Chutzpah in the Chi

11/10/2025

No Christmas carols, just Channukah Parodies!

Join us Christmas Eve for Christmas Chutzpah Live at Joy District — the Jewish comedy pregame before Matzo Bash. Laugh, schmooze, and then dance the night away. Tickets are only $20 and YES there will be Chinese food.
🎟️ https://www.chutzpahinthechi.com/shows/chutzpah-christmas-2025-at-joy-district

✨ Jewish comics, Joy District drinks, and jokes you can’t tell at Christmas dinner

06/16/2025

ChiTribe Private Trivia Event
📍 Graystone  Tavern
🗓️ June 25 7-9
Register now - there are prizes!

https://www.eventbrite.com/e/june-chitribe-trivia-night-in-lakeview-jew-ish-edition-tickets-1307186121879?aff=oddtdtcreaton

Join ChiTribe's Trivia Night in Lakeview on June 25 7 PM! Ages 21-49. Early bird tickets $10. Register for location. MC: Rebecca Schwab

06/01/2025

🌈 Celebrate Pride Month with a night of unapologetically q***r and hilariously Jewish comedy at Chutzpah Pride — happening Wednesday, June 18 at Uptown Taproom!
🎤 Hosted by Madison Burman (She/Her)
Madison Burman is a born and bred Chicago-based comedian. She has performed at Second City, iO, Blanket Fort, and Lincoln Lodge. A chronic over-sharer, she loves talking about her eccentric family, the toils of dating, and how all Muppets are canonically Jewish.

📍 1325 W Wilson Ave
📅 Doors at 7:00 PM | Show at 7:30 PM
🎟️ $10 advance | $15 day-of
https://www.chutzpahinthechi.com/shows/chutzpah-pride-a-q***r-jewish-comedy-showcase
***rJewishJoy ***rJewishJoy ***rComedy ***rAndJewish

05/30/2025

💿 Y2K aesthetic, Gen Z chaos, and vintage Jewish trauma — Quinn James is what happens when your bat mitzvah playlist becomes sentient.

🌈 Catch them at Chutzpah Pride, Chicago’s only Q***r Jewish Comedy Showcase, on Wednesday, June 18 at Uptown Taproom!
📍1325 W Wilson Ave | Doors 7PM | Show 7:30PM | 🎟️ $10/$15
https://www.chutzpahinthechi.com/shows/chutzpah-pride-a-q***r-jewish-comedy-showcase

Known for their physical comedy and electric stage presence, Quinn (Oy/Vey/They) is a vibe and a half.

Don’t miss Chicago’s only Q***r Jewish comedy show, full of chutzpah.
***rIcon ***rComedyMagic

05/27/2025

🎈 Clown. Comic. Chaos machine. Gabby Gabe Sklan brings the joyful absurdity and fearless storytelling that every Chutzpah Pride lineup needs.

🌈 Don’t miss this Q***r Jewish Comedy Showcase on Wednesday, June 18 at Uptown Taproom (📍1325 W Wilson Ave).
🎟️ $10 advance / $15 day-of | 🕖 Doors 7PM | Show 7:30PM
https://www.chutzpahinthechi.com/shows/chutzpah-pride-a-q***r-jewish-comedy-showcase

From the Bad Boyhavior podcast to Chicago’s top stages, Gabe brings every subject to life with just the right amount of respect… which might be none.

Don’t miss Chicago’s only Q***r Jewish comedy show, full of chutzpah.
***rJewishComedy ***rComics

05/23/2025

🧠 Therapist by day, stand-up queen by night — Delilah Orizaba brings the perfect combo of insight and side-splitting laughter to Chutzpah Pride.

🌈 Join us for a Q***r Jewish Comedy Showcase like no other — Wednesday, June 18 at Uptown Taproom (1325 W Wilson Ave).
⏰ Doors at 7PM | Show at 7:30PM | 🎟️ $10/$15
https://www.chutzpahinthechi.com/shows/chutzpah-pride-a-q***r-jewish-comedy-showcase
She’s a Scorpio sun, Capricorn moon and rising — so yes, the jokes are sharp, grounded, and totally unforgettable.

Don’t miss Chicago’s only Q***r Jewish comedy show, full of chutzpah.
***rComedy

05/21/2025

💁‍♀️ Mom, comedian, and lifelong Chicagoan — Dana Kaye is living proof that you can do it all and be funny as hell.
https://www.chutzpahinthechi.com/shows/chutzpah-pride-a-q***r-jewish-comedy-showcase

🌈 Catch her at Chutzpah Pride — a Q***r Jewish Comedy Showcase on Wednesday, June 18 at Uptown Taproom!
📍1325 W Wilson Ave | Doors at 7PM | Show at 7:30PM
🎟️ $10 advance / $15 day-of


From Laugh Factory to Zanies, Dana’s wit and wisdom light up every stage she steps on.
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Don’t miss Chicago’s only Q***r Jewish comedy show, full of chutzpah.

03/15/2025

🎭 Chutzpah in the Chi: The Post-Purim Production is coming to iO Theatre on March 18—hosted by the one and only Rebecca Joey Schwab

🚪 Doors: 7PM | 🎤 Show: 7:30PM
🎟️ Don’t wait—grab your tickets now! ($20 advance, $25 day of) 👉 https://ci.ovationtix.com/36725/production/1217637?performanceId=11605302

Rebecca is Chicago’s most Jewess comedian, producer of Chutzpah in the Chi, and the mastermind behind top-tier Jewish comedy. She brings Jewish joy and unfiltered hilarity to every stage, all while running ChiTribe and co-producing the Windy City Comedy Festival. Because why do one thing when you can do all the things?

03/12/2025

🔥 Purim is tomorrow!!! Stay happy, it's Adar. Chutzpah in the Chi: The Post-Purim Production is keeping the party going at iO Theatre on March 18!
Introducing our fantastic headliner: Lexi Costantini 🥳🌟

🚪 Doors: 7PM | 🎤 Show: 7:30PM
🎟️ Secure your spot now! ($20 advance, $25 day of) 👉 https://ci.ovationtix.com/36725/production/1217637?performanceId=11605302

Time to meet —she’s a one-woman show, a Double D cup, and a triple threat. From stand-up to burlesque, improv to musical comedy, Lexi has done it all. She even made her mark in the New Orleans and Texas comedy scenes! Catch her live in Chicago before she takes over the world.

03/11/2025

🎤 Ready for more unfiltered chutzpah? Chutzpah in the Chi: The Post-Purim Production is hitting iO Theatre on March 18!
Featuring Chicago's FINEST Nice Jewish Boy: Noah Wolf
🚪 Doors: 7PM | 🎭 Show: 7:30PM
🎟️ Tickets are selling fast! ($20 advance, $25 day of) 👉 https://ci.ovationtix.com/36725/production/1217637?performanceId=11605302

Meet Noah Wolf , a Chicago-based actor and stand-up comedian. A graduate of The Second City and Columbia College, he’s got the range—onstage, onscreen, and behind the mic. He even hosts a weekly comedy show when he’s not making audiences cry-laugh. Don’t miss him!

03/06/2025

🎭 Chutzpah in the Chi: The Post-Purim Production is bringing the laughs to iO Theatre on March 18! Purim may be over, but the comedy is just getting started.
This lineup is no joke, featuring the hilarious (and 2 Girls 1 Mitzvah Mic Winner) Emma Finn

🚪 Doors: 7PM | 🎤 Show: 7:30PM
🎟️ Get tickets now before prices go up! ($20 advance, $25 day of) 👉 https://ci.ovationtix.com/36725/production/1217637?performanceId=11605302

Emma has only been doing comedy for a year, but a lifetime of mental illness and being the funny friend has prepared her well. Her comedy? Down-to-earth with a healthy dose of sass and sarcasm. Just ask her family: “Wow.” Follow Emma

03/05/2025

💥 Purim is coming next week! Chutzpah in the Chi is here to keep the laughs coming even after the holiday! Join us for Chutzpah in the Chi: The Post-Purim Production on March 18 at iO Theatre! 🎭😂

🚪 Doors: 7PM | 🎤 Show: 7:30PM
🎟️ Get tickets now before prices go up! ($20 advance, $25 day of)
https://ci.ovationtix.com/36725/production/1217637?performanceId=11605302

This lineup is 🔥: Emma Finn, Noah Wolf, and Lexi Costantini
Hosted by: Rebecca Joey Schwab

Limited capacity—our last show SOLD OUT! Don’t miss out. See you on the Chai (18th) of March! 🥳🎭