February in Chicago is anything but quiet. From honoring the city’s pivotal role in Black History Month to indulging in Restaurant Week’s final weekend, catching a comedy show, or lacing up for a Valentine’s Day fun run — there’s something for everyone this month.
Here’s your curated guide to the best things to do in Chicago in February 2026.
✊ BLACK HISTORY MONTH
February is Black History Month — and it all started right here in Chicago.
In 1926, historian Carter G. Woodson and the Association for the Study of Negro Life and History launched “Negro History Week” from the South Side, choosing February to honor the birthdays of Abraham Lincoln and Frederick Douglass. A century later, Chicago continues to lead the celebration.
Chicago Public Library’s 2026 Theme: “From Archives to Innovation: The Power of Black Librarianship”
Film Screenings
“Jazz on a Summer’s Day”
📍 Harold Washington Library Center
🕚 Friday, February 6, 2026
🎟️ FREE | chipublib.org
“Fences”
📍 West Chicago Avenue Branch
🕚 Sunday, February 8, 2026
🎟️ FREE | chipublib.org
“Faubourg Tremé”
📍 Harold Washington Library Center
🕚 Friday, February 13, 2026
🎟️ FREE | chipublib.org
Ida B. Wells Documentary
📍 Whitney M. Young Jr. Branch
🕚 Tuesday, February 17, 2026
🎟️ FREE | chipublib.org
“Tell Them We Are Rising”
📍 Harold Washington Library Center
🕚 Friday, February 27, 2026
🎟️ FREE | chipublib.org
Special Programs & Workshops
Musical Lunch with Windy Indie
📍 Harold Washington Library Center
🕚 Wednesday, February 4, 2026 (lunchtime)
🎟️ FREE | chipublib.org
Musical Lunch with Windy Indie
📍 Harold Washington Library Center
🕚 Wednesday, February 25, 2026 (lunchtime)
🎟️ FREE | chipublib.org
🍽️ RESTAURANT WEEK
Chicago Restaurant Week- Final Weekend!
📍 470+ restaurants citywide
🕚 January 23 – February 8, 2026
🎟️ Lunch/Brunch $30 | Dinner $45-$60 | No tickets needed, reservations recommended | choosechicago.com/chicago-restaurant-week
🎭 THEATER WEEK
Chicago Theatre Week
📍 Theaters citywide
🕚 February 5–15, 2026
🎟️ Discounted tickets | chicagotheatreweek.com
Dance of Death
📍 Mercury Theater, 3745 N Southport Ave, Lakeview
🕚 Throughout February (evening performances)
🎟️ Varies | mercurytheaterchicago.com | 773-325-1700
😂 COMEDY SHOWS
Matthew Broussard
📍 The Den Theatre, Wicker Park
🕚 February 6–7, 2026
🎟️ Varies | thedentheatre.com
Josh Johnson: The Flower Tour
📍 The Chicago Theatre
🕚 February 14–15, 2026
🎟️ Varies | msg.com/chicago-theatre
Second City (Ongoing Throughout February)
“It’s Hard to Be Hot”
📍 Second City Mainstage/UP Comedy Club
🕚 Various showtimes throughout February
🎟️ Varies | secondcity.com/shows/chicago
The Black Excellence Revue
📍 Second City Chicago Mainstage
🕚 Various showtimes throughout February
🎟️ Varies | secondcity.com
🏃 FUN RUNS & RACES
Lunar New Year Run 5K/10K/13.1
📍 Chicago/Evanston
🕚 Saturday, February 7, 2026 (morning start)
🎟️ Registration required | runguides.com/chicago
Miles Per Hour Run
📍 McCormick Place
🕚 Sunday, February 8, 2026 (morning)
🎟️ Registration required | cararuns.org
Run for Chocolate 5K/10K/13.1
📍 Chicago/Evanston
🕚 Saturday, February 14, 2026 (morning start)
🎟️ Registration required | runsignup.com
Valentine’s Day Spirits Run 5K
📍 Chicago
🕚 Saturday, February 14, 2026 (morning)
🎟️ Registration required | runguides.com/chicago
🏈 SUPER BOWL WATCH PARTIES
Gracie O’Malley’s Portage Park
📍 4058 N Milwaukee Ave
🕚 Sunday, February 8, 2026 (game time)
🎟️ No cover | gracieomalleyschicago.com
❤️ VALENTINE’S DAY
Eataly Valentine’s Festa
📍 Eataly Chicago
🕚 Friday, February 13, 2026 | 6–8 PM
🎟️ Tickets required | eataly.com
Ballroom Dance Chicago Valentine’s Day Ball
📍 4039B N Ravenswood Ave
🕚 Saturday, February 14, 2026 | 7:30–10 PM
🎟️ $199/couple (BYOB, 21+, limited to 30 couples) | ballroomdancechicago.com
Valentine (Horror Film Screening)
📍 Music Box Theatre, 3733 N Southport Ave
🕚 Saturday, February 14, 2026 (check showtimes)
🎟️ General admission | musicboxtheatre.com
Get my Galentine’s and Valentine’s Day Guide
🎬 MUSIC BOX THEATRE SCREENINGS
The Princess Bride
📍 Music Box Theatre, 3733 N Southport Ave
🕚 February 2026 (various showtimes)
🎟️ General admission | musicboxtheatre.com
Working Girl: The Films of Barbara Stanwyck
📍 Music Box Theatre, 3733 N Southport Ave
🕚 February 2026 (various showtimes)
🎟️ General admission | musicboxtheatre.com
Joe Dirt
📍 Music Box Theatre, 3733 N Southport Ave
🕚 February 2026 (various showtimes)
🎟️ General admission | musicboxtheatre.com
❄️ POLAR ADVENTURE DAYS
Polar Adventure Day at Big Marsh Park
📍 Big Marsh Park, 11559 S. Stony Island Dr
🕚 Saturday, February 21, 2026 | 11 AM – 3 PM
🎟️ FREE (parking fees may apply) | Husky sled dog demos, ice sculpting, puppet shows, live music, art activities, nature play, live reptiles & birds, Shedd Aquarium educators, bonfires, hot cocoa | Sponsored by Ford Motor Company | chicagoparkdistrict.com
🛒 MARKETS
Wicker Park Winter Farmers Market
📍 Royal Palms Shuffleboard Club
🕚 Sundays in February | 10 AM – 2 PM
🎟️ FREE admission | royalpalmschicago.com
Plan Your February in Chicago
February may be cold, but Chicago’s event calendar is red hot. Whether you’re celebrating Black History Month, catching a show during Theatre Week, or running through the city on Valentine’s Day, there’s no shortage of ways to embrace the season.
Which event are you most excited about? Drop a comment below or tag me on Instagram @maureenmoran.realtor — I’d love to hear what you’re planning!
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If you would like to have an event featured, email Maureen at mmoran@atproperties.com
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