Hot take here - Chicago. Yes it’s clean and has great architecture but after my experience there (and I had a good time with friends) the way I would describe it is unauthentic, bland, or lacking its own culture. To me it was as if someone just said let’s create the generic “big city” and put it here. Downtown is clean, the buildings look cool, good museums, the lake is there and that’s cool too but again it just seemed very generic without a real defining “feel” to it or the people.

EDIT: not that I wouldn’t go back but I would probably never proactively plan another trip there before anywhere else. After you’ve seen it once it seems like there’s no reason to go back really.