Leaving aside the question of whether or not Chicago should have pursued the 2016 Olympics in the first place, on a purely political level, maybe President Obama got lucky that the city wasn't selected.
First, if Chicago had been selected, there wouldn't have been the spectacle of conservative pundits celebrating America not getting the Olympics shines a spotlight on the petty, hateful nature of his political opposition.
Second, you can bet your bottom dollar that if Chicago had been selected, the 2016 Olympics would have been turned into ACORN all over again, with James O'Keefe running sting after sting.
Instead, Chicago didn't win out. Compared to eight years of failure on the economy, Iraq, and Afghanistan, it was a pretty small defeat. In the end, the most memorable thing about it will be the partisan, mean-spirited response by the American right.