Couple enjoying the American Writer’s Museum
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An insider’s guide to the most romantic evenings in The Second City
From its shimmering skyline to its intimate, low-lit bars where conversation lingers, Chicago exudes romance at every turn. Whether you’re museum hopping amidst dinosaurs and mummies, laughing until it hurts at the famed Second City comedy club, or toasting while on a sunset cruise on Lake Michigan, Chicago sets the stage for unforgettable date nights. Use this guide to embark on a romantic adventure with your special someone to Chicago’s favorite spots, where romance is in the air and the fun practically guarantees heart eyes.
Illuminated Navy Pier Fountain
Lake Views: As the sun sets, Chicago’s charm becomes irresistible. A classic Chicago date night begins with a stroll on the Chicago Riverwalk. Walk hand-in-hand along Lake Michigan’s serene shore and explore the city’s many famous sights. Landmark highlights along the path include the grand Buckingham Fountain, Navy Pier’s Centennial Wheel and the famed Cloud Gate (nicknamed "The Bean"), perfect for a selfie with your date. For the best view of it all, Cindy’s Rooftop serves cocktails and New American fare under a glass atrium 13 floors high above Millennium Park.
Architectural boat tour along the riverwalk
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Water Ways: Float on by Chicago’s scenic skyline and marvel as it transitions from daytime bright to a mesmerizing cascade of sparklingly-lit facades. The best way to enjoy the Chicago River is cruising on it, especially on one of the city’s popular architectural boat tours. Opt for a Lake Michigan sunset cruise for the most sweeping views of the city during golden hour.
Picture-Perfect Parks: Lincoln Park is one of Chicago’s most treasured parks, boasting an expanse of well-maintained parkland and beaches. Date nights here are seamless, as you share the joys of the free Lincoln Park Zoo, stroll through the orchid gardens of
Lincoln Park Conservatory and relax at North Avenue Beach. Other city parks perfect for a picnic include Grant Park, lovingly referred to as “Chicago’s front yard,” and Northerly Island Park, one of Chicago’s newest parks on the grounds of a former airstrip.
Couple admires captivating artwork at the Art Institute
choose chicago \ Abel Arciniega
Creative Chemistry: Let the sparks fly as you experience some of Chicago’s enchanting art institutions together. The Art Institute of Chicago is home to an extraordinary collection of masterpieces. For some date night fun, head to the museum for their special After Hours every Thursday evening and strike a solemn pose in front of Grant Wood’s iconic “American Gothic.” For contemporary and abstract art lovers, the Museum of Contemporary Art Chicago’s rotating exhibitions provide ample inspiration for lively conversations. If you’re more interested in creating your own art, Bottle & Bottega is the spot to sip wine and paint together.
Tickets for Two: Chicago’s performing arts are world-class. On any given night, you’re able to catch a play that’s likely on its way to Broadway from the Goodman Theatre or Steppenwolf, delight in one of the world’s greatest opera singers at the Lyric Opera of Chicago or be immersed in the sweeping aural bliss of the Chicago Symphony Orchestra. The Second City comedy club is one of the world’s most legendary comedy clubs. Snag your tickets for a show and take note of all the names on stage; you never know who could be the next Tina Fey, Dan Aykroyd or Jordan Peele—all who got their start on that very stage.
Traveler’s Tip: From Second City shows to boat cruises, date-night favorites can fill up fast. To avoid disappointment, be sure to buy tickets at least a week in advance. Get Tickets with AAA.
Intimate Appeal: Impress your date with one of Chicago’s many hidden gems and you’ll set the scene for an unforgettable night out. Chicago Magic Lounge is a stylish speakeasy with a unique, playful entrance hidden behind a laundromat. Once you’ve made your way through the secret passage, you’ll be seated for mind-bending magic tricks and craft cocktails. Jazz Showcase is Chicago’s go-to jazz bar. This is the city’s oldest continuously operating jazz club, and it packs in crowds nightly for an 8 PM & 10 PM set (plus a 4 PM Sunday matinee). Book your tickets in advance, as weekend nights often sell out quickly.
Game Night: Add in a touch of competition to your date night, and Chicago will rise to the occasion. Emporium Arcade Bar is Chicago’s original arcade bar, with three locations in the city. Challenge each other to classic arcade games, dozens of pinball machines and, of course, Skee-Ball. Puttery Chicago is immersive mini-golf at its best, with two courses, four bars and plenty of fun photo ops. Take your date to another dimension with the help of KRYPTON VR Lounge, a virtual reality gaming destination featuring over 55 VR experiences.
Quirky Adventures: Go off the beaten path for some of Chicago’s most unique and alternative fun date nights. Your chance to shine has arrived, well, if only just for you and your date. Private karaoke rooms at Lincoln Karaoke are the best way to sing your heart out, without having to worry if you’re being too loud. There’s also Chicago’s original Escape Artistry Escape Rooms, a local favorite that features Chicago-themed plots as you navigate your way out of the room. If you’re looking for Chicago’s zaniest night, head to BATSU! This underground smash hit is part dinner theater and part Japanese-style comedy game show, and all belly laughs.
Sports Fun: Chicagoans stay active year-round, thanks in part to the city’s numerous fun sports activities. Catch some serious air at iFLY Indoor Skydiving, the city’s skydiving simulator complex. Only at iFLY can you experience the pure joy of floating midair without having to jump out of a plane. If you’d rather send a golf ball soaring, Topgolf Swing Suite is the place to be. Topgolf’s new concept features indoor sports simulators with innovative new ways to enjoy golf, hockey, football and baseball. AceBounce’s ping pong tables offer the ultimate one-on-one challenge. The vibe here is friendly and upbeat, with elevated bar food that makes for some fun shareables. Don’t miss the garlic parmesan cheese curds and the deep-fried ranch bites.
Traveler's Tip: Discover helpful planning resources for hotels, dining and things to do in Chicago with AAA TripCanvas.
Information about attractions, restaurants and other businesses was accurate at the time of publication. Offerings, hours and availability may change, and some locations may have closed since. We recommend checking directly with the business before visiting.
