Valentine’s Day 2021: online comedy for Chicago and beyond

Chicago comedy in the news:

The Pat Tomasulo Podcast Pat goes behind the scenes of his life and talks about life in these times.

Paul Farahvar and Tristan Triptow have a sweet new Instagram venture.

Improv Nerd with Jimmy Carrane Most recently, Jimmy interviewed Michelle Gilliam, owner and artistic director of Milwaukee’s IMPROVMKE. Also – new online improv classes begin this week!

Cameron Esposito is one of the authors featured in the new anthology Hungry Hearts.

Schitt’s Creek Socially Distanced Pop Up will be at Replay in Lincoln Park through April 1st.

Variety reports that bestselling author Samantha Irby has joined the Sex and the City revival as a writer and co-producer.

Steven Yeun was featured on the cover of The New York Times Sunday magazine last week for his work on the new film Minari. He is also known for his starring role in The Walking Dead. He is an alum of Second City and the sketch comedy group “Stir-Friday Night.”

All shows below are online except for Brian Hicks at Zanies. All times are Central Standard Time. Pretty sure the times are correct, but please recheck the math. Also – did I miss a show? Let me know-I’m glad to add it! Thank you for dropping by! Thank you to the comedy community for persevering in these hard times and being our spiritual essential workers!



Undercover Lover 5:00 p.m. Live dating comedy game show with Ben Gleib.

Sweet and Sour Valentine’s Day Comedy Show 6:00 p.m. With Simone, Al Williams, Joanne Filan, & Naomi Karavani. Presented by Improbable Comedy.

After Hours with Margaret Cho 7:00 p.m. Adults only!

Zanies in Person in Rosemont 7:00 p.m. With headliner Brian Hicks.

Laugh Factory Chicago 7:00 p.m. My Funny Valentine with host Paul Farahvar and Sarah Perry, Clark Jones, Meechie Hall, Alex Dragicevich and more TBA.


Cupid’s Big Day 8:00 p.m. An Annoyance Theatre Valentine’s Day show with The Garden Boys.

Zanies 8:00 p.m. Calvin Evans hosts Pat Tomasulo, Carly Kane, Joe Kilgallon and T-Murph. VIP options gets access to the Zoom Room.


Little Piggy Valentines 9:00 p.m. An Annoyance Theatre musical sketch variety show.

Laugh Factory L.A. 9:00 p.m. CST My Funny Valentine with Iliza Shlesinger, Maz Jobrani, Erica Rhodes, Reedo Brown, Vinnie Fasline and more TBA>


Chocolate Sundaes Comedy 9:00 p.m. Every Sunday!


Be My Quarentine 8:30 p.m. KO Comedy and Sammy Obeid host Qing Oracle, Maggie May and Jeff Zenisek.

Steve Hofstetter Heckles Himself 9:00 p.m. Valentine’s Day Edition.

UnCabaret Zoom Edition #22 9:30 p.m. Beth Lapides hosts Alec Mapa, Julia Sweeney, Jen Kirkman, Justin Sayre, Alex Edelman and Jamie Bridgers sharing “stories, wisdom, rants, songs, commune and a deep dive into this now.” With Mitch Kaplan and his band.

Live Comedy On Zoom 10:00 p.m. With originally-from-Chicago Liza Treyger, and Ian Levy, Chelsea Bearce and Paul Conyers.

KO Comedy 10:15 p.m. Chicagoan Sonal Aggarwal hosts Kayla Esmond, Jack Noll, Vikram Pandya, Alexis Bradby, Ahmed Al-Kadri and Macey Issacs.


Louder Than A Mom 8:00 p.m. Post-Valentine’s Day event. Theme: “This thing called love.”

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