My Landlord Sent Me a Number and I Haven't Been the Same Since

By Jay Kimbol · June 15, 2025 · More posts

I've been in Chicago six years. I moved here from Rockford thinking I was making the big move, the real one, the one that meant something. Got a one-bedroom in Logan Square for $1,640 a month back in 2019 and thought I was basically getting away with something. My friends in New York looked at me with genuine envy.

That was then.

Last Tuesday I got the lease renewal. I've been doing this long enough to know you don't open lease renewals at work, because there's a real chance you'll make a face and someone will ask you about it and you'll have to explain that yes, $2,390 a month is indeed what they want now, that's not a typo, that is nine thousand dollars more per year than what I paid when I moved in, and no I don't know what happened to Logan Square either, it used to have that taqueria.

For context: I do remote IT support. I've been at the same company for four years — good job, stable, work from my apartment in my socks, and I make $71,000 a year. That sounds fine until you run the actual numbers. After Illinois state tax, city tax (yes Chicago has its own income tax on top of the state, never let anyone forget that), and federal, I'm taking home around $52,000. That's $4,333 a month.

Rent is now $2,390. That's 55% of my take-home. I know the rule is supposed to be 30%. I also know that 30% of my take-home is $1,300, and there is no apartment in Chicago for $1,300 a month that I would actually live in. So the 30% rule is a thing people say, and then they pay 50% and try not to do the math too often.

I sat with the lease renewal for about three days before I did what I always do when I don't want to make a decision: I started researching instead of deciding. This is a character flaw I've made peace with.

I started with the usual stuff. Cost of living calculators. Most of them are kind of useless — they tell you that yes, San Francisco is more expensive than Memphis, a thing I already knew. What I actually wanted to know was something more specific: if I kept my exact job and my exact salary, what would my life look like in a different city? Not "is it cheaper?" but "would I actually be better off?"

I eventually found a tool called shouldimoveapp.com that does something closer to what I was looking for. You pick two cities, pick your job, and it estimates what that job typically pays in each market and shows you a purchasing power comparison. The salary estimates aren't perfect — nothing like this is — but the purchasing power framing is what got me. It's not just "rent is cheaper in Omaha." It's showing you that a dollar goes further there, and by how much.

I typed in IT Support, which is close enough to what I do. Chicago to Indianapolis. I don't have any particular feelings about Indianapolis. That's sort of the point.

The comparison showed that a mid-level IT support worker in Indianapolis makes roughly $56,000 — so about $15,000 less than I make — but the cost of living index there is around 95 versus Chicago's 117. When you actually do the math on what your salary buys you rather than just what the number says, someone in my position could theoretically have similar or better purchasing power in Indy even with a lower salary. If I kept my Chicago salary, which I could as a remote worker, the difference gets more significant.

I want to be careful here because I know this is the part where people say "okay but have you been to Indianapolis?" and fair enough, I haven't. I'm not saying I'm moving to Indianapolis. I looked at a dozen cities that night and Indianapolis just happened to be one I could type without googling how to spell it.

The list of cities I looked at included Omaha, Tulsa, Columbus, Raleigh, and Kansas City. Some of them surprised me. Kansas City, for instance, comes in with a cost of living index in the low 90s — significantly below the national average — and has an actual food scene, actual sports, actual stuff to do. Raleigh is on the more expensive end of the "cheaper than Chicago" spectrum but has the Research Triangle thing going on, which matters if I ever want to change careers.

Here's where I landed after three days of research and zero decisions: the math is real. That part is not my imagination. If you make decent money remotely and you're in a high cost-of-living city, there is a version of your life where you make the same amount of money and actually have some left over at the end of the month. I have not had that feeling in Chicago since probably 2021.

Whether I actually do it is a different question. I've lived here six years. I know where everything is. I have friends here, or I have people who have become friends by proximity and I'm not sure I'd stay in touch if we weren't within two miles of each other, which is its own uncomfortable thing to think about.

But the lease is up in September. So I have a few months to figure out if I'm the kind of person who does something about a problem or the kind who just reads about it.

Probably I'll write a blog about it.

Jay Kimbol writes about money, remote work, and the slow realization that the Midwest is actually pretty big. He's based in Chicago, for now. Read the next post: I Went to Austin for a Long Weekend. Here's What I Actually Found.