ORD commuter here. Do it all the time on company. M-Th nights, there are 4 ORD-SDF non stops, 1 to PHL, 1 to DFW. On Fr night, you are down to 2 or 3 SDF nonstops, none to PHL or DFW. Tails are normally: 1 MD, 1 767, 2 A300’s. Usually plenty of seats. Gateway parking is plentiful, no pass needed. If going out on a 14 day trip, I would usually mention it to a gateway manager, but that was under the older parking lots and construction.