Trying to put Patches in Barcelona

I went over to Patches' place tonight with Joe Brooks. We played Seafarers of Catan and it was mucho denero fun.
When we were getting ready to leave Patches mentioned that we needed to celebrate November 5th. That would be the day he returned from Europe if he'd actually gotten into Europe. Since England deported him he needed to get directly to Barcelona, as that's where his return flight is from.
Joe Brooks and I got the stupid awesome idea that Patches could still get to Barcelona before the return flight. Our plan is that he flies out on November 2nd and gets at least 36 hours to party in Barcelona before the return flight.
We found a ticket from Toronto to Barcelona for $675 leaving November 2nd at 6:30 PM. As this is a 13 hour drive with a 1 hour time zone change he's going to need to leave at about 2 AM to get to Toronto on time. Unfortunately, his return flight is to Chicago. These leaves a problem for driving to Toronto. Joe Brooks is looking into it. Hopefully we'll get it all figured out.