Pulling into the Midway ramp with 1994-96 traffic. Private Jet was flying a few MD-80s and DC-9-50s at the time had one in the full livery of Air Liberte being used to fly to SFO and I think MIA, imagine how random it was in the days before the internet to just walk up to the gate and see a French MD-80 sitting there to take you to Chicago. AirLA had just taken over Capitol Airlines and started flights from MDW to MKE and STP(yes, not MSP lol). Kiwi International and Valujet both had a focus city with a handful of routes from MDW, and it was the home of ATA/Chicago Express. Meanwhile in 2017 "Southwest, Southwest, Southwest, Delta, Southwest...". Learn a lot from flying around in these different eras.
Side note for the thread, this screenshot from Prepar3Dv3, which was the last 32-bit sim from the Microsoft/Lockheed line. Since switching to v4 which is 64-bit, this Captain Sim 757 I bought and some of the AI models in the background don't work anymore and need a conversion that the authors may or may not do. For this reason, I say to anyone who wants to buy Prepar3D, do some research on any add-ons you want to buy and see if they are even compatible. I almost regret deleting the game when I upgraded.