Originally Posted by
cedric
The next flight *is* the 11pm.
The risk here is that if OP books the 8pm and the 11pm is full, they will have to wait until the 12:30am.
I know, that 1230 am flight is probably ~15-20% of all the segments I've flown in the past five years.
If OP wants to book the tightest connection possible, then yeah, waiting several hours for a standby seat is what's involved in losing that bet.