Valentine’s Day 2025: Fifty-five Shows!

I haven’t done one of these in a while. Doesn’t it seem harder to laugh lately? ALL THE MORE reason to celebrate Valentine’s Day at one of Chicago’s signature comedy venues. If laughter is the shortest distance between two people (Victor Borge), then prioritize punchlines over pick-up lines, and let go and let laugh. You deserve it! Keep the laughter going longer if you can. I’ve double-checked all these links and details, but please confirm before leaving home. Looking for shows for the rest of 2025? Here’s a big list of ticket alerts in progress.

FRIDAY, FEBRUARY 14

Kristen Toomey at Comedy Plex, Oak Park, 8:00 p.m. An internationally touring headliner with literally millions of online views known for her honesty and original take on every topic. Her debut album Mother. Fucker. was #1 on iTunes. Use code 2FORTOOMEY for two for one tickets

Lip Service at Lincoln Lodge, 7:00 p.m. Fem Com graduates April Granato, Kathleen Maus, Susie Shipley, Angela Zoiss, Gillian Kerns, Annie Swank.

Braided at Lincoln Lodge, 7:30 p.m. Three comedians weave in and out of each other’s sets.

The Lincoln Lodge Comedy Showcase 8:00 p.m. The nation’s longest running independent stand-up comedy showcase. Really? Yes! Read Mike Bridenstine’s most excellent book The Perfect Amount of Wrong.

Demon Hour at Lincoln Lodge, 9:00 p.m. “Chicago’s raw and untamed confessions.”

Laughter Hours at Lincoln Lodge, 11:00 p.m. Comedy and jazz.

The F U Comedy Showcase at Lincoln Lodge, 9:30 p.m. Christian Royce, Aaron Chase, & Adam Kwaselow with maybe the city’s raunchiest showcase.

Blackout Diaries at Lincoln Lodge, 10:00 p.m.  “Standup comedians, plus ‘regular’ people tell incredible true drinking stories.” Soon to be a TV pilot. Follow Sean Flannery for details.

Joey Villagomez at CG’s Comedy Club, Bolingbrook, 8:00 p.m. A sought after headliner nationwide. Featured on the New Latin Kings of Comedy Tour.

Marlon Wayans at Hard Rock Casino, Rockford, 7:00 p.m. His films have earned over a billion dollars worldwide and of course he can be seen on big and small screens everywhere. A rare opportunity to see Marlon Wayans in person. Very few tickets left.

Taylor Tomlinson at The Chicago Theatre, 7:00 p.m. The award-winning After Midnight host is here Feb. 12-15. You might have better luck finding tickets Wednesday (Feb. 12) or Thursday (Feb. 13).

B-Phlat at Riddles, Alsip, 7:30 & 10 p.m. B-Phlat a/k/a Beverly Nelson is known as an especially empowering voice for women and very funny for everybody. She had a successful business career at Philadelphia’s largest law firm before getting up one night at an open mic. Since then, she has appeared on TV, written for ESPN, and headlined comedy tours across the country.

Meet Cute at The Den Theatre, 7:00 p.m. Tonight this comedy dating show focuses on GenZ.

My Funny Valentine at Laugh Factory, 7:00 p.m. Early show with Vic Pandya, Stephanie Robertson, Rodney Lumpkins, Mike Samp, Jayson Acevedo, Josh Ocean Thomas.

My Funny Valentine at Laugh Factory, 9:15 p.m. Late show with Marcella Arguello, Rodney Lumpkins, Mike Samp, Deana Ortiz, Lyssa Laird, St James Jackson, Clay Season, Sarah Perry

Matthew Broussard at The Comedy Vault, Batavia, 7:00 & 9:30 p.m. He has performed all over TV as a comedian and actor. Despite his self-effacing ways (“disgraced financial analyst forced into standup”) is one of the funniest people around.

My Funny Valentine at Laugh Factory, 11:30 p.m. Latest show. Rodney Lumpkins, Mike Samp, Marcella Arguello, Sarah Perry.

The Punch Bowl at The Den Theatre, 9:00 p.m. Distinctly Chicago sketch.

Yannis Pappas at The Den Theatre, 7:15 p.m. This former social worker is now an internationally touring headliner with multiple hit podcasts.

Onward and Out of Your League at Second City Black Box Cabaret, 7:30 p.m. A special Valentine’s Day edition. A comedic lens on “the perils of dating and loneliness and the general overwhelming feelings that confront us every day.”

Prov Ur Love 2 Me at Second City Black Box Cabaret, 9:00 p.m. An improvised dating show.

We Always Bounce Black at Second City UP Comedy Club, 8:00 p.m. A Black Excellence comedy revue.

Standup Throw Down at Second City Judy’s Beat Lounge, 7:00 p.m. Hosted by Todd Glover. Millenials vs. Generation X comedy battle. Tickets sell out fast!

The Devil is in the Detours at Second City, 7:00 & 10:00 p.m. The 112th Mainstage Revue.

Best Kept Secret… Tell Everyone at Second City e.t.c. Theater, 7:00 & 10:00 p.m. An interactive comedy speakeasy.

Clued In at Second City Donny’s Skybox, 7:00 p.m. An improvised murder mystery.

Shamilton at Second City Donny’s Skybox Theater, 8:30 p.m. An improvised hip hop musical.

Improvised Sitcom at Second City Judy’s Beat Lounge, 8:30 p.m. Completely made up on the spot.

Coached Ensembles at Second City Donny’s Skybox Theater, 7:30 p.m. With $15 tickets, Second City’s most economical option tonight.

Sam Tallent at Zanies Rosemont, 7:15 & 9:30 p.m. Internationally touring headliner, novelist and host of the Chubby Behemoth Podcast.

Charlie Berens at Zanies Chicago, 7:00 & 9:15 p.m. He’s also a New York Times bestselling author, Emmy-winning journalist, musician and creator of the Manitowoc Minute. Sold out, but always worth calling to check if it’s possible to get in.

Lucy’s Comedy at The Raue Center, Crystal Lake, 8:30 p.m. Ted Willson hosts Catherine Strauss, Tricia Babischkin & headliner Maggie DePalo.

Bret Ernst with Paul Farahvar at The Improv, 7:00 & 9:15 p.m. One of Variety‘s Top Five comics to watch and Cousin Louie LaRusso on the Netflix hit Cobra Kai, among many other TV appearances.

Chris Bader at The Comedy Bar, 7:00 & 9:00 p.m. A Chicago favorite and popular performer at comedy festivals and clubs nationwide. Chris has a lot to say about relationships and growing up in an Iranian-American family.

My Funny Valentine at Teatro ZinZanni, Cambria Hotel, 7:00 p.m. Love, chaos & dinner.

Valentine’s Night Out at Klein Creek Golf Club, Winfield, 7:00 p.m. Dinner, chocolate & wine-tasting and comedy by Jay Harris. Mike Stricker opens.

Love Seat at iO, 9:30 p.m. Improv inspired by audience members’ real love story.

Comedy Sportz at iO, 7:00 p.m. Chicago’s longest running short-form improv show.

Devil’s Daughter at iO, 7:30 p.m. Nationally touring improv team.

Improvised Shakespeare at iO, 7:30 p.m. A freshly wrought Shakespearean marvel doth unfold ere thine very eyes.

Kohl’s Cash (TGIF) at iO, 9:30 p.m. “That’s Good Improv Friday”

Best of the Spades Table at iO, 7:30 p.m. What happens at the table doesn’t stay at the table.

Trapped in a Musical at iO, 9:00 p.m. A Malarkey Presentation.

Voila! at iO, 9:30 p.m. A polished yet made up musical.

Mortified Live at The Athenaeum, 8:00 p.m. “Love hurts.”

Main Stage Improv Showcase at The Comedy Clubhouse, 7:30 & 9:30 p.m. Presented by the house teams.

NO LOVE Pop Up Comedy Show at Red Room, 8:00 p.m. Kathryn Gongaware hosts Claire Sundbye, Kieron Harrell, Michael Meyers, Jeff Brumfield.

Blank! The Musical at The Revival, 7:00 p.m. An audience interactive musical.

Chicago Style Improv at The Revival, 9:00 p.m. Come see classic high energy classic Chicago improv.

Live Laugh Blood at The Annoyance, 8:00 p.m. “Lesbian romcom with axe murder.”

Missed Call at The Annoyance, 8:00 p.m. A new sketch show every Friday.

Escapades! at The Annoyance, 9:30 p.m. Choose your own adventure sketch.

Hitch*Cocktails at The Annoyance, 10:00 p.m. Alcohol Hitchcomedy.

Riff City at The Annoyance, 10:30 p.m. An evening of riffing with the audience, so a new original show every time.

Holy Fuck Comedy Hour at The Annoyance, 11:59 p.m. An eclectic show and one of the city’s longest-running most famous late night comedy destinations.