Chicago is the third largest city in the US. The metro area has over 10 million people. Chicago is very similar to New York.
We are on the shore of Lake Michigan and the city has the tallest buildings in the US. You may have heard of some of them? The Sears Tower? (Now Willis) John Hancock buildings? We have a public zoo that is on the lake shore--Lincoln Park Zoo. Navy Pier. The Planitarium, Field Museum, Art Institute--I could go on, but, there is so much to see and do just in the downtown area, one week would not be enough.
Chicago has Chinatown, Greektown, Koreatown, Rush Street area for major partying, the Magnificant Mile for shopping, State Street for all kinds of stuff. Water Tower for shopping, eating, and more.
The Olympics were to be held all within 10 minutes of the lake shore. The land was already purchased by the city and was an old hospital site. Which would have been the main site. The other sites would have been park district sites. The city has lots of parks and pools, etc.
As for unions and patronage, that is the Chicago way now. That would not change. But, people who are now unemployed and on welfare would at least be working and earning a living rather than sitting on their butts. The contractors and their politician buddies would still be lining their pockets. Just like now. Snow removal comes to mind.