If he just wants to sleep with her(again presumable), this is overkill and he probably could have sealed the deal for a much lower cost. If he actually wants to get back in a relationship with her, then he's just dumb for spending all this money on tickets to Vegas because that probably won't get him anywhere.
Try Chicago to Milwaukee. I'm not convinced the plane left the runway.
In college I flew from Rochester to Minneapolis. I think the pilot just flew a couple hundred feet in the air and followed hwy 52.
For whatever reason flying out of Rochester and connecting in the twin cities to Denver was cheaper than starting in the twin cities.
I also got a return flight rerouted to Minneapolis once. Had a 4 hour layover to catch a flight to Des Moines. The cost of just renting a one way car was so expensive so that wasn't an option. It was very frustrating knowing I could have been home for an hour if I had driven while boarding a 1 hour flight in a tiny plane.
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