Pam
One of the biggest myths I hear is, “I wish I had known I needed to book a trip to Europe [or anywhere] sooner because now it’s too late to book my trip.” Actually, that’s often not true. Time and time again, I have great luck finding last-minute flights with points and miles. Particularly when my plans were rapidly changed (a safari canceled the day I was to go to Kenya and flooding in Auckland, New Zealand when I was supposed to leave the next day). These two instances made me a believer in last-minute award bookings.
While cash prices often skyrocket as your departure date gets closer, award prices don’t always follow the same pattern. In many cases, airlines actually release more award space in the days and weeks leading up to departure. It’s one of those things that surprises people until they experience it for themselves.
Airlines don’t usually want premium seats crossing the Atlantic or Pacific empty. If those seats haven’t sold, many airlines would rather make them available to travelers using miles than leave them unoccupied. Add in travelers changing plans or canceling award tickets, and suddenly you have opportunities that simply weren’t there earlier.
Some of our best business-class flights have been booked just days before departure. We’ve scouted flights to Europe that seemed impossible to book six months out, only to see award space open up the week before the trip.
That’s one of the reasons I love having a healthy balance of transferable points. They’re like an emergency travel fund that’s ready whenever an opportunity shows up.
Instead of having all of your points tied up with one airline, having points in different programs like Chase Ultimate Rewards®, American Express Membership Rewards®, Capital One Miles, Citi ThankYou® Points, and Bilt Rewards give you options. When award space becomes available, you simply transfer your points to the airline with availability.
Now, does that mean you should always wait until the last minute? Definitely not.
If you’re traveling during Christmas, spring break, or another peak travel period with fixed dates, booking early is still your best strategy. Families who need four or five seats on the same flight will usually have better luck planning well in advance.
But life doesn’t always give us months to prepare:
Those are the moments when a stockpile of points and miles really shines.

Even if you don’t find nonstop flights from your home airport, being willing to make one small adjustment can completely change what’s available. Maybe you fly out on Tuesday instead of Wednesday. Maybe you connect through another hub. Maybe you fly into Paris and home from Amsterdam instead of making it a round-trip. Those little changes often open up award space that wasn’t there before.
Another thing I remind people of is this: don’t search once and give up. Award availability changes constantly. People cancel trips, airlines add flights, and additional seats are released. Someone who looked yesterday may see something completely different today.
I’ve had plenty of trips where I searched every morning for a few days before suddenly finding exactly what I wanted. That’s one of the reasons I always tell people to stay persistent. Award travel rewards the people who keep checking.
One of the biggest advantages we have today is the number of tools that make those searches easier. Instead of checking airline websites one by one, services like PointsYeah, Roame, Seats.aero, and Thrifty Traveler Premium can help you spot award space much faster.
So if you’ve been looking at expensive cash fares and thinking your trip is out of reach, don’t stop there. Open up an award search. Check a few airline partners. Be willing to shift your dates by a day or two. Look at nearby airports.
In fact, if you’ve already booked an award flight, it’s often worth checking back every so often. You may find the exact same flight available for fewer miles, or you might discover a better itinerary that wasn’t there when you originally booked. Many airline programs let you cancel or change award tickets for little or no fee, so rebooking can be an easy way to stretch your points even further.
I was traveling back from London to Boston on a Virgin Atlantic flight for 48K points + 600 GBP. I decided to look and see what I could find if I hadn’t booked this ticket months ago. Here’s our original ticket:


I ended up changing to this flight as it got me all the way home, I didn’t have to book a separate flight Boston-Denver, and I saved about $400 in taxes and fees for each of us. It was 22K points more per ticket, but we got to travel first class from Miami home, and it worked out better for us.
It goes to show that flights—even business-class flights—can be found last-minute and can sometimes be even better than what you originally booked!
While I still prefer to book a flight as soon as I plan to take it, there is a strong case for last-minute award bookings as well. Time and time again, I have found great deals, even at the last minute!
Last-Minute Business Award Flight to London
Podcast 176. Pivoting When Your Trip Gets Canceled

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