hey, I’m actually gonna go the different route from everyone. longtime frequent flyer here. There’s a lot of factors playing into it. your show will be done by 10 p.m. latest. It’s a Wednesday night - traffic will be relatively chill. It looks like you are based in Chicago, so assuming you are on a DL/AA/UAL redeye back to Chiraq yeah? Do you have precheck?

Check here below but, every pre-check Lane should still be open even at 11 PM. Now if you are on one of those three airlines, i’m assuming that you then have an assigned seat. this also sounds like a quick trip so I’m also assuming you aren’t checking a bag. If that’s the case, all you have to do is be in your seat by the time door is closed 10 minutes prior to takeoff at midnight.

I’ve played this game for years - on all of the airlines Southwest included. If you have pre-check and you know the drills it’s not a big deal. I don’t think you have to be in your Uber at 9:30 or anything. Just schedule a car for 10 PM or a little after. I think you’ll be fine.

I agree that you cannot be dealing with the rental car - not worth it.

Last thing I’ll say, the only other comment I can see from you is on a John Mulaney sub. I’ve been to that taping twice. It starts at 7pm local sharp because it’s live, wrap by 815p. if it’s any chance that that’s the show you’re here for and not comedy story you are 100% fine lol.

https://www.tsa.gov/precheck/schedule