IFR. I have never flown IFR into MDW, but I do not think you will get
vectored too badly coming in from the SW. Do expect to get sent lower
(3000), probably as you near the Joliet VOR (JOT) or perhaps further
West. I would probably file to the JOTv, and then expect to get
vectors upon reaching JOT, or perhaps the CGTv.

Thats a hit or miss... when I used to fly around Chicago I'd get direct
bases or I'd get about 30 minutes worth of spacing and landings between
737s.