Or am I just pro Chicago?
The Olympics are virtually always money-losers for the host city. Even for cities that claim to have surpluses:
With frequent overruns, few cities end up recouping any profits after the athletes have gone home. Even cities that cite surpluses, such as 1984 host Los Angeles and 1998 host Calgary, often don't include total expenditures in security and indirect costs in the final tally. And other cities find themselves far in the red. Montreal, host of the 1976 Summer Games, only finished paying off its Olympic debt in 2006. Officials in Nagano, Japan, spent so much on the 1998 Winter Games that they destroyed their financial records.
The cities lose money for the same reason publicly funded stadiums lose money: They mostly pull money from existing entertainment options and spread it around to other sources, causing no net gain. And when you factor in the humongous amount of resources that get sucked out of the economy to gold-plate velodromes and whatnot, well, good luck breaking even, much less turning a buck on the whole thing. Some supporters talk about "The Olympic Effect," the idea that being will to pour money down a rathole shows the world your city is ready to be a big-time playa. Well, maybe, but Chicago is doing far better than average right now and hardly needs that sort of publicity.
Here's hoping the famously corrupt International Olympic Committee "awards" the games to a place that won't bankrupt Americans.
Update: It ain't Chicago. It's Rio.