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I rank San Francisco's, Portland's and Washington D.C.'s system as better than Chicago of systems' I've been on. New York's I think goes to more places and tourist hot spots than Chicago's.
Chicago's is better than St. Louis's due to its size and I can't think of any other system I've been on, I was really too young to remember Bostons. Boston-Chicago-NYC are obviously some of the oldest systems in the country as well.
I don't know anything about Portland's, but from what I've read, San Francisco, DC and NYC have better systems. Philadelphia also comes up a lot when people are talking about good mass transit.
But when you compare the CTA to the systems in Atlanta, Houston, LA or most other major metros, it's way better. And that says nothing about suburbs and smaller cities where it really doesn't exist. Chicago's in the top-10 and that's out of hundreds of other cities.