It appears that you highly value the large city aspect of Chicago. MCW is west of Milwaukee in Wauwatosa, which is NOT a large city (although you could like 15-30 minutes, depending on traffic, in Milwaukee if you wanted).
Your pros/cons appear to lead you to Rush. The prices of apartments in Wauwatosa and Milwaukee run similar to Chicago/what you posted here.
This was the post I needed. Thank you. Your response resonated with me so much. Every line. Tbh I almost never cry and I haven't but I'm on the verge of being emotional at this second. This was one of the toughest decisions I've ever made. It was so hard. I withdrew from one of them a minute ago (and the others earlier this morning). It's 11:59 PM in both Chicago and Milwaukee right now.
DM'ing you probably tomorrow.