Really, comparing Milwaukee to Chicago is like comparing Psy to Barbara Streisand. Just isn't any common ground.
Chicago is a real city; make no mistake about it. Milwaukee is like an old dog you think you should put to sleep, but it's been around for so long, you can't bring yourself to do it. Despite it's attempts, Milwaukee remains a very boring place filled with turduckens.
Chicago is vibrant; always something happening, always people out and about, always an amazing experience, whether you live there or just visit.
Granted, the crime rate is high in Chicago; poverty always begets crime, and there are large numbers of very poor people in Chicago; well, nearby. Chicago has become so trendy that bad neighborhoods are torn down and expensive condos take their place. Not exactly a good answer or a realistic approach to curing the ills of any great metropolis. An old housing project near Chinatown has been converted to expensive apartments. Sheesh.
Still, you can get anywhere in Chicago cheaply, be it cab, bus or subway. There are so many restaurant choices, you get full reading all the reviews. The museums are supreme. We ate at the top of the John Hancock building, on a clear night, so the views were simply awesome. I always go to the Art Institute to visit my favorite Jackson Pollack painting, and of course, get awed in roomful after roomful of impressionist art.
People are by far better looking in Chicago, and nicer. We left Chicago about 4 p.m. on a Sunday night. Thousands of people streaming down the major streets. We arrived back in Milwaukee about 6 p.m. and it looked like a ghost town. It is a ghost town, by comparison. I wish I could tell you what happened here, but I've no clue. Milwaukee just lost whatever it is that makes a city great. Sad. Sad that I live here. But oh so great that Chicago is just right down the road.