10 Best Things to Do for Couples in Chicago

Filled with dining and entertainment for all, the scenic Navy Pier waterfront offers couples an escape on the iconic Centennial Wheel, which rises in the pier’s center, overlooking Lake Michigan.

The Ferris wheel offers a wonderful private experience that lets you ride in a VIP gondola specially fitted with plush seating and has a glass floor so that you can cuddle together and enjoy the thrilling views. In the summer, fireworks synced to music add to the magic on Wednesdays and Saturdays.

The Chicago Riverwalk is undoubtedly one of Chicago’s most beautiful locales, offering a picturesque retreat from the city’s hustle and bustle. This 1.25-mile (2-km) promenade, located on the south bank of the Chicago River, boasts lush lawns, gardens, and scenic spots, punctuated by restaurants ideal for intimate riverside dining.

Beyond the leisurely strolls, the Chicago Riverwalk also provides a variety of activities. From embarking on a boat tour for unbeatable cityscape views to delving into some culture at the nearby museums, the riverwalk is an urban oasis with plenty to explore.

As one of the Great Lakes, Lake Michigan is the playground for several majestic yacht and tall ship cruises. Setting sail on the calm waters of the lake can be one of the most surreal experiences for romantics in Chicago.

Among the prominent ships is the 148-foot Tall Ship Windy, which sails the lake by day and in the evenings from Chicago’s Navy Pier. These sailing trips let you take in Chicago’s famous skylines and explore the city’s architectural wonders from the lakefront.

The Chicago Theatre is one of the city’s iconic cultural beacons. With its towering 7-story edifice showcasing exquisite French Baroque architecture, it captures all the splendor of a trip to the theater in the early 20th century. From magnificent Broadway shows to concerts with the biggest names in music to hilarious comedy shows, this theater provides endless nights of entertainment with your sweetheart.

While attending a show here, you can revel in the magnificent interiors. Alternatively, you can attend a separate theater tour. As you stand in the lobby, look up and admire the crystal chandeliers and the gilded décor of the grand space that’s inspired by the Royal Chapel at the Palace of Versailles near Paris, France.

The Fly Heli Chicago lets you go on a once-in-a-lifetime tour, with unparalleled views above the Windy City and its spectacular lakefront.

Daytime tours enable you to take flight and come to eye-level with Chicago's iconic skyscrapers. Most tours are guided, with the pilot narrating as you fly over the city’s most iconic landmarks. They’ll show you the best photo opportunities around the town, with a few bits of its rich history occasionally thrown in. Night flights are also available, showing you a glittering skyline lit with millions of city lights. If you’re planning to pop the question, don’t forget to check out the Marry Me Tour.

The Chicago Lakefront Trail is a testament to the city's reputation as one of Midwest's best cities for cycling, given its vast network of park trails and scenic flat routes. This 20-mile trail traces the western shore of Lake Michigan, offering a picturesque biking experience.

For couples, tandem biking can be a fun and intimate way to enjoy Chicago’s most beautiful outdoors. There are numerous bike rental companies providing tandem bikes, mostly with free locks, helmets, and even maps to help you navigate. 

Treat your loved one to an exhilarating experience by visiting Chicago's observation decks at some of the world's tallest skyscrapers. Check out the SkyDeck Ledge at the Willis Tower on South Wacker Drive. On its 103rd-floor edge, you can step into glass boxes which extend out, with your feet seemingly hovering in the air 1,300 feet above the ground.

Another observation deck, 360 Chicago, offers a similar sensation from the 94th-floor observatory of the John Hancock Building. Its lookout has a tilting glass enclosure that provides couples with heart-pounding views.

The popular Chicago Botanic Garden is located in Chicago’s rich collection of beautiful green oases in Glencoe, around a half-hour’s drive north from The Loop. The botanic garden spans over 380 acres and is home to 28 meticulously designed display gardens and 4 natural areas.

Perfect for couples seeking a unique experience, the Chicago Botanic Garden offers a variety of attractions. Relish the tranquility of the stunning Aquatic Garden, marvel at the intricacy of the Bonsai Collection, or stroll hand-in-hand through the serene and Zen-like Elizabeth Hubert Malott Japanese Garden, a space that is sure to captivate and inspire romance. 

When you’re looking for a swanky spot to take that special someone out on a date in Chicago, the Green Mill Jazz Club on Broadway Street is hard to beat. The very place that was known as one of the favorite hangouts of Al Capone is now a chosen spot for romantic dinners and relaxing with a selection of delicious signature cocktails accompanied by live jazz.

The club offers a packed weekly performance schedule, ensuring there's always a show to catch. The soulful jamming often continues into the early morning.

The skyscraper-filled Windy City has plenty for couples looking for sky-high dining. As the sun sets over the Windy City, a romantic rendezvous awaits couples at LondonHouse Chicago Rooftop. Perched in Chicago's impressive skyline, this unique dining location offers a spectacular dining experience, with panoramic views and vibrant city lights twinkling below.

For an even more elevated experience, try the VIP dining experience at Skydeck Chicago’s Restaurant on the 103rd floor. Its “Pie in the Sky” dinners are a must-do for couples looking for a unique Chicago experience.