Other than Chicago for the Midwest:
Large- Minneapolis(Twin Cities), Saint Louis, Indianapolis, Milwaukee, Cincinnati. I guess I may be open to Detroit and Cleveland as well, if I could explore those metro areas more? I suspect Kansas City would also be nice too, but that's one of the few bigger Midwest metros I've never quite gotten to visit. Same with Columbus, OH, as well.
Medium- Madison, WI, Bloomington-Normal(IL), Champaign-Urbana(IL), Bloomington(IN), Iowa City(IA), Kalamazoo(MI), Grand Rapids, MI, La Crosse(WI). I suspect Des Moines and Omaha would be nice as well, but I haven't yet been able to do a proper trip to those places. Duluth(MN) would be another option, IF I could learn how to handle the extreme cold in their winters up there! Columbia(MO) and Ames(IA) I'm sure also would be nice, but I hadn't visited either of those places.
Small- Traverse City(MI, on a side note I wish that passenger train proposal between Traverse City and Ann Arbor could become a reality! here's the proposal some rail advocates want MDOT to consider starting as a new passenger train service:
https://a2tc.org/ ), Madison(IN), Mackinac Island, MI(dunno what jobs one could apply for here, besides lol if you were to work at The Grand Hotel or work at one of the other seasonal tourist businesses). Ashland and Eagle River also look nice, for small towns in northern Wisconsin IF I was up for getting used to living what there would likely be like(i.e. having to buy a lot of things online, and/or likely having to drive a few hours for bigger shopping trips). Can't forget Yellow Springs(OH), that town also looked really charming when years ago I visited Antioch College(or is it University? I can't remember) there. Also when I took the Amtrak Empire Builder through this town, plus on my own later google street viewed it, Red Wing(MN, Amtrak has a stop here) and Hastings(MN, Amtrak doesn't stop here but the train passes through the town) both look like they'd be pretty charming towns. And from the one time I google street viewed it, Stillwater(MN) looks very charming as well.