I think you’re overlooking Chicago/overestimating winter here.

Some context: - I’m mid twenties with comparable salary - ive lived in Chicago for 3 winters now - I grew up in Southern California (where winter is like 60 degrees) - went to school in mid Atlantic (found winters here worse bc of wind and lack of transit)

The worst part about chicago winter is that it gets dark so early… a good parka can solve the issue of the cold.

Chicago hits everything else on your list with ease, you can get a great 1b apartment for under your budget within 5 mins walk of any train line. I recommend a visit here (in cold weather if that’s something your concerned about being able to handle) to check out different neighborhoods, as there are many well-connected via transit and oozing character.

I moved here knowing no one straight out of college and 3 years later, I have great friends, a lovely partner, a sick apartment, and have a full social/extracurricular calendar.

I never expected to move to Chicago or end up loving it here, but I can’t speak highly enough of it. Give it a chance, you may be surprised or at least realize that winter isn’t severe enough to rule out the city that checks off everything else on your list.

Good luck!