The Top Romantic Things to Do in Chicago

View of Chicago's skyline and lake front.

GettyI mages-Sachin Saraswat / EyeEm

America’s third coast, home to 2.7 million people, is one of the most romantic destinations in the world. Twosomes, or singles open to chance encounters, can visit a planetarium and sip cocktails after hours, ride in a Ferris Wheel at a pier, learn how to ballroom dance, view the city lights from a twilight cruise and so much more. Colossus of the Midwest, Chicago has all the urban pleasures a couple could want. Here are the top romantic things to do in Chicago.

01 of 08

Flirt Above the City in a Helicopter

Chicago Helicopter Experience

 Chicago Helicopter Experience

Book a Private Date Night Experience with Chicago Helicopter Experience, one of Chicago's best tours, and see the Windy City from new heights. You’ll spend time in the lounge, playing games and relaxing, while you wait for your flight to take off. Once in the air, you’ll view the Chicago skyline and lakefront while your pilot points out Willis Tower, Navy Pier, Buckingham Fountain and the Magnificent Mile. Seeing Chicago’s architecture, lit up in the night sky, is truly a romantic way to spend the evening with your partner. The Date Night Experience also includes a $100 gift certificate to be used at the stylish The Duck Inn or the newly opened Monnie Burke’s, both located in Chicago’s Pilsen neighborhood. 

02 of 08

Learn About Space, with a Cocktail in Hand

Adler Planetarium Sundial

GettyImages- Franz-Marc Frei 

One of Chicago’s top museums, Adler Planetarium, caters to all ages and has special programming at night just for adults. The long-running Adler After Dark welcomes the 21-and-over set through its doors for evening access to shows, live entertainment and thematic events. You and your date will stroll hand-in-hand through the museum’s exhibits and galleries, watch award-winning sky shows, learn from the experts during space-themed lectures and scope out stars and planets in the Doane Observatory. Enjoy a cocktail or two, available at Café Galileo’s, and peek at Chicago’s glimmering skyline. 

03 of 08

Cruise the Chicago River at Twilight

Architecture cruise at dusk

TripSavvy / Anna Haines

Perfect for couples, Chicago Architecture Center’s Twilight River Cruise is both enlightening and dreamy. Board Chicago’s First Lady just as the sun sets, where you’ll meet a trained volunteer docent who will relay stories of Chicago’s past. You’ll learn about the different architecture as you float by more than 50 buildings along the Chicago River. Enjoy a snack or adult beverage from the bar and toast the night away. 

04 of 08

Explore a Romantic Neighborhood

Andersonville, Chicago

 Getty Images- James Andrews

Any Chicagoan will tell you that the true heart of the city exists in the neighborhoods. Take your loved one to historic Andersonville, a lovely neighborhood on the north side with Swedish roots, a thriving network of independent businesses, some of the top restaurants and bars, and one of the city’s largest LGBTQ+ population.

Shop at Alley Cat Comics, sample one of the beers on tap at Hopleaf or Simon’s Tavern, see an other-worldly show at the Neo-Futurist Theater, be entertained at Chicago Magic Lounge and learn about gin and whiskey at KOVAL through a tour or workshop. 

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05 of 08

Ride the Ferris Wheel at Navy Pier

Navy Pier

 Getty Images- Michael Lee

Navy Pier’s Centennial Wheel is a fun way to see the city’s skyline and lakefront from a new viewpoint. Experience this top Chicago attraction with your loved one, sheltered from the wind inside of a gondola. Purchase a Centennial Wheel VIP Gondola Buy-Out, a luxury experience that includes a ride in a posher cabin, with nicer seating and a glass bottom, for up to four guests. If you ride at night, you can see an LED light show, blinking from the wheel’s spokes. 

06 of 08

Indulge in a Couples Massage

Ritz-Carlton Chicago Spa

 Ritz-Carlton Chicago

One of the perks of a big city is access to luxury hotels that offer special services like couples’ massages and sedative body treatments. The Chuan Spa at The Langham Chicago, the Waldorf Astoria Spa and Health Club, the Spa at Four Seasons Hotel Chicago and the Ritz-Carlton Chicago Spa all offer extravagant treatments meant to help you relax, detox and breathe a sigh of relief. 

07 of 08

Watch the Sunset from a Skyscraper

View from 360CHICAGO

 Wendy Altschuler

View the Windy City’s skyline and Lake Michigan from 360 CHICAGO in the iconic John Hancock building. Home to TILT, a moving platform that slides you out over Michigan Avenue, 360 CHICAGO is the perfect date night. Arrive at night—the last admission is at 10:30 p.m., and plan on enjoying a beer from Revolution Brewing, served at Bar 94, Chicago’s highest bar. 

08 of 08

Dance with a Date

Ballroom dance lessons

 Getty Images/JackF

Connect with your partner and learn how to dance at Ballroom Dance Chicago. This 30-minute introductory private lesson is meant to be fun. You’ll work on basic movements with an instructor and then, if you’re interested in more, move on to hour-long lessons. Bring along your favorite wine, beer or beverage to make a proper date out of the experience. Group dance lessons are also offered and, if you don’t have a partner, you can still join in on the fun and meet someone new as a solo dancer. 

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