The National Climate Prediction Center has released its outlooks for the next few months, and they look mixed for Chicago:
For the summer months of June, July, and August, the outlook for Illinois is [equal chances] for rainfall and an increased chance of being above-normal on temperatures. It is a rare combination in Illinois to have a warmer than normal summer without being drier than normal as well.
For September, October, November, southern Illinois has an increased chance of being drier than normal. This is part of a larger area of drier conditions in the South and Southwest. The rest of Illinois is EC. All of Illinois, and almost all of the US has an increased chance of being warmer than normal in the fall.
I haven't gone back to look at earlier predictions, but I think they've been pretty close this year.