Underrated city. Blue-collar, hard working, friendly people. America's leading beer producer. Home to the greatest music festival ever. Has an awesome zoo, and a true architectural masterpiece in Milwaukee Art Museum. Incredibly, though leaky, ballpark, housing a team on the rise.
Sadly, there's not a lot to do in Milwaukee in winter. But in summer, it's awesome. I said so in the first paragraph above. Plus, there are some hot, nearly topless chicks everywhere.
Chicagoan 1: I'm bored. Let's go get drunk and have the time of our lives!