Portland, San Diego are really nice cities, if I had to chose a city in the Midwest, it would be Indianapolis because I've heard it's a really clean and isn't a dump at all. San Antonio seems like a sick city in Texas lol.
Indy's a nice convention city. Compact downtown, basically all the stuff you'd wanna do in a short stay is within walking distance. And yeah I guess it's clean. There's a reason they have so many big sporting events there. Say you're there for the Final Four, or a business convention, whatever, you basically don't have to go past about four city blocks.
If you wanna hit it up for something like that, Final 4, Indy 500, Super Bowl, whatever, it's set up great. For doing actual touristy stuff, nah.
Seeing the (normal amount) of NYC bashing on the other board i decided to move in the opposite direction - nice cities to visit and chill in. I have a lot of cities i like but I thought i'd mention one i think it less traveled to, Vienna.
Vienna is FREAKING awesome. The food is awesome, the people are very very nice (it's a very relaxed place, at least where i went). it was gorgeous, the architecture is fantatic, the gardens were great, and sitting in the plaza drinking coffee and chilling with my friends there was wonderful.
yeah vienna is awesome, actually every big city in austria(there aren't many)
is pretty cool to chill in, lots of great parks and coffee shops, people are nice and it's easy to get some weed