Spending Valentine’s Day in Chicago and looking for unique things to do instead of the usual dinner and drinks? Here are the most romantic things to do in Chicago for Valentine’s Day.
Things to Do in Chicago on Valentine’s Day (February 14, 2025)
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Attend a Candlelight Concert
Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. Some of the concerts taking place on Valentine’s Day include:
Candlelight Concert: Valentine’s Day Special – Friday, February 14, 2025, 6:30pm & 8:45pm
Candlelight Concert: Classical Romance – Friday, February 14, 2025, 7pm & 9pm
You can find the full list of candlelight concerts in Chicago here.
Love Struck – AirOtic Soirée
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: 7:00 pm. on select dates from February 6-March 1, 2025 including Valentine’s Day
Where: Joy District, 112 W Hubbard St, Chicago, IL 60654
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
Cost: Prices start at $29 per person. Click here to purchase tickets.
Ride the Ferris Wheel at Navy Pier
Couples can ride the Centennial ferris wheel for amazing skyline views (click here to purchase a fast pass ticket and skip the long line) and check out Flyover Chicago, an immersive flyover experience.
Go Outdoor Ice Skating
Looking for a fun outdoor activity in Chicago? There are many places to go outdoor ice skating in the city on Valentine’s Day.
One of the best and instaworthy places to go ice skating in downtown Chicago skating ribbon at Maggie Daley Park which has a path twice the length of a lap around a traditional skating rink. Online reservations required and will be released for Valentine’s Day on Monday, January 20, 2025.
You can find more places outdoor ice skating in Chicago here.
Take a Helicopter Tour
If you are able to splurge, a helicopter tour is one of the most romantic activities you can do for Valentine’s Day.
Admire Famous Works at the Art Institute of Chicago
The Art Institute of Chicago is one of the oldest and largest art museums in the United States and is frequently found on lists of the top museums in the world. In addition to its large permanent collection of art from around the world, you can see rotating exhibitions. (Click here to buy a skip the line ticket if you want to avoid long lines).
Where: 111 S Michigan Ave, Chicago, IL 60603
Hours: 11am– 5pm
Cost: Price varies. Entry is free for Illinois residents on Valentine’s Day.
See the Spring Flower Show at Garfield Park Conservatory
The Garfield Park Conservatory is one of the largest and most stunning botanical conservatories in the US. Often referred to as “landscape art under glass,” the conservatory showcases thousands of plant species from around the world throughout eight indoor display gardens. Reservations are required.
Starting February 14, visitors can see this year’s Spring Flower Show.
Hours: Open from 10am-5pm on Valentine’s Day
Where: Garfield Park Conservatory, 300 N. Central Park Ave., Chicago, IL 60624
Cost: Admission is free for Chicago residents
See the Spring Flower Show at the Lincoln Park Conservatory
Although not as large as the Garfield Park Conservatory, the Lincoln Park Conservatory is worth a visit and is more conveniently located for visitors. Advance online reservations are strongly recommended.
Starting February 14, visitors can see this year’s Spring Flower Show.
Hours: Open 10am-5pm on Valentine’s Day
Where: 2391 N Stockton Dr., Chicago, IL 60614
Cost: FREE
Enjoy the Views from 360 CHICAGO
Enjoy amazing views of the Chicago skyline from 360 CHICAGO (former John Hancock Building).
The 360 Chicago observation deck on the 94th floor is home to TILT, an enclosed moving platform that literally tilts you out over Michigan Avenue from the 94th Floor.
Where: 875 North Michigan Avenue, 94th floor, Chicago, IL 60611
Cost: Price varies. Click here to buy a skip the line ticket).
Visit the Shedd Aquarium
Visiting the Shedd Aquarium is a fun and relaxing daytime activity for couples.
Where: 1200 S. Lake Shore Drive, Chicago, IL 60605
Hours: Open 9 am – 5 pm.
Cost: Price varies depending on day.
Tip: If you are visiting a few museums and indoor attractions, consider purchasing a Chicago CityPASS or Go Chicago Card to save money on entrance fees.
Hold and Feed a Bunny
Looking for a unique thing to do in Chicago with your Valentine? Visit the Cuddle Bunny to snuggle with their cuddly bunnies (and each other) by candlelight. Reservations are required.
Where: Cuddle Bunny, 2901 N Clark St, Chicago, IL 60657
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
Cost: Price varies.
Take a Cooking Class
Looking for a fun activity with your loved one? You can take a hands on cooking class at The Chopping Block. You can find their class schedule here.
Where: Lincoln Square, 4747 N Lincoln, Chicago, IL 60625
Cost: Price varies.
Take Instagram Photos at the Museum of Illusions Chicago
The Museum of Illusions Chicago offers an interactive, immersive and fun experience for both adults and kids with exhibits that will teach you about vision, perception, the human brain and science.
Where: 25 E Washington St., Chicago, Illinois
Go Outdoor Curling
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Below is a list of places offering outdoor curling (along with drinks) on Valentine’s Day weekend:
Upstairs at The Gwen, 521 North Rush Street
Harry Caray’s Tavern – Navy Pier, 700 E. Grand Ave
Kaiser Tiger, 1415 West Randolph St
Have Drinks in an Igloo
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Here are some of the best outdoor igloos in Chicago (advance reservations are required).
Kennedy Rooftop, 1551 W North Ave
I|O at The Godfrey Hotel Chicago, 127 West Huron Street
Chicago Valentine’s Day (February 14, 2025) Events
In addition to the activities mentioned above, other events on and around Valentine’s Day include: Family Valentine’s Dance at Horner Park, Valentine’s Day Dance at Lake Shore Park, Chemistry in Nature: A Valentine’s Day Event at Field Museum (21+), Valentines Day Comedy Jam at European Chalet Banquets, Cem Yılmaz Show CMXXIV at Copernicus Center, Set Yourself on Fire: The 20th Anniversary Tour at Thalia Hall, Michigan Rattlers at Lincoln Hall, Nico Play at Schubas Tavern, Jeffrey Osborne at the Auditorium Theatre and Herencia de Un Rey: Homenaje a Vicente Fernandez at Old Town School of Folk Music – Gary & Laura Maurer Concert Hall.
Chicago Valentine’s Day Weekend Events
In addition to the activities mentioned above, other events during Valentine’s Day weekend include: Taylor Tomlinson Save Me Tour at The Chicago Theatre (February 12-15, 2025), So Sweet is Your Return at the Newberry Consort (February 14-16, 2025), Chicago Theatre Week (February 6-16, 2025) and Chicago Auto Show (February 8-17, 2025).
For more Valentine’s Day weekend events, bookmark this post about the best weekend events which is updated every week.
As you can see there are many things to do in Chicago on Valentine’s Day. If you are spending more time in Chicago, here are more things to do in Chicago in February.
Planning a trip to Chicago? Check out my Chicago guides and itineraries:
