Places/place
Chicago
2016-12-13, 1 mention2017-07-29, 2 mentions2017-12-11, 1 mention2018-01-08, 1 mention2018-05-02, 1 mention2018-06-13, 1 mention2018-06-20, 1 mention2018-08-16, 2 mentions2018-09-20, 1 mention2018-10-05, 1 mention2019-04-21, 1 mention2019-12-29, 1 mention2020-02-09, 3 mentions2020-06-14, 1 mention2021-07-18, 1 mention2021-08-15, 1 mention2021-08-29, 2 mentions2022-01-18, 1 mention2022-02-14, 1 mention2022-05-08, 1 mention2022-05-29, 1 mention2022-10-02, 1 mention2023-03-03, 3 mentions2023-04-30, 1 mention2023-10-07, 1 mention2023-10-22, 1 mention2023-12-23, 1 mention2024-01-20, 1 mention2025-06-28, 1 mention2025-10-04, 1 mention2025-11-15, 1 mention2025-11-29, 1 mention
Tim’s take
Most of the time Chicago is his stock example of urban collapse — corruption, shootings, murder rates, kids storming cars — a line he reaches for the way other comics reach for Detroit 28:20 1:22:37 33:25 30:49 14:57 59:56 25:21. It is a punchline more than an argument, and he admits as much when he jokes that gang violence there is basically advertised the same way a resort hides its jellyfish deaths 30:49.
Lori Lightfoot gets her own recurring bit inside that shorthand: he says he loves her precisely because she's a petty, chaotic villain, and admits that if he actually lived under her he'd find the crime less funny 14:05 39:20 45:20.
Every Reference (39)
"where to go. He has never been on a plane. Where should I go, Chicago? He is 63 years old and he has never been on a plane. I'm thinking"
Holiday Plans, Smith & Wollensky's, and Ray's First Plane Trip — We Are The News+29s into the segment"It's like this is people are not. Yeah. This is not cuisine to be like argued about. This is like they pretend like they were like, oh yeah, we're the second city. You like maybe the eighth city, not the second city."
"I should do the rehab gig on Friday and then I and I and I fucking do two shows It's a nice in the middle and I mean Chicago man, Chicago. They are they're drinking"
Farting Through Dinner with Hannah Before the Zanies Weekend Shows — Finding the Kumps+185s into the segment"like the only city to create a food. Yeah. Like a type of food. Chicago's good. Chicago's got a lot of Chicago's five. I don't think they"
Uncle Tommy the IRA Lunatic Choking a Guy Over Ireland — Stewed Reunion (with Mike Recine)+130s into the segment"the chicken-booked red-eye was just like, we could take it to Chicago. It was something ludicrous, but she's like, we could drop you"
"It's just so funny. I mean they used to we drove we drove to Chicago, Miss Carla's a bell We drove to Chicago once her mom like on"
"through the 11th. Come on out. You're gonna love it. It's Chicago Chicago comedy of Broadway Lexi to Kentucky August 16 through the 18th"
"August if you want to see me I'm gonna be in Lexington, Kentucky, Chicago, Illinois Providence, Rhode Island the show in the Hamptons just"
"best it was no I've never had a better burger. So if you're in Chicago, what else you all? Like a Dijonay sauce, American cheese, bacon,"
Go Alone: The Philosophy of Solo Dining and Teenage Weed Circles — The Middle Of The End+23s into the segment"miker who opened for me in North Carolina He was in she lives in Chicago and I took him because that you can't eat alone. That's not to"
"years, the crime has gone down. They went after the gangs and in Chicago, that's the same thing. The gangs are committing the murders,"
"coast because what are you gonna do? What are you gonna go to Chicago? Okay, I've heard about the truck watching a video about the Detroit"
"they just, you know, people from the south side and west side of Chicago, cops not reading the memoranda rights just throwing them in this"
"LA to an extent even though it's the suburbs or if you live in Chicago yes you're still a boomer but to me the real boomer experience"
Boomers, Suburbs, and the Auto Lobby's American Dream — #180 - History Hyenas | The Tim Dillon Show+87s into the segment"in 2009 and uh you know he was you know from you know I mean Chicago is just the most corrupt state in the Union he was removed from"
Blagojevich Enters the Picture: Chaos, Cons, and a Fake Wood Floor Tangent — #186 - Blagojevich | The Tim Dillon Show+279s into the segment"was an amazing uh fun lady I remember the first time I was in Chicago because that's where she came from came from the suburbs her mother"
Road Trip to Chicago and Meeting Blagojevich's Wild Mother — #186 - Blagojevich | The Tim Dillon Show+7s into the segment"what I'll think I'll always think about her when I think about Chicago I'll always think about that period of my life you know sort of"
America's Love Affair with Criminals, From the Mafia to Trump — #186 - Blagojevich | The Tim Dillon Show+129s into the segment"opioid addiction how many these people care about the southside of Chicago and the shootings that are happening there or do these people"
Is Capitalism Reformable, or Just Socialism-Signaling? — #204 - Katie Herzog | The Tim Dillon Show+385s into the segment"remember being in chicago the first time and that's not even chicago they don't people from the midwest don't even consider that right"
Midwest Considerate vs. New York Tough, and Bashing Turkey Sandwiches in New Orleans — #261 - Please, Die Alone | The Tim Dillon Show"to if you drive around this country enough the new yorks and chicagos and miami and la these are the anomaly the vents can we just"
Flint, Ghost Towns, and Relocating Dying American Cities — #264 - Time Is A Fat Circle | The Tim Dillon Show+120s into the segment"Now, yes, if I was someone who lived in one of these places in Chicago that was, you know, suffering from inordinately, and I mean to"
VIP Limousine's Brutal Rebuttal to Lightfoot — #266 - Lightfoot Strikes Twice | The Tim Dillon Show+150s into the segment"somebody. This is this is who she is and this is how she runs Chicago. a petty, vindictive chief executive who will not take any blame."
Lightfoot as a Trump-like Sociopath and Climate Doom — #266 - Lightfoot Strikes Twice | The Tim Dillon Show+32s into the segment"uh one of the greatest mayors of one of our greatest City in Chicago um with a murder rate I believe is like uh half it's like one"
Lori Lightfoot Shakes Down a Chicago Car Dealer — #284 - Prozac Play-Doh | The Tim Dillon Show+17s into the segment"there's no one that supports her in the state for all of our Chicago fans the one the only the great Lori Lightfoot that we believe"
Lori Lightfoot Blames Remote Learning for Carjackings — #287 - Drug Recognition Expert | The Tim Dillon Show+39s into the segment"get it I understand it's like certain you know if you go into Chicago and you go hey is it safe they go yeah it's great come on in sure"
Booking the $15,000 Silky Oaks Lodge Disaster — #297 - The Lodge From Hell | The Tim Dillon Show+238s into the segment"all these loopholes and then and then you know go sell them in chicago you can't go from another state and get an easy one and then travel"
NRA Convention in Houston and Kevlar Fashion for Kids — #300 - A Unique Experience with Yannis Pappas | The Tim Dillon Show+30s into the segment"try and uh you know Lori is uh or the gift listen if I lived in Chicago I'd probably be angry but I don't so it's pure comedy I wanted"
Tour Dates, Louis CK's Website, and Bobby Kelly's Special — Louis CK | The Tim Dillon Show #317+101s into the segment"this woman um it is a sad day in America but a very sad day in Chicago um because we have lost one of the best um an advocate for chaos"
"last year in Chicago just out of curiosity if we can get that Up Chicago a violent crime there has been a major problem there are like"
Lori Lightfoot Video Montage: Crime, Vaccine Threats, and Press Meltdowns — The Tim Dillon Show #336+56s into the segment"called her out on anything anyone that would mention a fact about Chicago the shootings the murders the crime she hated it she was like"
"back we're back we're still on the road we've got a few days Chicago Theaters almost sold out in Chicago the Masonic in San Francisco"
Cold Open: Dubai Tax Purposes and Tour Plug — The New Braveheart | The Tim Dillon Show #344+34s into the segment"I mean Chicago theater is my favorite theater in the country Chicago is my favorite Market to do ComEd great comedy Town Chicago Boston"
Tour Dates and Sign Off — A Time Gone By with H. Foley & Kevin Ryan | The Tim Dillon Show #364+59s into the segment"hey about Chicago you go over there how about you kill people over there instead of killing them in your back in guns are illegal there and look what's going on"
The Long Island Mall Military Recruiter — Knuckleheads & Dodo Birds | The Tim Dillon Show #366+2s into the segment"Boston Massachusetts let Connecticut which is the Foxwoods Casino Chicago Illinois Dana Beach Florida Phoenix Arizona Atlantic City New"
Santa Claus Cold Open and Tour Dates — A Christmas K-Hole | The Tim Dillon Show #374+31s into the segment"the Wilbur almost sold out probably adding a fourth Foxwoods Chicago we're going back to the Improv you know why because it's a lot"
"won't go that way where it's like flash mobs of children. I mean, Chicago's just fully got flash mobs of teenagers storming"
Getting Pulled Over on Long Island and Distrust of Cops — Zohran Mamdani, Political Rage, & The Hunt | The Tim Dillon Show #450+83s into the segment"troops because we're going into Portland and we're going into Chicago." This is a bit psychotic. Let's listen to this very important"
Pete Hegseth's Fat Generals Speech and Troops in American Cities — They Got Greta, A.I. Hollywood, & The Battle For Tik Tok | The Tim Dillon Show #464+73s into the segment"Fort Lauderdale this weekend. It's sold out all except for one. Chicago's sold out. We've added a show. We will see you in um Fort Lauderdale,"
Tour Dates and Sign-Off — Lame Duck Donald & The Immigration Nation | The Tim Dillon Show #470+11s into the segment"each other. Stop doing that. I'm thankful I didn't get shot in Chicago. They shot seven people a few blocks away from my hotel. I'm thankful"
Thankfulness Closer: Middle East Peace, Chicago Shootings, and End of Humanity — Wicked?, A Terrible Life, & The Golden Age Of Travel | The Tim Dillon Show #472+85s into the segment