The last time I flew to DPA I filed CGT JOT. I was given GIJ OXI EON
on the way by Chicago Center's request - not as good. Once I passed
OXI, though, I got direct DPA.

When flying through Chicago Approach's space, be ready to write and
take new directions, and follow them, and they'll take excellent care
of you.

Every time I've flown through there, they've been super accomodating.
I usually file a route that obviously tries to stay away from their
heavy traffic, but regularly get updated routes direct though Midway's
space or vectors through O'Hare's. A few weeks ago, flying from DKB to
the east, I filed JOT CGT direct. They gave me direct JOT through
Midway's Class C quickly. Then the controller asked to confirm I was
just trying to avoid the lake (it didn't show up in my remarks). I
told him yes, and he gave me a turn towards the shore, visual along the
shoreline, then direct. It couldn't have been better.