I’ll begin by prefacing this with a mention that I live in the exurbs and work in the 'burbs, so this is more about the 'burbs than Chicago proper. And even if Chicago has the same problem, the grid system makes it easier to avoid the problem areas (or just take transit and not worry about it, which is what I usually do in my frequent trips to the city). Also, seeing as how Chicago is only one city, coordination is probably easier to pull off.
My daily commute goes from Palatine to the west side of the Fox River. Right now every state/federal road that is a major crossing point across the river that is remotely close to routes for getting between home and work (i.e. 72/Higgins, U.S. 14/Northwest Highway, 62/Algonquin) is under construction on the east side. And the couple of smaller crossing, feed off those three anyway, so inevitably unless one takes I-90/Northwest Tollway (which, surprisingly enough, is not under construction), one can expect to be encountering a parking lot. (And while 90 isn’t a terrible route, I have a bit of an issue with adding 10 miles or so to my commute and paying for the privilege to do so.)
So why does this happen?
One theory I’ve heard has to do with securing funds for the construction. Apparently some routes are easier to secure funds for in the beginning of the season, so those projects are taken care of in the spring and summer. And because the funds are secured early, it’s possible to stagger where things are so you don’t create a giant stranglehold on traffic flow. However, by fall, all the projects slated for that years construction budget that haven’t been started yet and finally got the funds all have to be pushed through and completed by the end of the year. That, coupled with the fact that getting the various communities to actually coordinate their construction efforts is like herding cats, leads to the mess that anyone who lives west of the Fox River is currently encountering.