By Grace O’Reilly
Medill Reports

Gliding down the Italian Renaissance-style hallways of the Drake Hotel and toward the main entrance of the Palm Court Tea Room, Kait Carmody, the hotel’s food and beverage manager, headed toward a hickory podium. She gave instructions to her team on organizing dozens of women’s fancy outfits, for their afternoon tea appointment. 

“She has a bright spot about her,” said Christopher Lindo, a doorman at the Drake. “The unspoken concierge.” 

That was in April. Carmody, 32, who had been a funny, beloved manager by day and a funny, beloved comedian at night, now focuses full-time on comedy.  

She is preparing with her comedy manager, Nicole Skokna, for year two of her “Off the L” comedy tour. The  “Off the L” tour debuted in summer of 2025 with five shows, during which comedians, experienced or novice, had 20 minutes on stage at pop-up locations within a five-minute walk from the nearest stop in the Loop. ​Carmody is looking forward to her series of gigs,  and “Off the L” this summer. She is looking for comedians that fit her plans for the show.  

“I want it to flow so well,” Carmody said. “So if I have a dark comedian who’s going really dark, I want him or her in the middle, and I want two outgoing, bubblier people at the beginning and end of the show, like a sandwich.” 

Until she was 13, Carmody lived in the suburbs of Niles. Her parents decided to move their family, including her, her younger sister and her brother, to Racine, Wis., to help run an Irish pub. Carmody considers herself “Irish Irish, not American Irish” — her father was born in County Clare, Ireland, and her mom’s parents were from County Mayo.   

At 13, Carmody was washing dishes at her parents’ pub. For 10 years, she honed her skills in the restaurant industry, both in the kitchen and restaurant, working as a bartender and server. Then, in July 2021, Carmody landed her first job in the hotel industry as a front desk agent at the Drake Hotel in Chicago. 

When Carmody started at the Drake Hotel, she became fascinated with the hotel’s history, which goes back more than a century. She liked hearing firsthand stories from returning guests and staff about celebrities like Frank Sinatra – and learning from her family that her great-grandfather from Ireland was an elevator operator at a hotel in Chicago. Working in hospitality is “generational,” she said.  

In June 2025, the food and beverage manager position became available. 

“A loud Irish woman managing your bar and you didn’t want us here,” said Carmody, sitting in Al Capone’s rumored 829 suite at the Drake and explaining the bad blood between The Chicago Outfit and the Irish gangs. “That is karma. Should have started loving the Irish back then.” 

In her free time, she performs at comedy clubs throughout Chicago. In January, she did a set at Lincoln Lodge in “The Black Out Diaries,” a 13-year-old weekly continuing series she now co-produces with other dedicated people in the comedy industry, and creator and host Sean Flannery. 10 minutes to tell funny drunk stories or sober ones, through a presentation of photos from the event.  

In early 2025, Carmody began her journey with “Black Out Diaries” when Flannery met her previously at a bar called “Comedy Bar.” 

“When she was booked her first time at “Blackout Diaries,” she thought one of the rules of the show was to go out and make a drinking story that week,” Flannery said. “Which is not our rule at all. She has this hilarious story that she still does on the show, where she becomes a tourist for the day. She rents a hotel room at Navy Pier, and her friends come down and they get face paintings. But she didn’t coordinate. Her friends all wanted to have cute and pretty glamorous face painting. But she had her face painted like a tiger, like a child at a block party. And she has so many photos from it, and the crowd just dies from laughter.”  

​Carmody started her comedy career nine years ago in Grand Rapids, Mich. In her first skit, she focused on growing up Irish Catholic and being raised in her parents’ culture. Carmody likes speaking in front of crowds, dating back to second grade, when she wanted to do the main reading at her first Holy Communion but learned a boy named Andrew got the nod. 

​“And I was like, OK, fine, whatever,” she said, “The teacher, she pulls my mom and me over, she goes, ‘Uh, yeah, Andrew can’t do it. He is actually having a panic attack. Um, can your daughter step up and do it?’ And I was like, ‘I’m ready. Let’s go.’ And so my mom said she knew that I would be some public speaker because she was like, ‘You had no fear.’” 

​For the third year in a row, Carmody hosted “Women’s Christmas” in January at Gaelic Park for the Young Gaelic Association for women members, celebrating the traditional Irish holiday “Nollaig na mBan,” the Gaelic translation of the event’s title. The holiday is a day of rest for Irish women from household chores, with men taking charge of household duties, marking the end of the holiday season. With Carmody as the host, participation has grown from dozens to hundreds. In February, Carmody hosted another comedy show at Gaelic Park. Friends and family attended the event, including her younger sister, Sarah Carmody, who says she is her sister’s No.1 fan.  

“She would always kind of, like, be funny, but also commanding in a way,” Sarah Carmody said.  “It holds true to her, like commanding the stage and hosting events and knowing how to put together a set list and all of the things. So I think it was all meant to be.” 

Kait Carmody, who left The Drake in April, is hosting another show at Gaelic Park June 19.  

“I have decided to put comedy first for the first time,” she said, “And I’m going to be having more gigs.”   

Grace O’Reilly is a magazine specialization graduate student at Medill.