I like the Milwaukee flag too; it grows on you after a while. It's like the kid wearing stripes and plaids and polka dots and mismatched socks and light-up shoes of city flags - it's not going to win any design awards, but you've still got to respect it for rocking its own style. I tried to buy one at one point, but discovered that nobody is producing them commercially - the ones owned by the city look like they are all sewn by hand.

Cutting down on the number of elements to make a less cluttered wouldn't be terrible, though. One thing the author didn't mention that makes the Chicago flag so great is that it's easy for citizens and citizen groups to riff on; between that star and the line of four graphic elements between the blue stripes, the entire city's got a common graphic identity that everyone can share.