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 (Monday, February 17, 2025) and even more during the weekend. Below are the best things to do in Chicago for President’s Day weekend from a local.
The Friday 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 2025 Events
Major events taking place in Chicago during Presidents Day 2025 weekend include: Winter Tequila Tasting Festival (February 15, 2025), Dozin’ with the Dinos at the Field Museum (February 15, 2025), Hyde Park Handmade Artisan Bazaar (February 16, 2025), Chicago Theatre Week (through February 16, 2025) and Chicago Auto Show (through February 17, 2025).
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 17, 2025).
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. Kids can write a “Letter to the President” which will be mailed to the White House.
Where: Monday, February 17, 2025 from 10am – 2pm
Where: Chicago History Museum, 1601 N. Clark St., Chicago, IL 60614 United States
Cost: Included with admission, which is FREE for Illinois residents on this day.
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. Click here to purchase tickets in advance.
Where: The Lounge At The Lion, 182 North Wabash Avenue
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 on Monday, February 17, 2025.
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.
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. Tickets for President’s Day weekend will be released at 12:00pm (noon) on January 20, 2025.
Take an Architecture River Cruise
If you are visiting Chicago for the first time don’t mind the chilly weather, take an architecture river cruise for great views of the Chicago skyline.
Go Outdoor Curling
View this post on Instagram
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 Concert: A Tribute to El Divo de Juárez
Candlelight: Valentine’s Day Special
Candlelight: Classical Romance
You can find the full list of candlelight concerts in Chicago here.
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.
During Presidents Day weekend, you can also see the Spring Flower Show.
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.
During Presidents Day weekend you can also check out their Spring Flower Show.
Where: 2391 N Stockton Dr., Chicago, IL 60614
Hours: Closed on Monday but open on the weekend from 10am-5pm. Advance online reservations are required.
Cost: FREE
For more things to do in Chicago during Presidents day weekend, bookmark this post about the best weekend events which is updated weekly.
As you can see there are many things to do in Chicago on Presidents Day and even more on the rest of Presidents day weekend.
Planning a trip to Chicago? Check out my Chicago guides and itineraries:
