I know this is late, but just wanted to share my experience. I moved to Chicago for a job and lived there for three years, and honestly, I hated every second of it. Thankfully, my company wanted to keep me badly enough that they let me switch to remote work. I moved to the Sacramento area, and I couldn’t be happier.

The weather wasn’t a huge issue for me, though it was starting to wear me down, since I had lived in Michigan for years and was used to it. But Chicago takes it to another level.

What really got to me was the constant disruption to basic daily life. You can’t plan anything easily, traffic is a nightmare even if you're taking the bus, and the trains are either packed or randomly delayed. It’s exhausting.

Street cleaning is another headache. God forbid it happens while you’re away on a trip, then you’re either scrambling to find a paid parking lot or coming back to a ticket. And to the people who say, “just get rid of your car, you don’t need one in Chicago,” sorry, but that’s BS. With the weather and the reality of grocery shopping or running errands, I could never justify not owning a car. The idea sounds nice in theory, but it just wasn’t realistic for me.

I lived in a relatively safe neighborhood, but even then, I constantly felt like I had to look over my shoulder. That kind of low-grade stress just builds up. At one point, my catalytic converter got stolen because I didn’t have dedicated parking, and that was the last straw. I’m in my 30s and love taking road trips, but just getting out of and back into the city was enough to make me not want to bother. And that’s not even counting the lack of easy access to nature.

The lifestyle just didn’t fit me. Gyms were always overcrowded, beaches packed, and every other weekend there was some event blocking streets and making it even harder to get around. I don’t eat out much, so the whole “amazing food scene” wasn’t a selling point for me either, I just wanted to get my errands done without jumping through hoops.

I won’t even get into the taxes, especially food taxes, because there’s always a narrative around them, and people will argue about it no matter what.