I don't believe that Americans as a whole are upset about "losing" the Olympics. I'm sure the people of Chicago are disappointed. Most people are probably disappointed. Any time you can bring an event that large to an American city, it is good for the local and national economies.
What I think most people are upset about is the fact that, not only, did the President, himself, make the trip (instead of delegating authority) but the amount of money spent on the trip. The President flew in for a short period of time, made his argument in our favor, and then left before the vote even took place. Had he sent someone else, I'm sure overall cost would have been much lower, and more time could have been spent there. I for one am much more concerned about Iran, and the way the President has handled the situation from day one. That, however, is an entirely different conversation.