Searching for what to do this weekend in Chicago? Below are the best things to do in Chicago this weekend (February 21-23, 2025).
(If you are planning ahead, you can also find the best things to do next weekend here.)
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.
Best Weekend Events in Chicago
Below are the best weekend events in Chicago:
Music Frozen Dancing – Saturday, February 22, 2025, 1pm until dark – Annual winter block party outside Empty Bottle on Cortez
MagicCon: Chicago – February 21-23, 2025
Unicorn World (Rosemont) – February 22-23, 2025
The Inaugural West Loop Contemporary Fine Art Expo – February, 21-23, 2025 – Curated boutique expo with over 40 invitation-only fine artists offering direct sales to the public.
Andersonville Restaurant Week – February 21-March 2, 2025
Chicago Black Restaurant Week – Through February 23, 2025
Grace O’Malley at The Den Theatre – February 21-22, 2025
Frida…A Self Portrait at Writer’s Theatre – Through February 23, 2025
Chopin In The City – February 21 – March 1, 2025
Chicago’s Original Malort Day at DMen Tap – Friday, February 21, 2025, 2pm
Cupid’s Undie Run – Saturday, February 22, 2025
16th Annual Shelter Shiver at North Avenue Beach – Sunday, February 23, 2025, 10am – Polar plunge and after party to raise money for homeless animals of Chicago.
Commemorative Day | Black History Month at the Chicago History Museum – Saturday, February 22, 2025, 10am-2pm – Hands-on arts activities, music, and speakers celebrating Black History Month by looking at the ways art has been a vehicle for social change in Chicago’s African American community.
9th Annual Pulaski Day Pub Crawl at Revolution Brewing – Saturday, February 22, 2025, 10am-5:30pm
Dog Day at the Music Box Theatre – Saturday, February 22, 2025, 1:30-4:00pm
The Newport Peekeasy: Burlesque and Variety Show – Saturday, February 22, 2025, 7:00–8:30pm
Hustle Chicago® Stair Climb – Sunday, February 23, 2025
Queer Eye: Fab Five Live! at the Chicago Theatre – Sunday, February 23, 2025, 7:30pm
More Weekend Events in Chicago
Below are more events taking place this weekend in Chicago:
Third Friday Art Walk at Marz Community Brewing Co. (Bridgeport) – Friday, February 21, 2025, 6-9pm
Zhou B Art Center 3rd Fridays – Friday, February 21, 2025, 7-10pm
Soul Train Gospel Music Revival – In Celebration Of Black History Month – Friday, February 21, 2025, 7:30pm
Second City Onward and Out of Your League – Friday, February 21, 2025, 7:30pm – The Onward cast navigates the perils of dating, loneliness, and the general overwhelming feelings that confront us every day through sketch comedy, improv, and music.
Gamer’s Universe Showdown Series at Harold Washington Library Center – Saturday, February 22, 2025, 11am-4pm | FREE
Black Makers Market at Navy Pier – Saturday, February 22, 2025, 12pm-6pm
‘Love is in the Air’ Adoption Event – Saturday, February 22, 2025, 12–6pm – Meet your perfect furry match at Chicago Animal Care and Control with fee-waived pet adoptions.
Repair Fair at Chicago Tool Library – Saturday, February 22, 2025, 1-4pm | FREE – Community event where you can bring your broken and beloved bikes, clothes, appliances, jewelry, and more and work with repair volunteers to fix them.
Create Your Legacy Workshop hosted by Women’s Live Artist Studio (Navy Pier) – Saturday, February 22, 2025, 1-5pm | FREE
Walk and Talk: Black History Month Celebration at LaBagh Woods – Saturday, February 22, 2025, 10:00-11:30am | FREE but registration required
Polar Adventure Day at Big Marsh – Saturday, February 22, 2025, 11am-3pm | FREE
UMOJA Black History Celebration at Homan Square Community Center Park – Saturday, February 22, 2025, 9am-4pm | FREE
Black Creativity Career Showcase at The Griffin Museum of Science and Industry – Saturday, February 22, 2025, 9:30am -2:30pm
Chicago Bacon Fest (21+) – Saturday, February 22, 2025, 12pm
Old Crow’s Country Day Party: Live Band, Welcome Drink & Shot of Whiskey (21+) – Saturday, February 22, 2025, 12-5pm
Chicago Margarita Crawl on National Margarita Day (21+) – Saturday, February 22, 2025, 4-10pm
The Godfrey Charity Ball – Saturday, February 22, 2025, 8-11pm
Junior Council’s 36th Annual Snowball Gala at Palmer House Chicago (21+) – Saturday, February 22, 2025, 8pm-midnight – Annual event featuring live music from Radio Gaga and DJ Strategy, silent auction, premium open bar, tastings from Chicago restaurants, and an after party to follow at Hubbard Inn. All proceeds directly benefit the Pediatric & Adolescent HIV/AIDS Clinic at Ann & Robert H. Lurie Children’s Hospital of Chicago.
Kodo One Earth Tour at Chicago Symphony Orchestra – Sunday, February 23, 2025, 3pm
CLUE at CIBC Theatre – Through March 2, 2025
Fat Ham in Goodman’s Owen Theatre – Extended through March 9, 2025
More Things to Do in Chicago This Weekend
In addition to the weekend events listed above, below are more of the best things to do in Chicago this weekend:
Love Struck – AirOtic Soirée
Love Struck – AirOtic Soirée is a limited time 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: 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.
Shop at an Indoor Farmers Market
You can find several indoor winter farmers markets in Chicago taking place this weekend:
Green City Market (Avondale) – Saturday, February 22, 2025, 8am–1pm
South Loop Farmers Market – Saturday, February 22, 2025, 9am-1pm
Winter Farmers Market at Water Tower Place – Sunday, February 23, 2025, 12pm-4pm
Spring Flower Show at the Garfield Park Conservatory
See the annual Spring Flower Show, “Rooted in Mystery” at the Garfield Park Conservatory, which explores the different types of roots and the cool stuff they do plus a marvelous display of spring plants, including azaleas, pansies, snapdragons, astilbe, baptisia, hydrangeas, and 26 different varieties of tulips, daffodils, and hyacinths.
Spring Flower Show at the Lincoln Park Conservatory
See the annual Spring Flower Show, “Spectrum of Spring” at the free Lincoln Park Conservatory which highlights the color families of plants and flowers and offers a unique design and color scheme.
Take a Spray Paint ‘n’ Sip Urban Art Workshop
Grab some spray paint and unleash your inner street artist at a Spray Paint ‘n’ Sip Urban Art Workshop. This interactive spray paint workshop will teach you the ins and outs of working with spray paint and other elements of graffiti and street art as you create your own painted mural.
Where: Studio W.I.P. – Uptown, 1047 W Lawrence Ave, Chicago, IL 60640
Cost: $40 per person for adults. Click here to purchase tickets.
Go Outdoor Ice Skating
Many outdoor ice skating rinks in Chicago are closed for the season but you can still go ice skating at the skating ribbon at Maggie Daley Park.
As you can see there are many things to do in #Chicago this weekend. If you are looking for more things to do in the Chicago area, you can find the best things to do in the suburbs here. If you are looking for things to do during the week, you can find more things to do in Chicago in February here.
