📅 This Week in Chicago Comedy

10–14-2026 Sam Dicke and Friends

Second City Chicago Mainstage · 8:00 PM · Sketch

Free

Schubas Tavern · 8:00 PM · Stand-Up

Sam Dicke

Free

Hush Hush Stand Up Comedy Show

The Lincoln Lodge · 8:00 PM · Variety

$12.83+

FREE Open Mic Comedy and Tre Sorrelle Coffee

Comedy Plex Comedy Club · 8:00 PM · Open Mic

Free

Wednesday Night Stand Up Comedy at Laugh Factory Chicago

Laugh Factory Chicago · 8:00 PM · Stand-Up

$21.41+

Comedians You Should Know: Chicago's Funniest Stand-Up. No Joke.

Timothy O'Toole's Pub Chicago · 8:00 PM · Stand-Up

$17.55+

Green Room - An Improv Jam

Second City Chicago Mainstage · 8:00 PM · Sketch

$40+

iO Theater · 9:00 PM · Improv

Free

The Freaks Come Out at Night: Hollyween Season 4

Second City Donny's Skybox Theater - Chicago · 9:00 PM · Sketch

$20+

The Fizz Show: Carbonated Chicago Comedy

iO Theater · 9:00 PM · Improv

$12+

Jury Duty

Annoyance Theatre · 9:30 PM · Improv

Free

Comedy Open Mic with Easy Laughs

Easy Bar · 10:00 PM · Open Mic

Free

Cage Match

iO Theater · 10:00 PM · Improv

Cage Match

$12+

Thursday, October 1533 shows

Chicago Comedy Club

Foundation Room at House of Blues Chicago · 6:30 PM · Stand-Up

Free

Chrissa Sparkles: “DELULU” (Theatre 2A)

The Den Theatre · 7:00 PM · Stand-Up

Chrissa Sparkles

Free

Joe Dombrowski (Heath Mainstage)

The Den Theatre · 7:00 PM · Stand-Up

Joe Dombrowski

Free

Improvised Animorphs

Stars and Garters Theater · 7:00 PM · Stand-Up

Improvised Animorphs

$25.5+

Damitas Histeria (En Español)

Chicago Improv · 7:00 PM · Stand-Up

Damitas Histeria

$59.1+

Lowkey Lit

Second City Judy's Beat Lounge - Chicago · 7:00 PM · Sketch

$20+

A Dreadful...

iO Theater · 7:00 PM · Improv

$20+

Zanies Presents HaHas for Tatas

Zanies Comedy Club Rosemont · 7:00 PM · Stand-Up

Zanies Presents

Free

4000 Miles (The Crosby)

The Den Theatre · 7:30 PM · Stand-Up

Free

Pee-Wee's Gayhouse

Stars and Garters Theater · 7:30 PM · Stand-Up

Pee-wee's Gayhouse

$25.5+

I'm Gonna Marry You Tobey Maguire (The Bookspan)

The Den Theatre · 7:30 PM · Stand-Up

Free

Clued In Presents: Travel Can Be Murder

Second City UP Comedy Club - Chicago · 7:30 PM · Sketch

Clued In Presents

$30+

Set In Chicago - Improvised Spooky Movie Sequels

Second City de Maat Studio Theatre - Chicago · 7:30 PM · Sketch

$20+

Improv: The Play

iO Theater · 7:30 PM · Improv

Free

Thursday Night Improv with Creamboy

iO Theater · 7:30 PM · Improv

$7.5+

The Thursday Show

Logan Square Improv · 7:30 PM · Improv

$7.18+

Chicago Comedy Club at the House of Blues! Chicago's BEST Comedy Show!

House of Blues Chicago · 7:30 PM · Variety

$16.95+

Thursday Night Stand Up Comedy at Laugh Factory Chicago

Second City Chicago Mainstage · 8:00 PM · Sketch

Free

Schubas Open Mic

Schubas Tavern · 8:00 PM · Open Mic

Free

Laugh Factory Chicago · 8:00 PM · Stand-Up

$21.41+

e.t.c. Reality Detox: The Improv Experience

Second City Chicago Mainstage · 8:00 PM · Sketch

$40+

Second City e.t.c. Theater - Chicago · 8:00 PM · Sketch

Reality Detox

$19.59+

East of LA: A Midwest Asian Comedy Show

The Lincoln Lodge · 8:00 PM · Stand-Up

$12.83+

Give It To Me Gay!

Second City Judy's Beat Lounge - Chicago · 8:30 PM · Sketch

$20+

Fellowship Thursdays

Second City Donny's Skybox Theater - Chicago · 8:30 PM · Sketch

Fellowship Thursdays

$1+

Indie City

iO Theater · 9:00 PM · Improv

Indie City

$10+

The Call It A Night Show

Second City de Maat Studio Theatre - Chicago · 9:00 PM · Sketch

$15+

My Buddy's Live! Free Comedy Show Every Thursday at 10pm

My Buddy's · 9:30 PM · Variety

Free

Revolving Door

Annoyance Theatre · 9:30 PM · Improv

Free

Silly Stories to Tell in the Spotlight

iO Theater · 9:30 PM · Improv

$19+

Roast Battle

Zanies Comedy Club Chicago · 9:30 PM · Stand-Up

Roast Battle

$32+

Sketch Playlist

iO Theater · 9:30 PM · Sketch

Free

Blueprint

iO Theater · 10:00 PM · Improv

$10+

Friday, October 1653 shows

Don't Tell Comedy — Chicago - Portage Park

Don't Tell Comedy — Chicago - Portage Park · 3:00 PM · Stand-Up

$28+

Don't Tell Comedy — Chicago - Lakeview

Don't Tell Comedy — Chicago - Lakeview · 3:00 PM · Stand-Up

$28+

iO House Team Night

iO Theater · 6:00 PM · Improv

$5+

Second City Chicago Mainstage · 6:30 PM · Sketch

Free

Second City Chicago Mainstage · 6:30 PM · Sketch

$50+

Chicago Improv · 7:00 PM · Stand-Up

$33.34+

The Comedy Bar - Chicago Main Stage · 7:00 PM · Stand-Up

Friday Night Stand Up Comedy at Laugh Factory Chicago

$33.64+

Buena Onda Comedy

The Lincoln Lodge · 7:00 PM · Variety

$14.89+

Dada Reinvents The Wheel

Stars and Garters Theater · 7:00 PM · Stand-Up

$25.5+

Hags

Stars and Garters Theater · 7:00 PM · Stand-Up

$25.5+

ComedySportz

iO Theater · 7:00 PM · Improv

Free

Laugh Factory Chicago · 7:00 PM · Stand-Up

$29.51+

e.t.c. Reality Detox: The Improv Experience

Second City e.t.c. Theater - Chicago · 7:00 PM · Sketch

Reality Detox

$39+

Joe Dombrowski (Heath Mainstage)

The Den Theatre · 7:00 PM · Stand-Up

Joe Dombrowski

Free

Oh Great, They're Gonna Sing. (Theatre 2A)

The Den Theatre · 7:00 PM · Stand-Up

Free

ANARCHY: The Improvised Rock Opera

Second City Donny's Skybox Theater - Chicago · 7:00 PM · Sketch

$25+

Chicago Improv · 7:00 PM · Stand-Up

Good: A Standup Comedy Showcase

$29.29+

The Lincoln Lodge · 7:30 PM · Stand-Up

$14.89+

Devil's Daughter

iO Theater · 7:30 PM · Improv

Free

4000 Miles (The Crosby)

The Den Theatre · 7:30 PM · Stand-Up

Free

I'm Gonna Marry You Tobey Maguire (The Bookspan)

The Den Theatre · 7:30 PM · Stand-Up

Free

Randomness at a Moment in Time (Upstairs Mainstage)

The Den Theatre · 7:30 PM · Stand-Up

Free

Brad Williams: The Tall Tales Tour

The Chicago Theatre · 7:30 PM · Stand-Up

Brad Williams

Free

DARK and STORMY Comedy Show

Red Room Comedy Club · 7:30 PM · Variety

$15+

Trilogy of Terror

iO Theater · 7:30 PM · Improv

$20+

Improvised Shakespeare Chicago

iO Theater · 7:30 PM · Musical Improv

Free

Feast A Da Funny

George Van Dusen Theatre at North Shore Center · 8:00 PM · Stand-Up

Bret Ernst, Pat Tomasulo, The Good +1 more

Free

Missed Call

Annoyance Theatre · 8:00 PM · Improv

Free

The Lincoln Lodge Comedy Showcase

The Lincoln Lodge · 8:00 PM · Variety

$18.48+

Headliner Series

Zanies Comedy Club Rosemont · 8:00 PM · Stand-Up

Headliner Series

$26+

Best of The Second City

Second City Chicago Mainstage · 8:00 PM · Sketch

$45+

Shamilton

Second City Donny's Skybox Theater - Chicago · 8:30 PM · Sketch

Baby Wants Candy

$25+

M.A.S.T.E.R.M.I.N.D.S.

Stars and Garters Theater · 9:00 PM · Stand-Up

$13.76+

Chicago's Best Comedy Show

The Comedy Bar - Chicago Main Stage · 9:00 PM · Variety

Free

Friday Night Fever Comedy Showcase

The Lincoln Lodge · 9:00 PM · Variety

$18.48+

Honk!

iO Theater · 9:00 PM · Improv

Free

Friday Night Stand Up Comedy at Laugh Factory Chicago

Laugh Factory Chicago · 9:15 PM · Stand-Up

$29.51+

Chicago Improv · 9:15 PM · Stand-Up

Reverse Therapy: A Stand-Up Comedy Show

$29.29+

iO Theater · 9:30 PM · Stand-Up

Reverse Therapy

$15+

Improvised Survivor: Abridged

iO Theater · 9:30 PM · Improv

$15+

Chicago Improv · 9:30 PM · Stand-Up

$33.34+

Hitch*Cocktails

Annoyance Theatre · 9:30 PM · Improv

Free

Kohl's Cash: TGIF (That's Good Improv Fridays)

Second City Chicago Mainstage · 9:30 PM · Sketch

Free

iO Theater · 9:30 PM · Improv

$12+

e.t.c. Reality Detox: The Improv Experience

Second City Chicago Mainstage · 9:30 PM · Sketch

$45+

Second City e.t.c. Theater - Chicago · 9:30 PM · Sketch

Reality Detox

$39+

Laugh Now Cry Later

The Lincoln Lodge · 9:30 PM · Stand-Up

$12.83+

Riff City Standup Comedy Show

The Lincoln Lodge · 10:00 PM · Stand-Up

$18.48+

Blackout Diaries

The Lincoln Lodge · 10:00 PM · Variety

$18.48+

Laughter Hours: Late Night Jazzy-Themed Comedy Show

The Lincoln Lodge · 11:00 PM · Variety

$14.89+

The 11pm Show

iO Theater · 11:00 PM · Improv

$5+

Friday Night Stand Up Comedy at Laugh Factory Chicago

Laugh Factory Chicago · 11:30 PM · Stand-Up

$21.41+

Holy Fuck Comedy Hour

Annoyance Theatre · 11:59 PM · Improv

Free

Saturday, October 1733 shows

Blood Drive: The Show

iO Theater · 11:30 AM · Improv

Blood Drive

$10+

Bright Star Circus

Stars and Garters Theater · 12:00 PM · Stand-Up

Bright Star Circus

$25.5+

Comedy Brunch! Featuring Bad Momz of Comedy

The Comedy Bar - Chicago Main Stage · 12:00 PM · Stand-Up

$33.64+

The Family Game Show Show

Stars and Garters Theater · 1:00 PM · Variety

$25.5+

No Grown Ups Allowed

Second City Chicago Mainstage · 1:00 PM · Sketch

$29+

Mystery Machine - An Improvised Whodunit

Stars and Garters Theater · 2:00 PM · Stand-Up

Mystery Machine

$25.5+

The Lincoln Lodge · 6:00 PM · Stand-Up

Hecklers’ Happy Hour Comedy Show

$24.37+

The Lincoln Lodge · 6:00 PM · Variety

$12.83+

Second City Chicago Mainstage · 6:30 PM · Sketch

Free

The Séance

Stars and Garters Theater · 7:00 PM · Stand-Up

$48.97+

Chicago Improv · 7:00 PM · Stand-Up

Saturday Night Stand Up Comedy at Laugh Factory Chicago

$33.34+

Ben Schwartz and Friends

The Chicago Theatre · 7:00 PM · Stand-Up

Ben Schwartz

Free

Laugh Factory Chicago · 7:00 PM · Stand-Up

$29.51+

Little Miss Anthropes: All Drag Comedy Showcase

The Lincoln Lodge · 7:00 PM · Variety

$18.48+

Garage Comedy Show

3317 W Belden Ave · 7:00 PM · Variety

$12.51+

Chicago Improv · 7:00 PM · Stand-Up

$29.29+

The Comedy Bar - Chicago Main Stage · 7:00 PM · Stand-Up

“Ask a Comedian” Comedy Show w/ Kyrie Da Comic

$33.64+

Carded

Stars and Garters Theater · 7:30 PM · Stand-Up

$25.5+

The Lincoln Lodge · 7:30 PM · Variety

$18.48+

Red Room Comedy

Red Room Comedy Club · 7:30 PM · Variety

$15+

The Lincoln Lodge Comedy Showcase

The Lincoln Lodge · 8:00 PM · Variety

$18.48+

Sweetest Day Comedy Jam

Wintrust Arena · 8:00 PM · Variety

Cedric The Entertainer, Earthquake, Bruce Bruce +2 more

Free

Prime Time - Chicago's hottest comedy showcase

The Lincoln Lodge · 9:00 PM · Variety

$18.48+

Halloween: Laugh-Along, Live!

Stars and Garters Theater · 9:00 PM · Stand-Up

$25.5+

Chicago's Best Comedy Show

The Comedy Bar - Chicago Main Stage · 9:00 PM · Variety

Free

Saturday Night Stand Up Comedy at Laugh Factory Chicago

Laugh Factory Chicago · 9:15 PM · Stand-Up

$29.51+

Chicago Improv · 9:15 PM · Stand-Up

$29.29+

Chicago Improv · 9:30 PM · Stand-Up

Slumber Party! A Comedy Show for Gossip Lovers

$33.34+

The Lincoln Lodge · 9:30 PM · Variety

$18.48+

Naughty Nite Laughs: Best R-Rated Comedy Showcase in Chicagoland

Second City Chicago Mainstage · 9:30 PM · Sketch

Free

Comedy Plex Comedy Club · 9:30 PM · Variety

Free

The Lincoln Lodge · 9:30 PM · Stand-Up

Saturday Night Stand Up Comedy at Laugh Factory Chicago

$24.37+

Laugh Factory Chicago · 11:30 PM · Stand-Up

$21.41+

Sunday, October 1816 shows

Hot 5 Comedy Show

The Lincoln Lodge · 6:00 PM · Variety

$14.89+

La Mole (En Español)

Chicago Improv · 6:00 PM · Stand-Up

La Mole

$65.53+

Saya Meads at The Lincoln Lodge - 10/18/26 One Night Only!

The Lincoln Lodge · 6:00 PM · Stand-Up

Saya Meads

$30.02+

FALL BREAK | Comedy Showcase

Red Room Comedy Club · 6:00 PM · Variety

Fall Break

$15+

FOOS GONE WILD: The FOOS GONE WILD Tour 2026

House of Blues Chicago · 6:30 PM · Stand-Up

Foos Gone Wild

Free

Sautéed Standup: Chicago's Only Live Comedy Cooking Competition Show!

Second City Chicago Mainstage · 7:00 PM · Sketch

Free

Calimar White

The Comedy Bar - Chicago Main Stage · 7:00 PM · Stand-Up

Calimar White

$39.87+

The Lincoln Lodge · 7:00 PM · Variety

$18.48+

Sunday Night Stand Up Comedy at Laugh Factory Chicago

Laugh Factory Chicago · 7:00 PM · Stand-Up

$21.41+

Sunday Best

The Lincoln Lodge · 7:30 PM · Stand-Up

$12.83+

The Incredibly Serious Stand Up Hour

Stars and Garters Theater · 7:30 PM · Stand-Up

$25.5+

Dyke Country

The Lincoln Lodge · 8:00 PM · Stand-Up

Dyke Country

$12.83+

The Sunday Show (ft. The Late 90s)

Logan Square Improv · 8:00 PM · Improv

$6.94+

Marti and Mimi's "Back to School" Charity Ball

Stars and Garters Theater · 8:30 PM · Stand-Up

$19.64+

Fred Armisen: Comedy For Musicians But Everyone Is Welcome

Cahn Auditorium · 8:30 PM · Variety

Fred Armisen

Free

Sunday Night Stand Up Comedy at Laugh Factory Chicago

Laugh Factory Chicago · 9:00 PM · Stand-Up

$21.41+

Monday, October 195 shows

Late Nite Mic with Vik Pandya

The Comedy Bar - Chicago Main Stage · 7:00 PM · Stand-Up

Vik Pandya

$29.9+

Laughs in Lakeview Stand-Up Comedy Showcase/OpenMic

Shaker's on Clark · 8:00 PM · Open Mic

Free

Open Mic Night

The Comedy Vault · 8:00 PM · Open Mic

Free

Monday Night Stand Up Comedy at Laugh Factory Chicago

Laugh Factory Chicago · 8:00 PM · Stand-Up

$21.41+

Jokes on Division Stand Up Comedy Showcase

Butch McGuire's · 9:00 PM · Stand-Up

Free

Tuesday, October 208 shows

Read the Room: A Literary Competition Comedy Show

The Lincoln Lodge · 7:00 PM · Variety

$12.83+

Tomato Throw Show

The Comedy Bar - Chicago Main Stage · 7:00 PM · Stand-Up

$29.9+

Tuesday Night Stand Up Comedy at Laugh Factory Chicago

Laugh Factory Chicago · 7:30 PM · Stand-Up

$14.12+