I live in the Chicago suburbs, and on the whole I really enjoy it.
Upsides--
1.) Centrally located in US. Nearly everything is a reasonable plane flight away, and flights are plentiful and usually affordably priced.
2.) Four distinct seasons.
3.) All the amenities of a major metropolitan area (culture, business, infrastructure, excellent medical facilities, universities, etc.)
4.) A diversified economy that is holding up reasonably well.
5.) Beautiful architecture, both downtown and in many suburbs.
6.) Faily low risk of natural disaster--we don't really get hurricanes or major earthquakes or wildfires.
7.) Da Bears
8.) The area is quite affordable for what you get. A nice house in a good suburb with decent schools can still be had for around 250k. You get all the pluses of big-city living without the sky-high costs you find on the coasts.
9.) A wonderful Chicagoland spirit. We're practical, unaffected, and pretty friendly, but still sophisticated enough to hold our own with anyone.
Downsides--
1.) Traffic! It's really congested here. Rush hour can turn a 30 minute drive into at least 2 hours.
2.) The summers are hot, the winters are cold. The two weeks between each is lovely, though.

3.) Colorful local and state government. You may have heard of our former governer?
4.) The neighbors are pretty sleepy. Nothing against Wisconsin, Indiana, or Iowa--I like them all and have had plenty of fun there. But it's not like living in NYC where you could drive to a million fascinating places or LA where you could drive to Vegas or catch a cruise in Long Beach. You either have to fly or road trip to get to many tourist destinations.