The Doughboys are at The Den Theatre this week
CHICAGO COMEDIANS IN THE NEWS
Joel Kim Booster and his husband, John Michael Sudsina were featured in the New York Times Vows section yesterday, where they shared how they met and fell in love—along with some romantic behind-the-scenes details from Joel’s many hit comedy projects.
Jimmy Carrane and Kim Greene Hiller appeared on WGN’s Daytime Chicago to talk about the Laughing Academy’s upcoming 15th anniversary celebration (see more below).
Lots of extremely fun and memorable moments in yesterday’s Bears’ playoff game including Mike Bridenstine‘s Verizon spot. Mike is also the author of the critically acclaimed The Perfect Amount of Wrong chronicling the rise of Chicago’s alt-comedy scene. It’s one of my all-time favorite reads. Now adding to my list of best books about comedy, his new Kansas City Comedy: The Unbelievable True Story of Stanford & Sons, Its Outlaw Owners and the Most Infamous Stand-Up Sets of All Time.
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Following are twelve comedy highlights this week, just a fraction of all the city’s possibilities. For a (much) bigger list, please see my 2026 Advance Ticket Alerts. Please always confirm all details before leaving home … especially when it’s fifteen minutes to frostbite.
MONDAY, JANUARY 19
The Armando Diaz Experience at iO, 7:00 p.m. Created in 1995 by Adam McKay and David Koechner, the Armando is one of Chicago’s big contributions to worldwide improv. Early casts were led by Del Close and included Jimmy Carrane, Rachel Dratch, Tina Fey and Amy Poehler.
TUESDAY, JANUARY 20
Chicago Underground Comedy at Beat Kitchen, 8:00 p.m. Showcasing Chicago’s great up-and-coming stand ups.
WEDNESDAY, JANUARY 21
Low Key Lit at Second City, 7:00 p.m. A new show at Second City promising the biggest local and national names in stand up and improv.
The Doughboys at The Den Theatre, 7:15 p.m. Nick Wiger and Mike Mitchell’s popular food podcast has been featured on Good Morning America and The Simpsons. Through January 24. It looks like tickets are sold out, but … always worth calling the venue and/or showing up to see if there’s space at the last minute. Also, check my 2026 Advance Ticket Alert Calendar often to avoid missing out.
THURSDAY, JANUARY 22
Chicago’s Best Standup at Laugh Factory, 7:00 p.m. & 9:00 p.m. Early show: Luke Null , Subhah Agarwal, Vik Pandya, Noe Noel, Maeve Devitt. Late show: Luke Null, DJ Rybski, Peyton Ruddy, Deanna Ortiz, Maeve Devitt.
FRIDAY, JANUARY 23:
Maggie Winters at Color Club Ballroom, 9:30 p.m. This award-winning comedian can also be seen on the third season of The Righteous Gemstones (HBO). TNK Festival.
Melani Sanders at Wentz Concert Hall & Fine Arts Center, Naperville, 6:30 p.m. The founder of the We Do Not Care Club is speaking about launching an international movement and her new book The Official We Do Not Care Handbook, all of which have made women everywhere feel comfortable speaking up and happier about life and choosing what to care about. Her tour is selling out nationwide but amazingly, there are still tickets left for Friday. If you aren’t familiar, see her recent appearances on CBS Mornings, The Drew Barrymore Show, Sherri and Instagram.
SATURDAY, JANUARY 24
Bad Momz of Comedy at Sandwich Opera House, Sandwich, 7:30 p.m. With Orly KG and an always acclaimed lineup. As seen on The Kelly Clarkson Show.
Jimmy Carrane & Laura Hugg at Laughing Academy, Glenview, 6:00 p.m. The We Are Not a Glum Lot Recovery Show.
15th Anniversary Stand Up Special at Laughing Academy, Glenview, 8:00 p.m. Jimmy Carrane, Tyler Fowler, Vik Pandya, Kim Greene Hiller
SUNDAY, JANUARY 25
Brad Upton Live Special Taping at The Den Theatre, 5:00 p.m. & 7:15 p.m. The Better With Age Tour.
Comedian Stick Live Special Taping at Riddles, Alsip, 7:00 p.m. Reflections on childhood to adult life.