10 Best Things to Do for Couples in Chicago

The Navy Pier is filled with dining and entertainment for all. However, as a couple you can escape on the iconic Centennial Wheel, which rises in the pier’s centre, overlooking Lake Michigan. The Ferris wheel offers a wonderful private experience for around $125. This lets you ride in a VIP gondola that’s specially fitted with plush seating and has a glass floor so that you can huddle together and enjoy the thrilling views. In the summer, fireworks synced to music add to the magic on Wednesdays and Saturdays.

Big and tall Amish workhorses meet big city life in Chicago. They provide memorable carriage tours through the city. A few operators serve Michigan Avenue. For the determined, it can be a most unforgettable way to pop the question. For any couple, it’s a great way to sightsee along the northern shopping section of the Magnificent Mile. Carriage rides at night can be charming, with the pretty shops and small churches along the way. Be sure to make use of the single blanket, for both of you to cuddle up under through the Windy City.

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 are the 114-foot Manitou and the 148-foot tall ship Windy of Chicago, both of which sail 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.

This high-rise Chicago landmark is one of the city’s iconic cultural beacons. Boasting French Baroque architecture and stretching up 7 storeys tall, it captures all the splendour of a trip to the theatre in the early 20th century. You can enjoy a show together here while admiring the magnificent interiors. Or, on separate theatre tours, you can stand in the lobby, look up and admire the crystal chandeliers and gilded décor of the grand space that’s inspired by the Royal Chapel at the Palace of Versailles near Paris, France.

The Chicago Helicopter Experience 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 glittering skyline, lit with millions of city lights.

Chicago is easily one of the best cities in the Midwest for cycling, thanks to its great collection of park trails and scenic flat routes that interconnect its neighbourhoods. An all-time favourite is the Chicago lakefront trail, which covers 20 miles along the western shore of Lake Michigan. For couples, tandem biking can be a fun and intimate way to enjoying 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.

Take your significant other for thrilling sensations from some of the world’s tallest skyscrapers. There’s 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 over at 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 often has couples clinging to each other for dear life.

You can find this popular spot 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, which are filled with 25 display gardens and 4 natural habitats. Among the favourites are the aquatic garden, the bonsai gallery, the Regenstein fruit and vegetable garden, the beautiful and Zen-like Elizabeth Hubert Malott Japanese Garden, and the Model Railroad Garden that families with kids will love.

When you’re looking for some swanky spot to take that special someone out on a date in Chicago, the Green Mill Jazz Club on Broadway Street takes some beating. The very place that was known as one of the favourite 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. Their weekly performance schedule is quite a full one, and the soulful jamming usually extends well into the wee hours.

The skyscraper-filled Windy City has plenty for couples looking for sky-high dining. Among them is the Signature Lounge on the 95th floor of the John Hancock building in Downtown. It offers romantic settings with amazing sunsets, where you can dine and drink to the city’s gradually emerging twinkling lights around the stunning Willis Tower. Cite, an upscale American restaurant with French influences, offers sweeping views of the city and Lake Michigan from the top of Lake Point Tower on North Lake Shore Drive.