Skyscanner users can make their destination “everywhere,” which brings up the cheapest flights across the world from a given airport.
Expedia will track ticket prices and tell you when to book based on historical data if you join its free One Key rewards program. After you’ve booked, new A.I.-based apps will monitor the fare and, if it drops, request a refund from the airline, usually for a fee.
Keep in mind that Labor Day weekend airfares are highest if you leave on Friday, Sept. 4, and return on Monday. A recent check on Kayak for nonstop round-trip fares between New York and Portland, Maine, over those dates started at around $500. If you returned on Tuesday, Sept. 8, you’d save $50. And if you shifted the trip forward to fly on less busy days — out Wednesday, returning Saturday — round trips started at around $240.
Spend Miles
Don’t wait to use loyalty points. What 50,000 miles bought yesterday might require 80,000 tomorrow.
Airlines have made it easier to spend points, even at the last minute.
“In the old days, airlines restricted award seats, and it could be tough to find a flight with miles late in the game when demand was high and many seats were already booked,” said Julian Kheel, the founder and chief executive of Points Path, a service that compares prices in cash and miles and tells you which is the better deal. “However,” he said, “today, most airlines have seats available with points and miles so long as they’re available with cash.”