The most romantic things to do in Chicago for couples in 2025. 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 (2025)
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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:
Candlelight: A Tribute to Taylor Swift
Candlelight: A Tribute to U2
Candlelight: Tribute to Adele
Candlelight: Tribute to Fleetwood Mac on Strings
Candlelight: The Best of Hans Zimmer
You can find the full list of current candlelight concerts in Chicago here.
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
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 Candle Making Class
Looking for a unique and romantic date activity? Join one of these candle making class and create signature scented candles together:
Love After Dark: Couples Candle Making Class at Above Average Candle Studio (3414 West Foster Avenue)
Couples Chocolate & Wine Tasting + Candle Making at Above Average Candle Studio (3414 West Foster Avenue)
Candle Making Class in Downtown Chicago at Reggie Hathorn (900 North Michigan Avenue, Level 6)
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
Asian Dumplings class
Learn To Make Mole The Real Mexican Way Before Lunch
You can find more cooking classes at Sur La Table and The Chopping Block.
Dine in the Dark While Blindfolded
Looking for a unique dining experience? Dining in the Dark at About Last Knife (168 Michigan Avenue) is a gastronomical experience that invites you to explore the full potential of your taste buds in a uniquely entertaining atmosphere. While blindfolded, you’ll enjoy delectable surprise dishes and feast on an entire meal without using your sight, thereby enhancing your other senses. There are three menus to choose from including a vegan option.
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.
Take a Lake Cruise
If you enjoy being on the water, a lake cruise is also a fun activity at night during the warmer months. While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views. If your time is short, you can do a combination river and lake cruise.
Watch Free Summer Fireworks at Navy Pier
Navy Pier puts on a free fireworks show in the summer twice a week (every Wednesday and Saturday night) between Memorial Day weekend and Labor Day.
In addition to summer fireworks, Navy Pier also has free fireworks shows on special occasions including Valentine’s Day, New Year’s Eve and the holiday season.
While you can watch the fireworks from Navy Pier, you can also watch it from various spots along the lakefront and some restaurants and bars.
One of the most romantic way to watch the fireworks is on a fireworks lake or river cruise which will stop on the water for passengers to enjoy the show.
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.
Look for Street Art
Another fun activity for couples is walking around the city looking for street art.
One of the most famous murals in Chicago is Greetings From Chicago Mural at 2226 N Milwaukee Ave, in Chicago’s Logan Square neighborhood. You can see this mural and other street art on this street art tour.
Listen to Free Outdoor Music Concerts in the Summer
One of the best things for couples to do in Chicago in the summer is listening to free concerts at the Jay Pritzker Pavilion in Millennium Park.
The annual Grant Park Music Festival (from June 11– August 16, 2025) is the only free outdoor classical-music concert series in the US. It features the Grant Park Symphony Orchestra and Grant Park Chorus along with guest performers and conductors.
The Millennium Park Summer Music Series (Mondays & Thursdays from June 26–August 7, 2025) features a wide variety of music from established and emerging artists at the iconic Jay Pritzker Pavilion.
Watch Free Movies in the Park
There are several places you can watch free outdoor movies in Chicago in the warmer months including Gallagher Way in Wrigleyville, Millennium Park and various public parks throughout the city.
Watch Classic Movies on a Rooftop
Want to watch classic movies against the backdrop of the Chicago skyline? Check out Rooftop Cinema Club outdoor screening series to a rooftop in Fulton Market.
Rooftop Cinema Club is located on the fifth floor terrace of The Emily Hotel (311 N Morgan St) and is a high end movie experience complete with tropical decor, lawn games, state-of-the-art LED screens, individual wireless headphones and a range of seating options including lounge chairs and loveseats. Guests can also order drinks and snacks. You can purchase tickets in advance here.
Watch Digital Art at Art on theMart
Art on theMART is the largest permanent digital art projection in the world, projecting contemporary artwork across the 2.5-acre river-façade of theMART. Free 30-minute program of projections are shown every night on Thursdays through Sundays. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.
Walk the Lakefront Trail
What is more romantic than a walk on the beach? Couples can walk along the Lakefront Trail, a paved path on a 18-mile-long stretch along Lake Michigan.
There are numerous beaches along the way if you want to stop for a picnic on the beach. Don’t forget to pack your beach essentials!
Even if the weather is too cold to enjoy the beach, the Lakefront Trail has some of the best spots to sit down, relax and enjoy Chicago skyline views.
Here is a map of the Lakefront Trail as well as its access points.
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.
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.
Planning a trip to Chicago? Check out my Chicago guides and itineraries:
- Weekend in Chicago: 3 Day Itinerary (According to a Local)
- The Perfect Itinerary for One Day in Chicago
- Most Instagrammable Places in Chicago
- Best Free Things to Do in Chicago
