The most romantic things to do in Chicago for couples in 2026. Whether planning a weekend getaway in the city with your significant other or looking for unique Chicago date night ideas, these are the best activities to enjoy in Chicago with your partner.
Romantic Things to Do in Chicago for Couples (2026)
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Listen to Music at an Intimate Candlelight Concert
Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. Upcoming concerts include:
Tribute to Adele
A Tribute to Taylor Swift
The Best of Hans Zimmer
You can find the full list of current candlelight concerts in Chicago here.
AirOtic Soirée Presents: LoveStruck
Take your significant other to Love Struck – AirOtic Soirée, a Valentine’s themed burlesque-style cirque cabaret where sultry performances blend with dazzling cirque acts featuring world-class acrobats. Only for adults 21+ with valid ID.
When: Through February 28, 2026
Where: Experience 868, 868 N Franklin St, Chicago, IL 60610
Cost: Price varies. Click here for full prices and to purchase tickets in advance.
Watch a Drunk Shakespeare Play
Join The Drunk Shakespeare Society for an unforgettable evening of Shakespearean revelry. Set within a speakeasy, five actors attempt to perform a Shakespearean play after one of them downs multiple shots of various alcohols. Every show is different depending on who is drinking and what they’re drinking. Must be 21+ with valid ID.
Where: The Lounge At The Lion, 182 North Wabash Avenue
Go Outdoor Ice Skating
There are several places to go outdoor ice skating in Chicago. One of the best and instaworthy places to go ice skating in downtown Chicago is the McCormick Tribune Ice Rink right in front of The Bean. Another picture perfect spot is the nearby skating ribbon at Maggie Daley Park which has a path twice the length of a lap around a traditional skating rink.
Take an Architecture River Cruise
An architecture river cruise is a must on any Chicago bucket list. In addition to cruises throughout the day, there are also architecture river cruises at night for couples on a date night.
Enjoy the Views from 360 Chicago
360 CHICAGO (formerly John Hancock Observatory) on the 94th floor of the 875 North Michigan Avenue (the building formerly known as the John Hancock Center) has an observatory with great panoramic views of Chicago. The highlight is TILT an enclosed moving platform that tilts you out over Michigan Avenue. Click here to buy a skip the line ticket). You can also visit CloudBar which has a full 360-degree view of Chicago.
Ride the Ferris Wheel at Navy Pier
Navy Pier has several fun outdoor activities at Navy Pier including a large Ferris wheel (click here. Check out the Flyover Chicago, an immersive flyover experience.
Navy Pier is also the starting point for various sightseeing tours, boat rides and cruises.
Watch Fireworks
Navy Pier puts on free fireworks shows every Wednesday and Saturday night in the summer and other special occasions including Valentine’s Day and New Year’s Eve. You don’t have to visit Navy Pier to enjoy the fireworks, you can see them from various spots along the lakefront.
A romantic way to see the fireworks is on a lake or river fireworks cruise which will stop on the water for passengers to enjoy the show.
Relax in Thermal Baths at AIRE Ancient Baths
Relax and enjoy thermal baths, massages and exclusive rituals with your loved one at AIRE Ancient Baths Chicago. Inspired by the tradition of baths from ancient Roman, Greek and Ottoman civilizations, AIRE Chicago is located in a restored historical building lit by candlelight in River West.
Where: AIRE Ancient Baths Chicago, 800 West Superior St., Chicago, IL 60642
Visit a Conservatory
There are two conservatories in Chicago that make for a great warm escape on a cold or rainy day.
The Garfield Park Conservatory (300 N. Central Park Ave) is one of the largest and most stunning botanical conservatories in the US. Often referred to as “landscape art under glass,” the Garfield Park Conservatory showcases thousands of plant species from around the world throughout eight indoor display gardens.
The Lincoln Park Conservatory (2391 N. Stockton Drive) is a free public conservatory full of tropical palms and plants.
Take a Helicopter Tour
If you are able to splurge, one of the best ways to see Chicago is from a helicopter tour.
Take a Cooking Class
Take a cooking class together and learn how to make new dishes. Here are some cooking classes to consider:
French Macaron class
Fresh Handmade Pasta class
Intro to The Art of Sushi
Deep Dish Pizza class with Pizzeria UNO
Learn To Make Mole The Real Mexican Way Before Lunch
You can find more cooking classes at Eataly, Baker Bettie, Sur La Table and The Chopping Block.
Take a Candle Making Class
Looking for a unique and romantic date activity? Join one of these candle making class and create signature scented candles together:
Candle Making Class on Magnificent Mile (900 North Michigan Avenue, Level 6)
Forever Love! Couples Hand Casting +Candle Making Workshop at Above Average Candle Studio (3414 West Foster Avenue)
Love After Dark – Sensual Couples Candle Making Experience at Above Average Candle Studio (3414 West Foster Avenue)
90’s R&B Sing-A-Long + Mini Candle Making at Above Average Candle Studio (3414 West Foster Avenue)
Other Couples Classes
Join a couples class and create something unforgettable together:
Date Night on Fire: VIP wheel-Experience at Color Cocktail Factory (1142 W 18th St)
Couples Fragrance Making Workshop + Trivia Game at Above Average Candle Studio (3414 West Foster Avenue)
Have Drinks on a Rooftop
Have dinner and drinks at one of the city’s many rooftop bars and restaurants while enjoying amazing views. The most romantic rooftops in Chicago include:
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– LH ON 22 (85 East Wacker Drive) – Enjoy classic cocktails and small bites from the outdoor LH terrace of LondonHouse Chicago which offers great views of the Chicago River, Lake Michigan and the Magnificent Mile.
– Cindy’s (12 S Michigan Ave) – Restaurant and bar on the rooftop of the Chicago Athletic Association Hotel located across Millennium Park which offers panoramic instagram worthy views of Millennium Park and Lake Michigan.
– The J. Parker (1816 N Clark St) on the rooftop of the Hotel Lincoln with great views of Lincoln Park.
– Kennedy Rooftop (1551 W North Ave) on top of the Hyatt Place Wicker Park, has amazing skyline views.
Have Dinner at an Intimate Restaurant
Take your sweetie out for dinner at an intimate restaurant. Some of the most romantic restaurants in Chicago include:
– North Pond (2610 N Cannon Dr) – Michelin star restaurant inside Lincoln Park with beautiful views.
– Bavette’s Bar & Boeuf (218 W Kinzie St) -upscale steakhouse in an ornate, dimly lit wood and brick setting.
– Ella Elli (1349 W Cornelia Ave) – Italian-Mediterranean sharing plates and classic cocktails in an intimate setting.
– Geja’s Cafe (340 W Armitage Ave, Chicago, IL 60614) – fondue restaurant known for its romantic, intimate atmosphere.
Looking for more suggestions? You can find a list of the most romantic restaurants in Chicago here.
As you can see there are many romantic things to do in Chicago. For more things to do Chicago, bookmark this post about the best weekend events which is updated every week.
Planning a trip to Chicago? Check out my Chicago guides and itineraries:
