About a month ago I was in Chicago with my sister. Chicago was fantastic, I was really impressed. The architecture was beautiful and the tour we took told the fascinating story of how the architecture are intertwined with the history of the city. The city overall is gorgeous, full of trees and surrounded by water on all sides.
Coming from NYC, I was impressed by how clean and well-maintained the city is, and by how cheap and effective the transit there was. Nominally, it's a bit less convenient, because you have to walk further, but in practice it's much better, because it's not super-crowded and breaking down all the time like the MTA.
Chicago was also cheap, in the way that non-coastal parts of America are cheap, but also had a lot of great unique culture, including art and food.
The thing that really surprised me about Chicago is that it's also a beach city, with the gorgeous azure waters of Lake Michigan lining beaches that run all along the East side of the city.