UPDATE: I took the trip, here's my data
I did fly into, and a bit later, out of, Midway Airport. I had my firearm locked in a hard case from Life Jacket inside my soft-sided suitcase.
On arrival, I just picked up my suitcase from the baggage claim, transported via shuttle bus to the rental car center, got my rental car and immediately high-tailed it to the south end of Lake Michigan and on into Indiana and Michigan, leaving my firearm in the suitcase until I entered Indiana. No problems anywhere, and since both Indiana and Michigan have CWP reciprocity with my home state, I felt very comfortable once out of Illinois.
I was a bit more concerned about coming back into Illinois/Chicago/Midway and declaring a locked/cased firearm. But once again I had no problem other than the fact that the new-ish airline agent at the counter seemed unfamiliar with the process; she got help from another agent, I was soon on my way to the special TSA area for those declaring firearms. (that's a whole 'nuther story about "security theatre", but there was no problem getting it declared and checked through the TSA process.)
Overall, recommend allowing an additional ten minutes at check-in, at any airport, not just Midway. Cost no extra time at the baggage claim on landing, as expected.
Thanks everyone for offering your perspective and experiences!
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