If you have a 3 or 4 day weekend for President’s Day, there are tons of things to do in Chicago on Presidents Day and even more during the weekend. Below are the best things to do in Chicago for President’s Day weekend from a local.
The Saturday before President’s Day is also Valentine’s Day so please see this dedicated post for Valentine’s Day themed activities.
I suggest bookmarking this blog post as will be updating it regularly with any new information and events.
Disclosure: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you.
Chicago Presidents Day Weekend Events
The best events taking place in Chicago during Presidents Day weekend include: Bingo Loco: The Ultimate Bingo Party (February 13, 2026), Dozin’ with the Dinos at the Field Museum (February 13, 2026), Winter Tequila Tasting Festival (February 14, 2026), Valentine’s Day Fireworks at Navy Pier (February 14, 2026), Josh Johnson The Flowers Tour at The Chicago Theatre (February 13-15, 2026), Chicago Theatre Week (Through February 15, 2026), Chicago Auto Show (Through February 16, 2026) and Chicago Black Restaurant Week (Through February 22, 2026).
Things to Do in Chicago on Presidents’ Day
In addition to the events listed above, below are more things to do in Chicago on Presidents’ Day (Monday, February 16, 2026).
Commemorate Presidents’ Day Family Event at the Chicago History Museum
The Chicago History Museum is having a family-friendly Presidents’ Day event featuring hands-on activities designed for families with young children.
Where: Monday from 10am-4pm
Where: Chicago History Museum, 1601 N. Clark St., Chicago, IL 60614
Cost: Included with admission, which is FREE for Illinois residents on this day.
Admire Famous Works at The Art Institute of Chicago
Chicago has many great museums which are worth visiting but my top pick is the Art Institute of Chicago conveniently located next to Millennium Park. It 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
Cost: Price varies. Must purchase tickets online in advance. Admission is free for Illinois residents this Monday.
Have Fun at Navy Pier
Navy Pier is a must if you are visiting Chicago with toddlers or kids. Fun attractions include a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line), rides and games, restaurants, shops, Flyover Chicago and the Chicago Children’s Museum.
Through February 16, 2026, visitors can take a stroll through Navy Pier’s illuminated Tunnel of Love along the South Dock which is adorned with giant hearts and twinkling diamonds, making it a great photo-op for Instagram.
Enjoy the Views from 360 CHICAGO Observation Deck
360 CHICAGO, the observatory on the 94th floor of the former John Hancock Building, has the best views of the Chicago skyline and Lake Michigan. (Click here to buy a skip the line ticket).
Where: 875 North Michigan Avenue, 94th floor, Chicago, IL 60611
Enjoy the Views from Skydeck Chicago
Skydeck Chicago in Willis Tower offers spectacular views spanning up to four states. Make sure to visit The Ledge, a glass balcony extending four feet outside the 103rd floor of Willis Tower. The Skydeck has implemented timed ticketing and they recommend reserving your tickets in advance to guarantee access. (Click here to buy a skip the line ticket if you want to avoid long lines).
Where: 233 S Wacker Dr, Chicago, IL 60606
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
Cost: Admission varies.
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.
Go Outdoor Ice Skating
Looking for a fun outdoor activity in Chicago? There are many places to go outdoor ice skating in the city. A picture perfect spot is the skating ribbon at Maggie Daley Park which has a path twice the length of a lap around a traditional skating rink.
Go Outdoor Curling
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Curling is a winter sport in which players slide stones on a sheet of ice or a lane towards a target. Below is a list of places offering outdoor curling (along with drinks):
Upstairs at The Gwen, 521 North Rush Street
Harry Caray’s Tavern – Navy Pier, 700 E. Grand Ave
Kaiser Tiger, 1415 West Randolph St
Things to do in Chicago during Presidents Day Weekend
If you are spending Presidents Day weekend in Chicago, you will find even more fun things to do. (And if you have more time, here are more things to do in Chicago in February.)
These activities are not available on Monday but are open on the weekend:
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 during Presidents Day weekend include:
Candlelight: 90s Unplugged
Candlelight: Ed Sheeran Meets Coldplay
Candlelight: The Best of Joe Hisaishi
Candlelight Valentine’s Day: Classical Romance
You can find the full list of candlelight concerts in Chicago here.
AirOtic Soirée Presents: LoveStruck
AirOtic Soirée Presents: LoveStruck is in Chicago for only a limited time in February. Enjoy 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.
Where: Experience 868, 868 N Franklin St, Chicago, IL 60610
Cost: Price varies. Click here for full prices and to purchase tickets in advance.
Enjoy the Spring Flower Show at the 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 Garfield Park Conservatory showcases thousands of plant species from around the world throughout eight indoor display gardens. Visitors can enjoy the lush flora and tropical temperatures indoors even if it is cold or rainy outside.
Starting February 14, 2026, you can also see the Spring Flower Show: Showers of Flowers.
Where: 300 N. Central Park Ave., Chicago, IL 60624
Hours: Closed on Monday but open on the weekend. Advance reservations are strongly recommended.
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.
Starting February 14, 2026, visitors can also enjoy the annual “Jewels of Spring” Spring Flower Show.
Where: 2391 N Stockton Dr., Chicago, IL 60614
Hours: Closed on Monday but open on the weekend from 10am-5pm. Timed entry reservation is required.
Cost: FREE
For more things to do in Chicago during Presidents day weekend, you can find more of the best weekend events here.
As you can see there are many things to do in Chicago on Presidents Day 2026 and even more on the rest of Presidents day weekend. 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:
