Upcoming Shows
Art Night: An August Affair
August Art Night | August 1, 2025
August lineup is set!! Get Tickets Now>>
We’ve got another eclectic group for you. We’ll hear from a bridge historian (Mitchell Trachtenberg), a sex therapist (Emily Gabelman), an R&B performer (Ngozzi), and 2 stand-up comedians (Rebecca Joey Schwab and William Paik)
We’ve been setting up these events every month for the past 8 years, and we know how to put on a good show. So we hope to see you all there!!
Jokes on Division
See Rebecca’s debut at the Chicago comedy staple - Jokes on Division. This show is free Stand Up Comedy at the legendary Butch McGuire's every Monday night featuring Chicago's best comedians! We've got headliners you would normally have to pay to see at Zanies or Laugh Factory as well as frequent drop ins from nationally touring comics! This is a show not to miss! Arrive early to order food because the kitchen closes at 9 but the jokes and drinks flow all night!
40% off drinks for Industry!
Windy City Late Night Laughs Showcase
Windy City Comedy Fest at iO Theater – Late Night Laughs Showcase
August 7, 2025 | 10:30 PM | iO Theater, Chicago
Close out the night with an electric lineup at iO Theater during Windy City Comedy Fest 2025. Hosted by Chicago’s own Rebecca Joey Schwab, this late-night showcase is packed with some of the funniest rising stars and festival favorites from across the country.
The lineup includes:
Chris Cyr, Aaron Bell, Christine Ferrera, Brooks Sullivan, Jamie Campbell, Mitchell Potts, Hunter Hirsh, Hannah Beck, Matt Brown, and Queeny Bitch.
From smart storytelling to outrageous characters, this show promises a fast-paced variety of comedic styles that will keep you laughing into the night.
Comedy Heavy Weights
Comedy Heavyweights – Windy City Comedy Fest 2025
August 8, 2025 | 9:00 PM | The Lincoln Lodge
No filler—just hitters. Comedy Heavyweights is the Friday night knockout showcase featuring some of the sharpest joke writers and strongest stage presences of the fest. If you're looking for punchlines that land hard and comics who bring the heat, this is your show. This show will be in the Orange Room of the Lincoln Lodge
Hosted by the effortlessly cool Ken Hamlett, the lineup includes:
Mike Shanks, Jamie Campbell, Jon Boyd, Muhammad Saahir, Kristie Hayden, Joe Medoff, Jeff Klein, Kayley Horton, Aaron Putnam, and Rebecca Joey Schwab.
A full night of hard-hitting comedy. No weak sets, no mercy.
The Vagabond | A Variety Hour
Chicago’s Favorite Variety Show
Step into The Vagabond, a one-of-a-kind variety hour bringing together Chicago’s best comedians, musicians, actors, and all-around creative misfits. Rebecca will be performing standup with her keyboard.
Hosted by the charming and quick-witted JD Martinez, this show promises an eclectic mix of performances—from music and stand-up to surprise acts you didn’t know you needed in your life. The Vagabond is all about celebrating bold, brilliant, and delightfully weird talent.
Crunchytown Comedy
Crunchytown Comedy Show at The Playground Theater – Chicago’s Funniest Night Returns!
Crunchytown is back—grab your tickets now through our link in bio! Rebecca is excited to join this lineup! This long-time Chicago favorite is back and bigger than ever, now hosted under a new roof with a full theater space ready for laughs, music, and unforgettable performances.
Clock that Tea Show
A unique comedy experience where comedians spill their hottest tea in front of a live audience!
Get ready for an unforgettable night of laughter, gossip, and absolute chaos at Clock That Tea—the only show where comedians spill their hottest tea live on stage. This is not your average stand-up; it’s part confession, part roast, and all unfiltered truth.
Expect a mix of raw storytelling, hilarious revelations, and interactive moments that will have you gasping, laughing, and maybe even clutching your pearls. Come for the comedy, stay for the tea.
Comedy N’ Cream
Comedy N’ Cream September 4
Comedy N’ Cream: a free comedy show held the 1st Thurs. of each month at Emerald City Uptown Coffee. Catch Comedy N’ Cream, a live comedy show held the first Thursday of each month and showcasing hot lineups of Chicago’s funniest. Located at Emerald City Coffee. Doors open at 7:30pm. Show begins at 8pm. BYOB. $5 donation suggested. Mark your calendars!
Keep Coming Back
Each week we have a different line-up of stand-up, story-telling and sketch the performers share their experience, strength and hilarity on how they recovered or are recovering from all sorts of conditions- getting clean and sober, being ill, weight problems, debt, heartbreak!
Doors open 4:30 and show begins at 5:00 !
Rebecca will talk about losing and gaining weight and being hypnotized from Tobacco and vaping. Talk about healing your inner child…
These are serious life matters but that doesn't mean we can’t laugh at them because laughter is great medicine! if they can get Hey, if these performers can get through it, you can too. You just have to keep coming back!
Chicago Underground Comedy
Rebecca’s Debut on Chicago Underground Comedy
Join Chicago Underground Comedy—ChUC—on Tuesday, September 30 at 8 PM, at Beat Kitchen (doors 7:45 PM). This long-standing indie comedy showcase brings Chicago’s freshest stand-up talents to the stage, combining raw punchlines, personal bits, and unfiltered humor. Tickets are available online or at the door. Bring your best crowd energy!
The Good Guy Show
The Good Guy Show! Hosted by Isabel Amaya and Megan Metzger
A stand-up showcase/unrelenting quest to find Chicago comedy’s Good Guys. Rebecca talks about the good, the bad, and the chosen guys in her life.
Late Night at the Lodge
This line up can CERTAINLY laugh the laugh…
But can they talk the talk? Come watch a brand new line up of comics at Late Night at the Lodge this Thursday to find out!
This show is so much fun! Check out a clip here>>
Talk Harry Potter to Me
Chutzpah Pride: A Queer Jewish Comedy Showcase
Rebecca is producing this one of a kind show!
A Queer Jewish Comedy Showcase
📅 Wednesday, June 18 | Doors at 7:00PM | Show at 7:30PM
📍 Uptown Taproom – 1325 W Wilson Ave
🎟️ $10
Celebrate Pride Month with the most fabulous, fearless, and funny queer Jewish comics in Chicago (and one delightful non-Jewish guest). Chutzpah Pride is back with a fantastic lineup of Chicago’s funniest Queer Jews. Hosted by Madison Burman and featuring Dana Kaye, Gabby Gabe Sklan, Delilah Orizaba, Quinn James and special guest Lio Cunduff.
🎤 Hosted by Madison Burman (She/Her) Madison Burman is a born and bred Chicago-based comedian. She has performed at Second City, the iO, Blanket Fort, and the Lincoln Lodge. A chronic over-sharer, she loves talking about her eccentric family, toils of the dating scene, and discussing how all Muppets are canonically Jewish. Follow her @SuchisMadison
🌟 Dana Kaye (She/Her) Dana Kaye is a comic, mother, and lifelong Chicagoan. She performs at venues all over the city, including Laugh Factory, Second City, Zanies, and The Lincoln Lodge. Follow Dana on Instagram and TikTok @DanaKaye23
🌟 Delilah Orizaba (She/Her) Delilah Orizaba is a full-time therapist and part-time standup. You’ve seen her perform at The Future of Comedy Festival, The Latina Comedy Festival, and Zanies. She’s a Scorpio sun; Capricorn Moon and Rising. Follow Delilah @isntthatdelilah
🌟 Gabby Gabe Sklan (He/She/They) Gabby Gabe Sklan is a comedian, clown, producer, and host of the Bad Boyhavior podcast whose comedy career started in Wild Western Massachusetts before they came careening into Chicago’s comedy scene and become a regular on local showcases at Lincoln Lodge, IO, and The Annoyance. Known for slow-burning stories and earnest gags, Gabe always delivers a charismatic and hilarious performance. You can expect every subject to be discussed with all the respect it deserves, which in some cases is none at all. Follow Gabe at @gabegabegabegabegabegabe
🌟 Quinn James (Oy/Vey/They) Quinn brings a nostalgic yet edgy vibe to the stage, blending Y2K humor with Gen Z irony. Whether it’s their physical comedy, unique storytelling, or captivating stage presence, Quinn leaves every audience wanting more. They’ve been lighting up stages across Chicago and beyond, including the Loons on the Lake Festival!. Follow Quinn at @quinnjamescomedy
💫 Special Guest: Lio Cunduff
The non-Jewish queer palate cleanser we didn’t know we needed. Come see why they fit right in.
Don’t miss Chicago’s only Queer Jewish comedy show, full of chutzpah.
Judging the Throw Down Gauntlet
Join the audience and see Rebecca Judge!
Be part of the audience and choose the final monthly winner! Check out Rebecca Joey Schwab judging this special event. They win bragging rights! They win a SUPER COOL TROPHY! They win some cold hard CASH and they're very own appearance on a future showcase!
Jewish Dating Live
Get ready for an evening of laughter and matchmaking as ChiTribe and Chutzpah in the Chi present Chicago Jewish Dating Live on June 11 at 7pm at Barcocina in Lakeview! Hosted by the funniest Jewish duo, Rebecca Joey Schwab & Seth Davis, this one-of-a-kind event combines stand-up comedy with a live dating game show featuring Chicago's most eligible Jewish singles.
This game show combines rounds like “Phone-Your-Parent”. Think wheel of fortune meets Jewperdy, featuring singles in their 20s and 30s.
Whether you're single, taken, or just a fan of good comedy, this event promises plenty of laughs and maybe even some unexpected matches.
Want to nominate your single friends? Or apply to be a contestant?
After the show, mingle with contestants and maybe introduce them to their perfect match—you might just be the ultimate Jewish matchmaker!
Jewish Dating Live Details
📅 Date: June 11, 2025
⏰ Time: Doors open at 6:30 PM | 7–9 PM
🧑🤝🧑 Ages: Singles and Couples
📍 Location: Barcocina Lakeview | 2901 N Sheffield Ave, Chicago, IL
Bachelorette Private Event
Private Bachelorette Party Comedy Show
Rebecca is hosting a private Bachelorette Party comedy show made specifically for the wonderful Persian Bride. This is a private event that features a special show and interactive games with the participants. Email Rebecca@ChutzpahintheChi.com to book Rebecca for your Bachelorette party!
Hammered Herstory: Chicago's Funniest Drunk Comedy Storytelling
From the team that brought you Date my Friend, Hammered Herstory combines women’s herstory, comedy, storytelling and everyone’s favorite thing: booze!
The concept is simple: in each episode, six presenters research a noteworthy, famous or infamous woman (or event) from Herstory! Then they get buzzed and go on stage to tell YOU all about it!
The theme of the June 1 show is Women of Herstory for PRIDE! Rebecca will be presenting on Gertrude Stein.
Bad Jewish Momz
Oy! Get ready for a night of laughs on Saturday, April 19 with the Bad ‘Jewish’ Momz of Comedy as they take over Congregation BJBE in Deerfield! These hilarious Jewish ladies are bringing their unfiltered humor and kvetching expertise to the stage; you won't want to miss it.
These ladies are leaving the guilt trips at home and serving hilarious jokes about everything from raising ungrateful children to navigating life after brisket. You'll laugh so hard, your bubbe will hear you from Florida!
Please share this hilarious event with your synagogue members – perhaps on your e-newsletters and on social media. And feel free to organize a temple group for a fun night at BJBE in Deerfield.
Comic Court
All rise for Comic Court! Chicago's #1 Comedy Court Show (it's the only one) returns to The Lincoln Lodge every 2nd and 4th Tuesday at 9PM! Comedians pose as lawyers to debate ridiculous cases and YOU are the jury.
Comedians take turns coming on stage and laying out their arguments. Then they both take questions from the audience (don't worry if you're shy, you can choose not to raise your hand!)
This hilarious, one-of-a-kind show involves a lot of crowd interaction, making it perfect for dates, afterwork drinks and large groups. Comic Court is now in session!
Laughs and Drafts
Get ready, Skokie! Laughs and Drafts is back, and this time, we’re bringing the comedy to Sketchbook Brewing Co. Join us for a night of hilarious stand-up, great beer, and an electric atmosphere. Featuring your favorite Laughs and Drafts vets plus some brand-new talent, this lineup is stacked with comedians guaranteed to keep you laughing all night.
Come for the laughs, stay for the pints! Enjoy exclusive drink specials during the show. Mark your calendars and grab your crew—we'll see you there! 🍻🤣
📍 Location: Sketchbook Brewing Co. – Skokie Taproom (4901 Main St, Skokie, IL 60077)
📅 Date: Thursday, March 20th
⏰ Time: 8:00 PM
🎟 FREE SHOW!
Chutzpah in the Chi: The Post Purim Production
Purim might be over but that does not mean we have to stop laughing this March. Join Chutzpah in Chi on March 18 at the iO Theatre for more unfiltered chutzpah featuring some of the city's funniest Jewish comics. Doors open at 7, the show is at 7:30pm. Grab your tickets now before prices go up ($20 in advance, $25 day of). Buy tickets here>>
This month the show is at the iO Theatre and capacity is limited (our Christmas Eve show sold out!) Secure your spot now and see you on the Chai (18th) of March.
Hosted by Rebecca Joey Schwab, every month Chutzpah in the Chi travels throughout the Chicagoland area bringing Jewish joy and Jewish humor to the stage.
The Post-Purim Production Lineup: Emma Finn (2 Girls 1 Mitzvah Mic winner), Noah Wolf, and Lexi Costantini.
Private Chabad Show
Rebecca performs throughout the Jewish community with Kosher material to fit every crowd. She is excited to perform for a special private Purim celebration on March 14 for the Chabad of Norwood Park. Catch Rebecca’s Kosher comedy throughout the city, sponsored by any religious organization.
Laughter Hours
Laughter Hours Comedy Showcase features the best comics in Chicago every Friday. On MArch 7, Rebecca Joey Schwab is making her Laughter hours debut with her first guest spot. Laughter Hours is Comedy + jazz kind of show every Friday at 11pm at the Lincoln Lodge.