Looking for Chicago Valentine’s Day comedy shows? Whether you’re planning the perfect date, gathering favorite friends, or going solo, the city’s comedy scene will deliver the laughs this Valentine’s Day — and we’ve rounded up 75 shows to help you find your sweet spot. PLEASE confirm all details before leaving home!
AFTERNOON
Beth Stelling Workshop at Lincoln Lodge, 1:00 p.m. A talkback and intimate conversation about comedy and career.
The Paper Machete at The Green Mill, 3:00 p.m. Not-to-be missed comedy experience. And it’s free. Check site for lineup closer to the show. Always excellent. Arriving an hour early is not crazy.
Kid-Prov at BABS Comedy Club, Forest Park, 3:00 p.m. For kids ages 4-12.
Best of the Second City at Second City, 3:00 p.m. Presenting Second City’s classics and classics-to-be.
Early Bird Jam at iO, 3:00 p.m. Free long-form improv jam for students.
The Punch Up at Lincoln Lodge, 4:00 p.m. The Standup Seminary’s graduation show.
Tommy Brennan at Zanies Chicago, 4:00 p.m. Tickets going fast. Still available for Feb. 15 in Rosemont.
The Cosmic Underground Show at Cosmic Underground Theater, 4:30 p.m.
Josh Johnson at The Chicago Theatre, 5:00 p.m. The Flowers Tour. Many shows this week, most sold out, but definitely keep checking in case more are released. (Please follow my 2026 alerts and you’ll always get tickets in time.)
Keep Coming Back at Lincoln Lodge, 5:00 p.m. A variety show about all varieties of recovery.
The Power Couples of Improv 13 at Comedy Clubhouse, 5:30 p.m.
Hot People Island at The Annoyance, 5:30 p.m. An original comedy by Deana Velandra for reality show addicts and haters alike.
Hecklers’ Happy Hour at Lincoln Lodge, 5:45 p.m. Interactive pre-show at 5:45. Show at 6. A different kind of talkback. Heckling encouraged. Crowdwork. See what happens.
NIGHT
Hahas y Jajas at BABS Comedy Club, Forest Park, 6:00 p.m. Uzi Acosta, Jose Alfredo, Adrian Ayala, and Dave Ramos host this monthly showcase en español y spanglish.
Greg Warren at Zanies Rosemont, 6:00 p.m. & 8:30 p.m. The Impulse Buy Tour.
Best of iO Improv at iO, 6:00 p.m. Teams perform celebrated iO forms and in between, unique crowd work.
Comedy Sportz at iO, 6:00 p.m. & 8:00 p.m. Chicago’s classic longest-running comedy game show. Appropriate for all ages 8-80.
Dad’s Records Presents Saturday Supper at iO, 6:00 p.m. Standup, Harold and a slot devoted to chaos.
Beginners’ Grad Show at Lincoln Lodge, 6:00 p.m.
Standup Throw Down Millenials vs. Gen X at Second City, 7:00 p.m. Todd Glover’s hit show.
Jessica Kirson at The Riviera, 7:00 p.m. Very few tickets left. I’m addicted to her reels.
Valentine’s Day Comedy at The Auditorium Theater, 7:00 p.m. Sheryl Underwood, Rod Man, George Wilborn, Michael Colyar, J. Anthony Brown. Music by Carmichael Musiclover.
Love is a Joke Comedy Tour at Yellow & Co., Mahomet, IL, 7:00 p.m. With Abbi Crutchfield & Luke Thayer. “We got married so you don’t have to.”
Valen-Wine’s Day at iO, 7:00 p.m. Comedian and wine pairings.
Calvin Evans at Comedy Bar, 7:00 p.m. & 9:00 p.m.
Trigger Happy at The Annoyance, 7:00 p.m. Created by Mick Napier, a unique method of bringing improv alive.
Fab Monroe & John Gasper at Comedy Plex, Oak Park, 7:00 p.m. Special Valentine’s Day show. Also special dinner offer from Ristoronte Sorelle (limited number available).
Limelight at Lincoln Lodge, 7:00 p.m. Showcasing five Chicago comedians.
Francis Ellis at The Comedy Vault, Batavia, 7:00 p.m. & 9:30 p.m. Early show already sold out.
Clued In at Second City, 7:00 p.m. A mystery unfolds. A new show every time.
Wow, You’re Actually Funny at Surge Billiards, 7:00 p.m. Headliner Ray Roberts with Jon Moore, Morgan Leigh, Andrew Neylon, Rachel Dispenza, Molly McGuire. Plus a trivia challenge. Show by Marcus Cirino.
This Too Shall Slap at Second City, 7:00 p.m. The 113th Mainstage Revue.
Second City’s Improv Supernova at Second City, 7:00 p.m. The e.t.c.’s 50th Revue.
Marvin Phipps at Culture Connects 707, Evanston, 7:30 p.m. A Valentine’s Day date night comedy show. With Comedian Famo.
Russell Peters at The Improv, Schaumburg, 7:00 p.m. & 9:30 p.m. Waitlist only. Follow link for more dates.
Emilio Morrone hosts Vivian Burgett, Brandon Kieffer & headliner Em Brown at Salernos Pizza, Oak Park. Dinner at 7. Show at 8.
Tommy Brennan at Zanies Chicago, 7:00 p.m. & 9:15 p.m. Tickets going fast. Still available for Feb. 15 at Zanies Rosemont.
David Nihill at The Den Theatre, 7:15 p.m. & 9:30 p.m. The Taking Tangents Tour.
Main Stage Improv Showcase at Comedy Clubhouse, 7:30 p.m.
Cupid’s Comics at Riddles, Alsip, 7:30 p.m.
Riddles on the Road at Hobart Theater, Hobart, IN, 7:00 p.m. & 9:00 p.m. David Pendleton Valentine’s Day special.
Power Point Night Live at Lincoln Lodge, 7:30 p.m. Definitely not your workplace presentation.
My Funny Valentine at Laugh Factory, 7:30 p.m. & 9:30 p.m. Early show: Joe Fernandez, Calvin Evans, Deanna Ortiz, Joe Eames. Late show: Calvin Evans, Noe Noel, Sohrab Forouzesh
Whirled News Tonight at iO, 7:30 p.m. Laugh therapy for the news-weary.
Improvised Jane Austen at iO, 7:30 p.m. A Jane Austen rom-com for our times. PerformInk said “makes running amok look like delicious fun.”
Improvised Shakespeare Chicago at iO, 7:30 p.m. Witness the birth of a brand new Shakespeare comedy.
Pigskin The Musical at The Annoyance, 7:30 p.m. “Raunchy highs and tragic lows of high school football.”
Laugh Your Heart Out at Quail Meadows, Washington, IL, 8:00 p.m. From the creators of Bad Momz of Comedy!
Josh Johnson at The Chicago Theatre, 8:00 p.m. The Flowers Tour.
Beth Stelling & Friends at Lincoln Lodge, 8:00 p.m. Standup from Beth Stelling and favorite comedy friends. Tickets selling fast.
Mortified at Lincoln Hall, 8:00 p.m. The Annual Doomed Valentines Show.
Best of the Second City at Second City, 8:00 p.m.
The Kitty & Kelly Show at Second City, 8:00 p.m. For the Galentines.
Joy Gamby at Red Room Comedy, 8:00 p.m. With host Demitri Venice and Evelyn Troutman, Addison O’Neal, Sepehr Vakil.
Dine, Laugh, Love at BABS Comedy Club, Forest Park, 8:00 p.m. A comedy variety show and buffet from Yum Thai.
George Lopez at The Genesee Theatre, Waukegan, 8:00 p.m.
Brandon Vestal at CG’s Comedy Club, Bolingbrook, 8:00 p.m.
Fire & Beer at The Annoyance, 8:00 p.m. The Annoyance House Ensemble looks at the darker side of life & relationships. Valentine’s catharsis!
Funny Valentine at iO, 8:00 p.m. Comedy burlesque.
Chill AF Presents at Second City, 8:30 p.m. Chicago’s great standups plus surprise drop-ins.
Baby Wants Candy at Second City, 8:30 p.m. Completely improvised full-band internationally touring musical.
Riff City at iO, 9:15 p.m. Show at 9:30, but arrive early to have a say in the show.
Naughty Nite Laughs at Comedy Plex, Oak Park, 9:30 p.m. Pares Ratliff hosts this curated R-rated showcase.
D.A.R.E. Dropouts Presents After School Special at iO, 9:30 p.m. iO’s first all-POC house team.
Best of Annoyance Sketch at The Annoyance, 9:30 p.m.
Tricky Micky & Friends at Comedy Clubhouse, 9:30 p.m. Fast-paced two-person improv.
LATE NIGHT
Cupid’s Comics at Riddles, Alsip, 10:00 p.m.
PhonZy|My Life at Red Room Comedy Club, 10:00 p.m.
This Too Shall Slap at Second City, 10:00 p.m. The 113th Mainstage Revue.
Second City’s Improv Supernova at Second City, 10:00 p.m. The e.t.c.’s 50th revue.
After Hours with Calvin Evans at Zanies Chicago, 11:15 p.m.
Harolds After Dark at iO, 11:00 p.m. New and upcoming teams.
First Date Comedy Game Show at Laugh Factory, 11:30 p.m. With Kieron Harrell and Tiny Thickemz.
We Took Edibles an Hour Ago at The Annoyance, 11:59 p.m.