Generally we book our flights before we book our lodgings. However, this can be tricky. For example, we had decided to visit Boston this year for the Marathon. Unfortunately for us it's also Easter Weekend and when I called our B and B accommodations contact there, I found out that everything in the downtown core has been booked for months (and we're not prepared to pay $200+ per night so a downtown hotel was out of the question). So, we're not going because we aren't prepared to stay outside of downtown.

I try to check out accommodations, ask if the room reservation can be held for 24-48 hours before we confirm, and then book a flight. Usually it works out fine.

Lucy, Toronto