A Daily Guide to Chicago Comedy Shows in May 2018

May 1: Fried Hard Comedy Tuesdays at Rockin Horse Saloon & Grill

Hosted by Chicago comedian Big Keef, this weekly comedy showcase (recently relocated to Rockin Horse Saloon & Grill in Oak Forest) has been running for more than five years.


May 2: Boy/Girl Sleepover at The Pony Inn

This bi-monthly showcase consistently lands top-notch headliners, has an amazing following and always delivers. This show features an impressive line-up and closes out with Chicago great Chelsea Hood.



May 3: April Macie at Zanies

This killer comic was on "Last Comic Standing," is a frequent guest on Howard Stern and is in town for seven shows over four nights at Zanies.



May 4: Chistosos en Chicago at Laugh Factory

A Cinco de Mayo show one day early and all in Spanish. Featuring Jaime de Leon and Sonal Aggarwal.








May 5: H. Jon Benjamin at Wilson Abbey

Actor and comedian H. Jon Benjamin makes a stop at Wilson Abbey on his book tour.








May 6: Ladies' Night Out Comedy Jam at Riddles

Rush Entertainment and Rodney Lumpkins present this night of comedy featuring B-Cole, Erica Clark, Mickey Housley and Erica Clark.


May 7: Camp: A Comedy Show at Village Tap

This weekly comedy showcase with a summer camp scene goes year-round in a beer garden and always delivers a stellar line-up.



May 8: Michael Palascak at Zanies

Another great comedian who got his start in Chicago and now calls LA home. Tonight marks the first of nine shows over six nights at Zanies for this "Last Comic Standing" finalist.



May 9: Bad Taste - Cumback Show at The Charnel House

Handbag Productions and Mo Less promise "a revue of queer camp curiosities, bringing you Chicago’s most hilarious and shocking performers guaranteed to make you scream, cry, and howl." And this is the cumback show.






May 10: Jeremy Piven and Friends at Laugh Factory

The Evanston native and "Entourage" star is hitting the Laugh Factory stage for five shows over three nights. He told WGN Radio "All roads have led to this."






May 11: Funny Ha-Ha at The Hideout

This monthly show always has a killer lineup but this particular (mother-centered) night promises two especially special appearances: "SNL" alum Julia Sweeney and Chicago author Megan Stielstra.







May 12: Strip Joker: Mom Bod at Uptown Underground

"Dad Bod" is in the popular lexicon far more than it deserves, especially when that Mom Bod is much more deserving of the limelight. This popular "body positive stand-up show" takes the time pre-Mother's Day to celebrate the mom bod with an incredible line-up of performers.

May 13: Festival of Laughs at Arie Crown Theater  

A comedy show at Arie Crown Theater with a crazy-good line-up including Sommore, Don “DC” Curry, Tony Rock, Arnez J and the great George Wallace.

May 14: Chicago's Best Stand Up at Laugh Factory

This is a weekly show but this specific show may actually feature the literal best stand-ups in Chicago on one stage right in a row: Tim McLaughlin, Kristen Toomey, Russ Williamson, Em Brown, Matty Ryan, and Kyle Scanlan.

May 15: Little Sarah's Big Night Out at The Empty Bottle

As the promotional poster suggests this will be a family comedy show. As I mentioned in my Chicago Tribune review of her last solo show at The Empty Bottle, Sarah Sherman's comedy is comparable to Jim Gaffigan, Gabriel Iglesias or Jeff Foxworthy. Just good old fashioned comedy without all the gross stuff these new comedians INSIST on putting in their acts.

May 16: Megan Gailey at Zanies

Returning Chicagoan alert! Gailey is in town for three nights at Zanies. Always check out this top-notch comic when she's in town. One, because she's funny, Two, because then when she blows up you'll be able to say you were ahead of the curve.

May 17: Heather McDonald at City Winery

This multi-hyphenate is a stand-up, podcaster, author, screenwriter and weekly columnist for "InTouch." Her stand-up special "I Don't Mean to Brag" is hilarious and she's in town to both do stand-up and to record an episode of her "Juicy Scoop" podcast. The City Winery shows keep selling out so there are now three spread out over today and tomorrow. 



May 18: Aries Spears at Chicago Improv

Another returning Chicagoan headlining a local club. Aries Spears is in town for six shows over four nights - make the drive to Schaumburg to catch one of them.


May 19: Dulce Sloan at Zanies

Three shows - but one night only - at Zanies. Catch this hilarious "The Daily Show" correspondent before she goes on to offend everyone at a future White House Correspondents Dinner.


May 20-23: LaffMob's Laff Tracks recording for truTV at The Promontory

A new show for truTV - where the creator makes videos for stand-up sets and intersperses the videos with the set - is recording a bunch of live stand-up shows at The Promontory in Hyde Park this month. To clarify: FREE comedy shows at an incredible venue. Check the lineup to see when you want to go - there are early and late shows each day and almost every show features at least one Chicago comic. And here's the full list of Chicagoans so you know who to look for: "A Dope Ass Comedy Show's" Dave Helem, "Helltrap Nightmare's" Sarah Sherman, "Faded's" T. Murph, MiHiChi's Calvin Evans, Corey Bell, Kevin Simpson, Vanessa Fraction, and Matteo Lane.

May 24: Piff the Magic Dragon at Comedy Improv

Is dressing up in a dragon costume and doing magic tricks a gimmick? Yeah duh. Also, sometimes gimmicks are hilarious. This little dragon with a bad attitude (and his dog Mr. Piffles) are genuinely funny.





May 25: Durkins House Party Comedy Show at Durkins Tavern

Every Friday for $20, Durkin's Tavern offers all you can eat pizza and all you can drink. There's now a comedy show/open mic happening at the same time. Is the pizza great? Are the drinks top shelf? Is the comedy super hilarious? For $20 really just enjoy all of it that you can.

May 26: Angelo Lozado at The Comedy Bar

This longtime comedian serves as the opening comic for "The Daily Show with Trevor Noah" and opened for him at The Chicago Theatre when I reviewed two years ago for The Chicago Tribune. From that review: "Opener Angelo Lozada... gave a winning 30 minutes of affably scatter-shot comedy, complete with a surprising (and surprisingly effective) amount of crowd work. Lozada seemed so comfortable working such a large room it was almost as if the audience had accidentally come to see him, and would have (almost) been fine with that."

May 27: Funny Miss Brown & Fam: Chicago Edition at Output Sports Lounge

I'll be honest: I have not heard of Eljae Brown. But if she can put together a line-up like this - including both Brian "Da Wildcat" Smith and comedian/producer Eli Hamiltorn - for a Memorial Day Weekend show in Chicago (in the afternoon instead of at night) then I'm willing to bet she knows what she's doing.



May 28: Sex Positive at iO

This monthly show - hosted by Ashley Victoria - is a mix of stand-up, burlesque and music that talks openly - and frequently hilariously - about (what else?) sex.






May 29: Marcella Arguello at Zanies

A regular opener for Felipe Esparza, Marcella Arguello is at Zanies for two nights in a row starting tonight. Whip-smart with a unique stage presence and a biting wit, she also writes for "Bill Nye Saves the World."

May 30: The Onion Comedy Arts Festival at [EVERYWHERE]

This is the Lollapalooza of comedy festivals, with big names appearing all over the city for five days straight (from tonight through June 3rd), from Jo Firestone to David Cross to Bob Odenkirk (and friends) to Chris Gethard to Chicago's very own Helltrap Nightmare.

May 31: Deon Cole at Chicago Improv

Originally from Chicago, Deon Cole is not just a great example of the incredible stand-up talent Chicago produces but also a bonafide tv star. He's at the Chicago Improv for four nights of shows.