McCormick or vicinity of UC are probably the best bets, IMHO. Probably the closest sites to downtown where a casino could realistically be built, and best suited to anchor an entertainment district (extending existing Madison St bar district further west for the United Center plan, linking up with existing planned entertainment district by DePaul Arena on Michigan/Cermak for McCormick plan), which the city has gone on record saying they want. Both have excellent access to transit as well.
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"Eventually, I think Chicago will be the most beautiful great city left in the world." -Frank Lloyd Wright
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