Do you actually like living in Chicago?
I’m 25M and moved to Chicago on November 10, 2025. I’m struggling to adjust to actually living here, even though Chicago has always been my favorite city to visit.
I still have my car, but I rarely use it. The issue isn’t that I can’t afford it, it’s that using it often feels inconvenient and like a waste of money. I mostly stay within the Loop, and I’ve started feeling trapped here. Even simple things like getting groceries feel like a hassle. I don’t want to drive, but I also don’t want to walk or take public transit while carrying groceries.
Back in Missouri, a grocery trip usually took 15–30 minutes total. Here, it can easily take 45–85 minutes depending on traffic, walking, or public transportation. Food delivery has also been frustrating. Back home, I could DoorDash late at night and usually get food within 5–10 minutes. Here, delivery often takes 1–2 hours, and there are fewer late-night options in the Loop. Even things like buying alcohol feel more limited compared to what I was used to.
I genuinely love Chicago for the architecture, things to do, and food scene, but day-to-day life here has felt a lot less practical than I expected. Compared to the smaller town lifestyle I came from, simple tasks feel more inefficient, time consuming, and mentally draining.
I’m conflicted because I still really like the city itself, but I’ve been pretty miserable actually living here. At this point, I’ve even considered moving somewhere like Westlake, Texas, mainly so I could have more space, more privacy, and a quieter day-to-day lifestyle.
The difficult part is that I don’t really want to move to another Chicago neighborhood unless I’m still in the heart of the city. I currently live in the Loop and work about a 4 minute walk from my apartment, which is a huge benefit. Adding even an extra hour of commuting each day would make the move from Missouri feel less worthwhile financially.
Once I factor in the pay difference, commute time, and overall time lost, the move starts to feel less economical than my previous situation if I move to another location further out.
Has anyone else felt this way after moving to Chicago, especially from a smaller town? Did it get better once you adjusted, built a better routine, or found ways to make city living feel less draining? Any suggestions would be appreciated.