BEST Things to Do for Valentine’s Day in Chicago (From a Local)

Spending Valentine’s Day weekend 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 and the weekend before.

Things to Do in Chicago on Valentine’s Day

Valentines Day hearts

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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 or around Valentine’s Day include:

Candlelight: Valentine’s Day Special ft. “Romeo and Juliet” and More – February 14 and 15

You can find the full list of candlelight concerts in Chicago here.

Live Jazz & Dinner for Two

Have dinner for two with craft cocktails while listening to live music at Le Piano (6970 N Glenwood), a cozy, elegant, and romantic venue.

Go Outdoor Ice Skating

Looking for a fun outdoor activity in Chicago? There are many places to go outdoor ice skating in the city.

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 (a must on any Chicago bucket list). Online ticketed reservations are required.

people ice skating in Chicago at Millenium Park on Valentine's Day weekend 2024

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.

outdoor ice skating is one of the best things to do in Chicago for Valentine's Day

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.

Visit the Field Museum

The Field Museum is one of the largest natural history museums in the world. Inside the museum you will see Maximo, the Titanosaur, the largest dinosaur that ever lived. (Click here to purchase an Early Access VIP Tour if you want to avoid crowds).

Where: Chicago’s Museum Campus, 1400 S Lake Shore Dr, Chicago, IL 60605 (detailed directions and parking information is available here)

Hours: Open 9am to 5pm (last admission at 4pm)

Cost:  Admission varies. Admission will be free for Illinois residents on Valentine’s Day.

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.

You can enjoy similar view over from the The Signature Lounge at the 96th.

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. Advance purchase of timed tickets is required.

Cost: Price varies depending on day. Admission is FREE for Illinois residents on Valentine’s Day (must be reserved online in advance).

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, where visitors can pet and feed bunnies. They are offering bunnies by candlelight special events on February 14 & 15.

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 Private Dance Lesson

Looking for a fun activity to do as a couple? Enjoy a romantic date night with a private dance lesson learning the tango. Enjoy a sweet dessert and bring your own wine to sip on during class.

Where: 3317 W Irving Park Rd

Cost:  $75 per couple. Find out more and purchase in advance here.

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.

This instagrammable museum is offering a Valentine’s Day Special Ticket Discount – two tickets for the price of one on February 14th only.

Where: 25 E Washington St., Chicago, Illinois

READ: Best Indoor Things to Do in Chicago on a Cold Day for more indoor Chicago attractions.

Go Outdoor Curling


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A post shared by The Gwen Hotel (@thegwenchicago)

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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A post shared by IO Godfrey (@iogodfrey)

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

Dine in the Dark While Blindfolded

Looking for a unique dining experience? Dining in the Dark 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.

When: February 11 and 14

Where: Hubbard Inn, 110 W Hubbard, Chicago, IL 60654

Cost:  $85 per person. Purchase tickets in advance here.

See the Orchid Show at Chicago Botanic Garden

If you ware willing to travel to the northern suburbs, you can soak up the color and fresh blooms of thousands of orchids and other tropical plants at this year’s Orchid Show: Magnified at the Chicago Botanic Garden.

On February 14, the show is open between 5 and 8 p.m. for Orchids After Hours, featuring cocktailsand light bites for purchase; separate ticket required

Where: Chicago Botanic Garden, 1000 Lake Cook Road, Glencoe, IL 60022 (24 miles north of downtown Chicago)

Cost: Price varies. See website for prices and to purchase tickets in advance.

Looking more things to do in Chicago? Here are the best things to do in Chicago in February.

As you can see there are many things to do in Chicago on Valentine’s Day weekend.

Planning a trip to Chicago? Check out my Chicago guides and itineraries:



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