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90/94/290 and LSD in Chicago.
One of the worst examples of unintended consequences of the freeway revolt (see also I-710 in Pasadena). The system was designed to function as a whole. Instead, by only building out 3/4 of it and then giving up before building a ring interstate, you've got an inefficient system where for millions of people trying to move around the city the only way to do so is to go all the way downtown. It's the same issue for freight as well. And now the city can't even cut back on LSD because it's become so necessary owing to the lack of the planned Crosstown connector.
