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I believe that the city of Chicago could defray some of the costs of hosting the Olympics by also holding a World’s Fair at the same time, or in the years before or after an Olympics.
The same buildings and construction used for the Olympics could also be used for a fair.
A World’s Fair would draw tourists and business, as well as attention to the city, perhaps more so than the Olympics. World’s Fairs in Chicago have been successful in the past–more so than for other cities in the country.
This is in part due to its central location as a transportation hub.
