Your Guide to October 2026 in Chicago

0:00We like to say Illinois is in the middle of everything. You can visit Chicago to soak up them lakefront views, check out our neighborhoods, or indulge in iconic cuisine while discovering world-class museums. You can take the scenic route and chase change in colors across state parks, forests, and trails. You can check out small-town Illinois for quaint shops, cozy eateries and seasonal celebrations, or be nostalgic out on Route 66 with neon-lit diners, vintage motels, and historic landmarks. Find exactly what you're looking for and even more at enjoyillinois.com. This is CityCash Chicago. I'm Jacobi Cochran and here's what Chicago is talking about. Adora, if you could hear any Chicago voice making announcements on the CTA, who would you pick? Hands down, Jacobi Cochran.

1:00Oh my god, you did not have to do that. It's true. We pay you, but we don't pay you for that. You would add a little sauce to it. Even when we got on this reporting, you sang my name a little and I was like, oh my god. Imagine feeling that way on the CTA. You hands down. The door will open on the left. Who doesn't love that? That's all. So nice. How do we start a petition to get you on this? That's my next question. Adora, now me, Goday with some of the best compliments in the game. Welcome back to the podcast, my friend. You're welcome and you deserve it. So thanks for having me. Lee over to you. If you can hear any Chicago voice, say as me, who would you have making your announcements announcing your your train stops? Man, well, if it's not Jacobi Cochran, who big of a... Yeah, who we all want to hear. So CTA, listen to our plea. I got to say, I love the like hard Chicago accent of Van Meenopoulos WB Easy News.

2:02I love Dan so much. I would love to hear him be like, doors opening on the right. Don't be a jack off and stand in the middle. I would venture him in my head. I don't even know how to hold you. Wait, I got home first name based with Dan. I felt like I accomplished something. I would not even go back to you. No way. It's like I accomplished something in the city of Chicago. That's pretty big. That is another amazing contributor in the building with us. Lee, John Greco, Lee. Welcome back to the podcast. Always good to be here, Jacobi. Luckily, at least for a little while, there will be another Chicago and coming through those CTA speakers as Grammy Award winner, Laila Hathaway, the eldest daughter of the Chicago legend Donnie Hathaway, will be partnering with CTA according to the tribe. There's going to be making announcements on platforms across the city. This is in celebration of her new album May and Chicago, which dropped today. I was listening to a couple of songs 47th Street yesterday. That's a go and J.I.V. is on it.

3:04It also is today is the birthday of her late iconic father. I think you can see a Donnie Hathaway mural on the small chival over there in a higher part. One of my favorites in the city. If you want to read the entire release, please head over to the tribe's website. In that spirit today, we've got our guide to October, 2026 in the land, including a little budget and election preview tips for the Chicago Marathon. And I'm going to need some spots so I can go get all of my costume needs figured out. And so please make sure y'all hit us up 7737 A zero zero two four six. But let's start here. What is something you are looking forward to in October? So as we look out the window right now, it's a little rainy. I know, but let's keep it a little optimistic. Adore, what is something you are looking forward to this month? Oh my gosh. So event wise, I'm looking forward to two things. A, the Chicago Marathon, God, I love it. Okay. One of the six major marathons in the world obsessed. And I'm also looking forward to Chicago Fashion Week, which the details are not all fully out yet, but it's going to be October 9th to 19th.

4:08And they always do cool events where like they pull in museums, for example, or they have like clothing swaps. So in addition to like the traditional runway show. So I'm excited for both of those things. Okay, Chicago Fashion Week October 8th through the 18th. But I got asked, are you a marathon runner yourself? I am a marathon runner myself. I say I'm retired because I don't think I'm forcing myself to do it one anytime. So right now, I'm kind of over it. How many of you does? You know, I've done four. Oh my lord. That's a lot. That's a lot on the show. That's a lot. Thank you. It's a lot of my toenails too much information probably, but my husband is like, wow, I'm so glad you don't run marathon anymore because you're toenails. Now I'm coming for the feeds, man. I'm going for the feeds. I know. I know. Why I'm hitting down this podcast, but are you though? You're just like it's already out there. You're just warning people, Adore. Lee, what is something you are looking forward to this month? Not to be a basic fall girl, but I love apple picking, which obviously you can't do inside.

5:10It was Chicago, but one to Cooper's last year, it's spelled KU. I P E R. A posture for yes. Great, great apple orchard. They have somebody before you go out in the orchard, like, give you a guide to how to go out there. They have a guide on like all of the apples that are in season because it's not like all the apples come out at one time. It's like, oh, the Macintosh are in late September and the Jonah Gold are in, you know, mid October or whatever. So I'm looking forward to going there, getting some crisp apples. I'm not going to mess with any kind of like red delicious. I don't even know if they have red delicious out there, but I was talking with my friend Brittany and we're like, those who are those four? They're disgusting. Let's see. Let's see. Apple varieties that they get. Oh, yeah. Let's go down the list. They have a lot. They have a lot. They have a lot.

6:10Yes. They have like granny myth. They have late October. That's late October. Yep. Got some of those last year. Oh, that's interesting that they have different breeds throughout the different months. That makes sense. Yeah. Exactly. Hold me this because I like apple picking is the kind of thing that I don't organically think about. But then when someone mentions it, I'm like, oh, yeah, obviously I would love that. It's so nice. It's really. I like a good honey Chris. I like a good honey. Honey Chris. Good. Everything. Also here. Cooper's got something. It has a great bakery. Yes. We also, that's another thing we got some of the apple cider doughnuts. They have many varieties of doughnuts as well. So that's kind of key. It's nice to go with like a group of friends and maybe get like a little, a little half dozen pack or depending on how many of you are and then you can try different ones. Such a vibe. When we went last year, it was the perfect October day where the sky was just bright blue, no clouds, but it was crisp out and cold.

7:11And that's what you want. You don't want it too hot. You don't want it too cold. Just right. And yeah, so I'm really looking forward to that. I'm so glad you told me about that. Thank you. One thing. I guess both looking forward to, but also not looking forward to. That's like the end of farmer's market season. So like a lot of. Some of my favorite farmer's market in the season are closing up shop in October. So the 95th Street Farmers Market last day is October 25th. My boy is over there. 61st Street Farmers Market. I spent a couple of weekends there. Their last day is Halloween, Austin, Town Hall Farmers Market ends October 29th. El Paso is over this weekend. Oh my gosh. And so yeah, quite a few farmers market Jefferson Park. October 25th. Lee, you were bragging because your farmer's market isn't over until November. Yeah, I was going to say, even though there are lots of farmers markets closing this month, there are quite a few that go through almost the end of November, including my favorite,

8:15the Lincoln Park Farmers Market, which is not to be confused with the Green City Farmers Market in Lincoln Park, but Lincoln Park Farmers Market is in front of the high school. So yeah, we still have so much in October, November in terms of squash. I love squash season. Favorite, favorite time we have apples. We have apple cider. We have meat. So yeah, we have everything that you need for your Thanksgiving table. So come and get it. We are open till the second to last weekend in November. So like not Thanksgiving weekend, but the one before I imagine there will be a rush because worker park farmers market closes October 25th. The one I met every weekend closes on Halloween, the South Loop Farmers Market, Roscoe village, Ravenswood, all the last weekend of October, also the Pullman Farmers Market. And so while there are a couple still open, if you haven't gotten out there, please make

9:17some time. I know the weather hasn't been great every single weekend. I know the South Loop Farmers Market, 61st Street have been canceled a couple of weekends, but if you can find some time this October, look up the one closest to you or one of your favorites, get out there, spend with your local vendors. And then my last thing I'm looking forward to because since this is coming out on Thursday, means the socks are either playing a game today to go to the next round, or we already rest and then relax. Because we won our first game in five years. Amazing. Six to three already on. Oh my God. Socks. 12. I'm just I wanted to bring up, by the way, did you guys see this like Twitter post that is going viral about the guy who's like, I've never seen a native Illinois person wearing a socks hat. You must be smoking some right because what are you talking about? I think the socks cap go bar for bar with the Yankee cap in these streets. If you really tap the in, people is wearing the socks cap all over the world.

10:20Yeah. It is if not the one of the most five logos in all of professional sports. So the idea that only it's like we all we can all admit. We know how people treat the socks in the city and around the city. We know that she does like a stepchild. We get it. We ain't pretending like we the number one franchise in the city, but to act like everyone don't agree that we got the best food and the best merch throughout your mind, bro. The merch is so good. The merch is so amazing. The merch is so amazing. So we are here. I'm hopeful that we get a couple more games, you know, from my friends on the other side. Hmm. I hope you're still playing the day. Providence town 1947, one room to massive ass egos in the moment American theater called Fire Johnny, a leaky is Tennessee Williams, brilliant, desperate and searching for his Stanley, Kawaski, Jacob, Moskovids is Marlon Brando 23 years old, raw and utterly

11:21unpredictable. In Kawaski, their first meeting becomes a razor sharp, dangerously seductive battle of wheels. Every word is a challenge, every silence, a power play on the eve of a streetcar named desire, ambition collides with artistic truth, and neither man is willing to blink. After the legend, before the icon, there was this room. See Kawaski, the electrifying new play by Greg Ostrin, directed by Colin Hanlon, live on stage at Chicago's Looking Glass Theater, one audition to towering talents, a moment that changed everything. Purchase tickets now at LookingGlass Theater dot org. That's LookingGlass Theater dot org. It's not all fun and games, right? There's some serious business to take care of. In October, things are going to be paying attention to, including budget season is really getting heated up this month. We're going to talk a little bit of election coverage as well, but let's start here because

12:21a group of 29 older people have sent a letter to the mayor's office with what I can only call a list of budget demands. What's on that list? And why position it like this? Why show up like this? Yeah, so the council members are basically blitzing the mayor before he has even gotten his budget announcement out. Yeah, so this list of demands came out earlier this week. The mayor is expected to have his budget announcement in October. And I think this speaks to this relationship that this particular council and particular mayor have with each other, which is different than a lot of mayors that we've seen. We've talked about this a lot on the podcast where in the past, Chicago City Council served as a quote unquote rubber stamp city council, whatever the mayor said, they kind of went along with it. That has not been the case with Brennan Johnson. He has gotten opposition from what some people would describe as like the business friendly

13:23or business aligned alters or kind of more moderate or conservative alters that we have. And he's also gotten increasingly pushback from people in the progressive caucus. But what we're seeing with this particular list of demands is more from that kind of moderate business aligned caucus in the city council. And at the top of their list is telling the mayor do not put a head tax in this budget, which to remind you what happened last year, Mayor Johnson pitched a $21 per employee head tax on companies with more than 100 employees. This was his way of trying to get more money to cover the budget hole last year. They got to compromise at one point where it turned into a $33 per employee monthly tax on companies with more than 500 Chicago employees.

14:23So kind of targeting larger businesses. But ultimately that didn't go through as we know last year for the first time in 40 years, city council passed an alternative budget to the mayor's proposed budget. So I think what they're doing this year is digging their heels in and saying, hey, we're going to do that again this year. This budget is going by our rules, not yours. Yeah. I mean, you talk about used to be a rubber stamp for the mayor in terms of budget. If these numbers I'm looking at are correct, you might see a budget vote 11 years ago, 46 to four. We haven't seen 40 orders agree on a budget in the last two administrations. And so in addition to no head tax, something to again, obviously derail last year. The mayor is quick to remind folks, including myself directly that the city council ultimately voted on a budget that was 98% as he likes to put it.

15:24He's original proposal, but some of those big pieces of opposition were things like the head tax, right? They were 98% is pretty generous. If you take out the head tax, that was kind of the mayor's. That was his big solution to solving the deficit. And so in addition to no head tax, that off the table, what were there other demands? Yeah, they also want the mayor to reduce the recurring cost of city government before asking taxpayers to kick in more. What they're referring to in that case is when we had those federal COVID dollars, that's set up a lot of temporary agencies, temporary programs in the city that a lot of people, including the mayor liked. And some people would like to see continue. City council is saying, hey, just because we have this temporarily with federal money doesn't mean we can ask city taxpayers to keep funding that in perpetuity there.

16:27So they're asking him to take a second look at that before there's any new discretionary spending. When they're referencing savings through efficiencies, what does that look like exactly? Because I feel like that comes up every budget season. The mayor's office asking all city departments to find efficiencies, fine cuts. If you're doing that year after year after year, it kind of calls into question, is that a realistic thing or is that just kind of a term that gets thrown around during this time? Yeah, I mean, efficiencies that is another word for cuts or layoffs, right? If you're a job and you hear the boss say, oh, yeah, we need some efficiencies, somebody's getting laid off. So in recent budgets, the mayor has found some savings by saying, hey, there are some vacancies on the books. We can cut those. But eventually, once you cut out those vacancies, then you start getting to city employees.

17:30And so the municipal labor unions don't want to see the city cut municipal employees. So he's going to get some pushback from that. And ultimately, if you cut city employees, then that means that you're cutting some city services eventually. So I think you get in this kind of endless loop of like, okay, city services are going to get worse and taxpayers are going to get frustrated by that. So I think it puts the mayor in a real pickle there. And then their last demand was no reliance on springfield revenues that have not been approved. And that's obviously referring to what CPS did. They approved a budget that relied on springfield, which it might not happen. I'll ask question. Is it safe to say this is mayor Johnson's most important budget of his term? I mean, yeah, because of course, he's running for reelection in the spring. So I think if we see another budget that is led by city council members instead of the

18:35mayor, what does that say about the mayor's power? His ability to lead his ability to solve this over $880 million dollar budget hold that we have. I will say that this recent letter with a list of demands was signed by 29 alderman. That is a large group out of 50, but it is not a veto proof majority. Vito proof majority is 34 alders. So that would mean like if the mayor puts for something and he wants that to get through. And then he tries to veto it, then they would need 34 alders to overturn that. But it's still it's still a pretty large group. So I think the mayor is going to have to find some common ground with these more moderate alders. I don't think going into this election season that we are likely to see anything close to resembling collaboration or compromise. I think this is going to be a long process that makes his way into the winter. And I do think that's ultimately going to be a disadvantage to the mayor going into

19:37a Chicago second election season. But I also think to be fair, we've talked a lot about what's going to be a disadvantage to mayor johnson, what does he have to prove here? I think if the city council members are going to release a list of demands where they say we don't want this, we don't want this, we don't want this. Okay, well, you need to propose some sort of revenue driver here, right? You've already voted. I think it was it was 50 to zero a couple of years ago on no property tax types. You don't want a head tax. The sales tax would have to go through a complicated process of going through springfield. So like that's not really on the table. We haven't heard much about that this year. So your proposals last year to sell off a city debt to raise money isn't necessarily working. They say the mayor and his budget office is slow playing that. But again, it has not yet gone through the licensing video gambling.

20:40Right, those haven't been approved. And so we're not seeing revenue from that. So I agree with you 100% like where are your revenue solutions in this idea that like hey, like follow our demands. And then we will work on you for creative solutions. As a reminder, these people we're going to be voting for as well. Yeah, we also speaking of gambling as well, I think a few years ago, we were relying on the casino to pick in a lot of money that obviously has not happened either. But that also is another problem here. I agree. I'm not hearing long term solutions from either side. And so like you said, I think everyone should be held to criticism at this point. If you're going to buck against the mayor's proposal, then come up with something on your own. We've got an election coming up November 3rd. And so I wanted to remind people of some really important dates to put on their calendar, including one early voting begins at 9 a.m. today at two downtown locations, including

21:43the early voting supersite at 137 South State. And then the Chicago board of election offices at 69 West Washington. That is on the sixth floor. If you have not looked at your sample ballot or haven't thought about this since the primary or maybe you did not vote in the primary, just a quick reminder, all of us are going to be voting for a Senate seat. You're going to be voting for your Congressperson. We're voting for the governor, a list of of county seats, including Cook County board president, a list of state seats like Secretary of State, Attorney General, and then all the way down at the bottom. You're going to have your judges as well as water reclamation district. And so again, if you haven't been tapped in for a while, please go check out a sample ballot. You can type in your address and it'll pull it up for you. I don't have any ballot initiatives that I'll be looking at, but across Chicago, you

22:43may be asked questions about taxing millionaires. You should Illinois be investing billions of dollars into a quantum campus. How should we move forward in regards to gunshot detection technology? And so you may also be asked to vote or or electric position be heard on some referendums, some are binding, some are non binding. So again, looking to that early voting is going to expand across all 50 Chicago awards on October 19th. If you want to vote by mail, your last data request, a ballot is October 29th. And then a reminder, all of us are going to be voting for the first time for a fully elected school board. Next week, I'm going to be sitting down with some great friends to give you a preview on what you should be looking for, what candidates are still in the race for school board president. We are down to just three remaining. Again, this is something that polls have shown a lot of Chicagoans are not aware of. And so, you know, reminder, Chicago school board really sets the agenda for Chicago public

23:51schools. They hire and fire the school super intended. They make decisions as relates to CPS's budget. So whether you have kids in CPS or not, this impacts you deeply. So again, we are going to be talking about elections all month long to make sure that you feel confident and comfortable heading into the booth in your neighborhood, come November 3rd. I was going to say, I think the most interesting election in November is the Chicago school board election. I mean, you mentioned things like voting for Senate, voting for members of Congress and everything. A lot of those select forgone conclusions. I was going to say, I think we all know who we live in Illinois. We live in Chicago. That real election was in March, right? It was the primary. That is kind of the one that is really heated. But with the school board, whenever there is anything happening in the Chicago public schools, I always head over to chalk Beach, Chicago.

24:53They are the experts on this. So if you want to know more about any of the candidates, they have a great guide. I was just looking at it before we started recording on how the incumbents. They voted over the last few years. Unfortunately, there are at least two seats on the board coming up that are unopposed. I know. Including mine. Yeah, and mine as well, Jacobi. I think that speaks to, like you said, many Chicagoans are not tapped into this because I think if they were, you might have more people running. So if you are in an area that actually has a seat that is up for grabs, go look into those candidates because it's really important. Even if you don't have kids in school, CPS affects everybody, right? Because I think ideally, we would like kids to go to good schools and become productive members of society and everything.

25:53So it's important to know what's going on with CPS. As you pointed out, our friend, Rima Amin, wrote up on how the incumbents voted on things like a several closures, superintendent license, CTO contracts, hiring an interim CEO, budget, and more. We are going to be talking to Rima early next week. So again, stay tapped in. Make sure you subscribe to our daily newsletter at Chicago.citycast.fm. We're going to have plenty of election coverage along the way. Before we get out of here, I want to know what are your tips for Chicagoans to make the most of October 2026, Adora. I'm looking at you. Hey, it's back to the marathon full circle. So you know, the Chicago marathon is October 11th and it stretches out 26.2 miles throughout

26:55the city. And so it will likely impact your commute, whether you are someone who's running or you're spectating or you are just trying to get brunch with your friends. You don't really care. You should probably take the CTA on October 11th. But also I have a tip if you're spectating. If you want to really impact the marathon runner themselves, you want to speculate between miles 20 and 23. They're about to lose all hope because that's where like there's not a lot of people there. That's not really a sexy viewing spot. People want to be toward the finish line. They want to be toward the beginning. They want to be at like the after party, which is the 27th mile post race party. But the runner themselves will need your help and need your encouragement miles 20 to 23. Mile 20 is over by 18th and hosted in Pilsen. Mile 21 takes us back across the river to I think near Ping Tom Park. Those are all great spots. Yeah. Mile 22, 23 were now in Bridgeport near Sox Park for 23 and 24.

28:00Yeah. Why am I immediately thinking all of those spots that you named? I'm like, and you can get some good food. Everybody's running and I'm just like, I would be there like spectating like saying I got some tacos. What's going on? What you going to do? Say it in star. I mean, yeah, I'm not going to. I'm not going to go to Chinatown or go. I'm not going to go to Chinatown or go to Pilsen and not get a little snack. I like to ride my bike like a couple blocks away around the perimeter. So I can kind of see different aspects of the race. But I like that. All right. Chicago marathon October 11th. If you want to see the entire course map, get more information head over to Chicago marathon.com. Lee, what is your tip for people this October? So my tip to sort of circle back on the CTA because we just were all about callbacks on the side of the sode. My tip is on Halloween, take the CTA, especially the L. When you're going from party to party, when you're doing whatever, A, you're not going to get hit with like stupid surges from

29:06Lyft and Uber on a Halloween because everybody's going to be out that weekend. And two, my favorite thing is the people watching on the L on Halloween by which I mean the costume watching. Like I just love getting on the train. Like there was this one guy. I was on the red line last year and he went as a lamp. And I think like his friend was a fly or something like it was, you know, like it was like, I don't know. You just see the craziest things. I love it. I love like the sense of community that you see. And so that's, I don't know. That's my tip. And then hopefully you'll hear Jacobi on it. Perfect. Hey, Lee Kirk, so I'm not coming for your job. I am advocating for maybe lane litigate though. But so this, I guess this is less a tip and more me soliciting to the audience to help me. Where should I go in the city to build good costumes? Like I've seen the lists that are out there like, you know, go to the thrift store.

30:14You know, go to another bus, there's a bunch of costume shops in like Anderson Vio. And it was down. So I highly recommend Beatniks on Roscoe. They have great costumes there. They're more like, like that place exists like for drag queens like they're open to like the night. And regularly and they have a crazy amount of wigs. Like if you need wigs and their customer service is excellent too. Like they really wait on you and it's personalized. You don't feel like you're just like walking in somewhere and need to find something on your own. Like they actually give you advice and help you. The basement has a bunch of vintage clothes that are like 80s 90s. So yeah. And I think it may be a so train that potential. I've never been so yeah, I've never really been like full costume. Like I'm a thought a big bird costume on or something. I could do like an error piece, right? And so I'm seeing things like I see lost errors up in Rogers Park.

31:19People saying, Rags stock. Obviously you can go hit like some some some vintage stores. If you want to do a more DIY. But say idea once you go, like just to a straight costume place, get some mass, get some fake blood. Y'all got any suggestions for that? I just I let me tell you about me in Halloween. I think months before because you really do like thrift each piece. Does that make a sense? Yeah. I sound like you you really build it from scratch. We're here to cosplay. Okay. So what's your costume this year? Oh yeah. Oh yeah. So have you seen the show? Avatar of the last airbender. Yeah. Yes, I have. Beautiful. And I my husband is very tall and I'm sure I'm going to be Ang. And he's with the author. Are you? Oh, the big water bison. Yeah, that's amazing. Yeah, I love that. Are you doing a ball? Oh my god. We're not here of like games. Are you going to like? I'm going to get a brown ball cap and then have the like light blue paint on my forehead.

32:30So that's what I'll get from Michaels. We have the yellow orange kind of wind blowing on some. You got your staff already got my glider. What did you get like the actual costume part? Which did you find that different pieces over time at various stores in Chicago? There you go. Okay. I'm going to look out for also shout out to Alyssa who I've mentioned on the pod before. Alyssa, we've got to get our costumes together. Alyssa. Alyssa. Alyssa. Alyssa is supposed to be Lizzie McGuire from the Lizzie McGuire movie. And I'm supposed to go as Isabella. And so I need to find like I'm going to look out for like lime green that kind of like like brats summer green. Okay. And stuff like that. But I don't have lime green shit. So I got to find that. All right. So basically we all we need job list. We need you. We need you. All right. I'm going. I need good places for DIY. I need good places to just like grab something off the shelves.

33:31Please hit us up 7737A02046. I'm going to give a huge thank you to our guests today. Adora Nami got a thank you for making time for us. Thank you for having me. Legion Greco. Thank you for being in the building. Always happy to be here. And for everybody else make sure you are tapped into all city cash Chicago has to offer. And it is quite a lot of you knew around here. We got a daily newsletter. We've got an events calendar. You can sign up to become a city cash Chicago neighbor. You're going to get invites to neighbors only events. Afree listening and so much more. We got our fall membership campaign coming up soon. So if you want to hold out for a couple more days and you sign up to become a city cash Chicago towards the back end of next week, you don't also get our brand new piece of merch. And there may be a classic slogan on the front or something. So let's finish out with some good news. You can come see the city cash Chicago team this weekend at sauce night market in

34:33Pilsen. That's going down October 2nd and 3rd. We are going to be there Saturday amongst 50 artists, makers, small businesses, some great foods, some great cocktails and music. And we'll be handing out freebies Saturday night. We got all the details for you in our show notes. We going to be back bright and early tomorrow. We'll talk to you then. Peace.