A listener recently wrote into the podcast with a question that hits at the core of my travel philosophy. He said:
“You talk a lot about reshopping travel deals, but how do you do it safely? Do you book the new deal before canceling the old one, or cancel first and then rebook? What happens if you cancel and the new deal falls through? And how do airlines handle this compared to cars and hotels?”
These are the right questions. Reshopping your travel reservations is one of the easiest ways to pocket extra cash on a trip you were going to take anyway, but if you do it in the wrong order, you risk getting stranded or left with nothing.
Here is my golden rule of travel reshopping, along with exactly how I handle rental cars, hotels, and airline tickets.
The Golden Rule: Lock It In First, Cancel Second
The golden rule of reshopping travel is simple: Always confirm your new, cheaper reservation before you cancel your original one.
Never, ever cancel what you have sitting in hand on the hope that a lower price will go through. Travel prices and availability fluctuate by the second. If you cancel your original booking first and then the lower rate suddenly disappears or fails to confirm, you could end up with a higher price — or no reservation at all.
I’ll give you a real-world example from a trip I just took to California. While I was sitting on the plane, I took advantage of the flight’s free Wi-Fi and thought, “You know what? I rebooked my rental car last week, but let me check if it’s gotten any cheaper again.”
Sure enough, the price had dropped. I booked the new rental car right there at 30,000 feet, waited for the confirmation screen, and then went back and canceled my original booking. That quick check saved me $45.
How To Reshop Rental Cars
Rental cars are the easiest and safest travel category to reshop.
Most traditional rental car reservations don’t require upfront payment and have no cancellation fees.
Reserve your car as early as you can without prepaying. In the days and weeks leading up to your trip — even right up until the day you fly — check rates again using a comparison site or a free tracking tool like AutoSlash.
If you spot a lower rate, complete the new booking first. Once you have the new confirmation number in hand, cancel the old one.
How To Reshop Hotels
Hotels are another great opportunity for savings, provided you book the right kind of rate.
Never book non-refundable hotel rooms. I always choose rates that offer flexible cancellation without penalty — usually allowing you to cancel up to two or three days before arrival.
During the week of the trip, reshop my hotel bookings. Because of cancellation policies, you usually can’t do this at the very last second like a rental car, but if you find a lower rate a few days out, book the cheaper room first. Once that new confirmation hits your inbox, cancel the original reservation.
The Catch: Reshopping Airline Tickets
Reshopping flights is a whole different ballgame and carries much more risk.
Airlines will generally not allow you to double-book yourself on the exact same flight under the same name. Their automated systems will often flag and cancel duplicate itineraries. Moreover, when you cancel a flight, you rarely get cash back — you get an airline credit.
For example, on that same recent trip, I was originally booked on Delta. Right before the trip, I found a last-minute deal on American Airlines. I booked the American flight first, and once it was locked in, I canceled my Delta ticket.
Because of the cancellation, I received a $352 Delta credit with 10 months left to use it (since airline credits are typically valid for one year from the original date of purchase).
Should You Reshop Flights?
If you fly frequently: Reshopping can make a lot of sense. I fly constantly, so that $352 credit is as good as cash in my pocket — I know without a doubt I’ll use it before it expires.
If you fly once or twice a year: Be very careful. Unless you are positive you will take another trip with that specific airline within 12 months of your original booking date, that flight credit could expire unused. In that case, “saving” money by switching flights actually costs you cash out of pocket.
Summary Checklist for Reshopping
Book flexible options upfront: Choose pay-at-counter rental cars and refundable hotel rates.
Shop again close to your travel date: Check prices a week out, a few days out, and right before you depart.
Secure the new rate first: Complete the new reservation and wait for the confirmation.
Cancel the original booking: Immediately cancel the old reservation to avoid double charges or no-show fees.
Mind the flight credits: Only reshop flights if you are certain you’ll use the resulting airline credit before it expires.
The post The Safe Way to Reshop Your Travel Deals and Save Hundreds appeared first on Clark Howard.