Re: Chicago area airports
Mark, having a lot of family and business in Chicago, plus Wings of Mercy trips, I reckon I have averaged one trip a month over 11 years, well over 100. A couple of IFR tips for anyone coming to Chicago airports from the east.
If you file to KLOT or any of the others in that area, ATC will often give you Goshen-Peotone-Aurora VORs. Big run-around. File to KGYY, Gary. First, they will usually give you Gipper (GIJ), much better.
Then, if you can go VFR from Gary, cancel IFR, go VFR and keep the squawk. Chicago approach virtually always say OK. If you want IFR, when you get about 20 out from KGYY, request change destination to KLOT (or Clow or Schaumburg or Midway or wherever ...) They will almost always send you to CGT (Chicago Heights) then RV (radar vectors) destination. MUCH faster. I have a nephew who works Chicago approach and I asked him if this bugs them, and he says they couldn't care less.
p.s. if you are ever going to Waukegan, UGN, the same method will save you 25 minutes or more. Otherwise they will take all the around by DuPage (DPA) VOR and often into Wisconsin.