I like Buffalo’s flag.
I’ve searched and searched and I guess my city doesn’t have an official flag. I did find this Franco-American flag, which I think is kinda nifty.
Holy smokes. Well, if that’s still Buffalo’s flag, I still like it. So, there. 
Another interesting about Pittsburgh’s flag is that it incorporates the city colors of black and gold. Nothing remarkable there, of course, until you consider that the Pittsburgh Steelers, Pittsburgh Pirates and Pittsburgh Penguins all use these as their team colors.
This is the only city in America where this happens.
I think Boise’s flag should rank higher than it does (114). Yes, it bears the city’s name as do many of the other low-ranking ones, but it’s toned down, not in-your-face like the one for Provo. The one for Pocatello (dead last) is embarrassingly bad.
My favorite is the one for Denver’s and its mountain/snow/sun motif.
I don’t think the one for Des Moines is all that great for where it’s ranked. What are those humps supposed to represent anyway? Haystacks? Corn kernels? People’s heads? Bridge arcs? Boobs?
Cedar Rapids, IA looks like a postcard you’d find on a discount rack.
I agree the Chicago flag looks “off” in the picture. And you see that flag everywhere in Chicago.
I think my favorite is Cheyenne, WY. Not very often you see the color brown utilized in flag design.
FYI, here are two (sometimes contradictory) views of what makes good and bad design in flags:
North American Vexillological Association.
Josh Parson’s Grading of National Flags.
Notably, both agree that:
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The design should be simple. No seals.
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No writing on flags.
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Colors should be selected carefully and their number limited.
It’s a relatively safe bet that Parsons would hate, hate, hate all but a handful of the city flags, and only slightly more of the U.S. State Flags (scroll down).
Based on that link, I think it’s obvious that the flag was designed by their Webmaster. He/she should be taken out an shot.