While Chicago may technically be located in a flyover part of the country, I don’t really consider it a flyover destination/city.
Seems to be more of an island in the midst of classic flyover country. Most things are polar opposites within and outside of the metro area, along with the rest of the region.
Madison, Wisconsin.
I guess I agree with you. While located in Illinois (textbook flyover land), the sentiment of the term “flyover country” is that nobody wants to go there, and just flies over it on their way to some place important. Chicago is out of alignment with that sentiment.
Non-Chicago answer: Denver.
The Wikipedia article that defines “flyover” excludes Texas, New Mexico, Wisconsin, Michigan, Minnesota & all of the Deep South. So: Mostly all those rectangular states in the middle.
Myself, I’d love to spend more time in Chicago. And I’m sure there are other cities in that region worth a visit.
But I’m a Texan. What do I know?
Des Moines is fine these days (a lot has changed in recent years, and it’s shaping up to be quite tolerable), by my heart belongs to Madison, WI.
Denver’s not bad either.
Denver (seconded or thirded).
Madison sounds neat. I spent my undergrad days in Ann Arbor, which I imagine has much the same vibe.
As a longtime Ames resident, I honestly don’t see much in Des Moines. I was caught there for an afternoon this fall with nothing to do - and didn’t find anything I cared to do. YMMV, natch.
Madison is a cool town.
Hate Chicago, but like the Twin Cities. I like the Mayberry feel of the Twin Cities and find Chicago to be far too urban.
Denver. Because I live here 
I kinda like Cleveland.
East Lansing.
I have spent time in Chicago and don’t see the appeal except the Straight Dope is based there. I have a special hatred for Chicago architecture and Frank Lloyd Wright in particular and I do not approve of most Chicago style food.
That said, I do like the more rural Midwest. I used to work a week a month in Indiana and found it refreshing. Those giant corn fields flanked by super straight, flat roads were cool to drive down and the people were nice. I like Oklahoma too. Sure, it gets a little boring driving down the road sometimes but then you have to realize that that God can call you home at any moment via a tornado and it keeps you on your toes. Driving around the Midwest is cool. Besides Chicago, you don’t get many huge skyscrapers or world class museums but those are a dime a dozen. In the rural Midwest, you could take a side road and stumble across the world’s second biggest ball of twine by accident.
Ha ha ha. That is terrific.
If Chicago doesn’t “count”, I spent three years living in Ann Arbor. It’s pretty cool. There’s a surprisingly large amount of stuff to do there, because of the university. Saturdays in the fall are a nightmare, though.
yeah, I’m still waiting for a good explanation for the “Chicago-style hot dog.”
I lived in Omaha for 3 years and Wichita for 5. Both were nice enough but I won’t be rushing back to either.
Bah. It’s a sprawling city in a grid pattern with a lot of trees* and few tall buildings apart from the State Capitol. There are also a few too many malls. But the people are generally nice, it’s got a couple of universities and a big arts center, there are some excellent restaurants, and if you’re into sports there’s Nebraska football and a decent minor-league baseball team.
It’s not New York-style urbanity but there’s a quarter of a million people living there.
*Nebraska is the home of Arbor Day. After a few hundred miles of grassland someone finally said “This place needs some damn trees.” So they planted some.
I’d vote for Memphis, but that may be a bit too Southern to qualify.