantic experience, head to Humboldt Park and rent a swan boat to paddle around the park’s lagoon. You and your date can enjoy the tranquil scenery and each other’s company. Afterward, indulge in retro-inspired treats at Spinning J Bakery and Soda Fountain outside the park.

Watch a Movie in Style 

Instead of going to a regular movie theater, take your date to the Music Box. This historic theater boasts a grand 750-seat auditorium where you can watch foreign films or indie documentaries on the big screen. Snuggle up with your special someone and share some extra buttery popcorn.

Laugh Together at Live Theater 

For a unique and entertaining night out, visit The Neo-Futurist Theater in Andersonville. The Neo-Futurists have been pushing the boundaries of live theater for over 30 years. Their signature show, The Infinite Wrench, features 30 short plays in one hour that will leave you and your date in stitches.

Explore the Beauty of Nature

For a free and stunning date idea, visit the Garfield Park Conservatory. You and your date can wander through indoor rooms filled with exotic plant species, like towering palm trees and prehistoric ferns. Or, take a walk through the 10 acres of outdoor gardens and admire the beauty of nature.

Conclusion

With so many unique and fantastic date ideas in Chicago, it’s easy to find yourself having fun while creating lasting memories with your special someone. Whether you go the traditional route by having a romantic Fondue feast or get adventurous with a kayak tour on the river, there’s no shortage of ways to make the time spent together count.

If you’re looking for something more creative, why not explore your artistic side? You can embark on an artsy project with an Urban Art Workshop or ancient thermal bath at AIRE. For those who prefer to relax and take in their surroundings, there’s nothing quite like enjoying beautiful views from the lagoon or watching a movie in style.

And if laughter is preferable, experience live theatre together and bask in its hilarity. Whatever you’re looking for, rest assured that numerous date options await! So go ahead and explore the beauty of Chicago as you create new and inspiring stories each step of the way. If you enjoy this blog post, we’d love for you to share it with your community!