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Madrid would be the best choice. The other three are horrible.
Chicago... eh. I went to college there and couldn't imagine what it could really offer, though I'm sure the city would be excited as it would give them further chances to renovate.
I don't know the full inventory, but there are quite a few outdoor arenas already, a bunch of indoor sites with the universities and wherever it is the Bulls play, and a great venue for the sailing events.
The Olympics in Chicago would be a horrible event. The city is entirely unsuited to the task. The proposed venues are extremely far apart and Chicago's mass transit is in tatters from the decades of neglect. Daley is a ************* too.