"They expect this to be an industrial city, an old, deteriorating city. They're amazed that this lake or this ocean exists," said Mayor Daley.
On Wednesday, he said he plans to sign a host city bid agreement that would put taxpayers on the hook if the Summer Games go over the limit.
Mayor Daley gave IOC members a glimpse of his city in a small room meant to convey big plans for hosting the Olympic Games. But those plans come with a cost, one the Mayor still promises won't touch taxpayers.
"No, you're not on the hook because it was purposely intended to protect taxpayers," said Daley.
Daley insists a $500 million insurance policy and projected surpluses mean the Games would have to lose more than a billion dollars before taxpayers would have to foot the bill.
"That means everything goes bankrupt in the world. The whole thing collapses in 2016. That's what we're looking at," said Daley.
"This is important for our bid but we will have the city very, very well protected," said Patrick Ryan, Chicago 2016 chairman.
Money is a major motivator for the IOC. They want to be sure they're not left holding the bag, even though IOC members claim the Olympic Games themselves have not lost money in modern times. They don't count cost overruns on what they view as optional city projects.
"I'd say, don't worry about it," said Dick Pound, IOC member, Canada.
"The legacy and what it does for the city, it fast forwards infrastructure in the city maybe 15 years ahead of time and nobody can put a price on the good feel factor," said Patrick Hickey, IOC Member, Ireland.
Rio de Janeiro is telling IOC members it doesn't fear big costs.
"It's not spent, it's an investment in the future. If you look at the three cities, the city that will benefit the most from the Olympic Games is clearly Rio. It's why Rio citizens are willing to pay for that," said Carlos Osorio, Rio 2016 secretary general.
In an exclusive interview, a member of the Evaluation Commission that judges the 2016 cities says Chicago has what it takes.
"At the end of the day, members of the IOC want to award the Games to people they like and have confidence in," said Sir Craig Reedie, IOC Evaluation Commission.
The 2016 competition now enters its final lap. There are just three and a half months to go before IOC members and the leaders of the candidate cities meet again in Copenhagen for a final round of presentations and the vote.