Best places in the midwest

Minneapolis is great, I'm from Duluth, MN and it's pretty easy to get along there just a bit out of the way for other cities and cold as balls this time of year. Milwaukee is very cool as well, the Cream City Collective in River west is a cool place to meet and connect. But a lot of the smaller towns can be very fun and helpful in regards to traveling. If you come to Minnesota let me know, I'll be in the area 'til about March...
 
Milwaukee is a great town (also not far from Madison), never been to KC but always heard great things about it, Duluth/Superior is very beautiful, The Upper Peninsula of Michigan will blow you away if you are into natural beauty and woodsy things (I can point you in the right direction of some great spots there), Detroit is always a great time, Ann Arbor (although it seems a lot of kids have left town over the last year, its still pretty much the destination for kids travelling through MI.
 
Best cities:
1. Chicago
2. St. Louis
3. Detroit
4. Minneapolis
5. Cincinnati

Best college towns:
1. Lawrence, KS
2. Winona, MN
3. Bloomington, IN
4. Madison, WI
5. Champaign-Urbana, IL
 
Milwaukee is probably my favorite city in the summer. I don't know if there is a week without some type of festival, and the music venues always have someone good. Also, don't forget to check out the lineups for summerfest, which is an 11 day music festival.

Madison is a close runner up. It features beautiful lakes with plenty of beaches. Mad-town is also a runner up to Milwaukee when it comes to festivals and music.

Chicago is alright. It has everything you could want, and it is easy to get around via the L or Metra.

Kansas CIty seemed alright, but I wasn't there very long.

Inianapolis.....meh