I can't speak for Chicago, but Summer 2014 in New York has thus far been the coolest I can remember (which is more than three decades).
I recall perhaps two or three other bearable summers—I'd draw the line a bit short of
cool—but none recently (there was one year in the sixties when there wasn't a single 90-degree day). I wish I were well enough to appreciate this one.
A year or two ago we had a goodly number of 100+ days... and, as I'm sure Frances, Claudel and some of the other New Yorkers here can attest, 100 degrees in filthy, muggy New York City is hellish.
Truer words were never spoken.