Here is my experience on a EWR-MDW flight:
Got to EWR Term A early expecting some sort of delay. Checked in at the kisok (no line), went to present my id to a CO staffer, who told me it would be checked at the gate. Had my ticket & ID checked prior to walking down the passageway to gate 26--all went smoothly. No problem or delays at the luggage scanner (I had one small briefcase as a carry on + a purse). In the PC, I again asked about having my e ticket 'initialed'--"at the gate" again I was told. At boarding time, CO did mention that ID's would be checked and random bag searches could be expected. As I was in FC, they boarded us first and I didn't get to see if they did seach anyone. We left on time, so all in all much smoother than I expected (or experienced prior to 9/11th).
No problem for deplanning at MDW--BUT be warned as I was leaving the terminal for the CTA at the exit for the trains/garage the lines were very very long. It seems that passengers departing on flights from MDW have to display tickets & ID prior to entering the main terminal and it looked like there were only 3 or 4 security personal staffing the desks--this at 2 pm on a Sunday afternoon. The lines streched into the parking area and I did notice lots of people apparently taken unaware of this delay development.
I leave on a 7am flight back to EWR on Tues, hopefully things will be easier at that time, but just in case I will add in some extra time.