Observations from a weekend in Chicago:
Wrigley Field isn't nearly as nice as Fenway Park in Boston when you compare the game's two old ballparks. Wrigley is desperate for a modern scoreboard which they should place in centrfield and tear down that old thing that is there now. Half the crowd at Saturday's Cubs game against St. Louis consisted of Cardinals' fans draped in red. The Cubs are awful-- they won the last two games of the series but they have no stars.
Even though Chicago is a vibrant city you need a special constitution to live amongst all of those high rise buildings. The Trump Tower is gorgeous and there are so many huge skyscrapers there. I hadn't been to Wrigley since I was a kid and what a place-- right in the middle of neighborhoods with no infra structure to help with traffic, etc. There were 41,000 at the game and the el trains were jammed heading out-- most people don't drive and park at Cubs games-- $50 to park if you can find a place.
Chicago is fun and fun to visit. But living there, I don't know.