If you don't want to deal with long ORD layover, could also do redeye to IAH, then several IAH-ORD flights available.
edit: Actually if paying for a hotel is acceptable, I would take the afternoon SMF-ORD flight the day before. Plenty of time to stay in a hotel near the airport or get to one in the city. The fewer number of stops, less opportunity for something to go wrong.
Last edited by aau; Sep 25, 2022 at 11:22 pm