This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. For an explanation of our Advertising Policy, visit this page.

TPG reader Diana sent me a message on Facebook to ask about booking award flights:

“I’m trying to book three award tickets from New York to San Diego. The mileage cost has gone up since I first started checking. Will it ever go back down?”

Anyone who travels regularly has probably kicked themselves at some point for waiting to buy a flight until after the price went up. In that situation, you might wonder whether you should wait a bit longer and see if lower fares return, or book right away before they get any higher. The general trend for both paid fares and award tickets is that prices go up closer to the departure date. However, there are exceptions, and sometimes your patience will be rewarded.

Award availability doesn’t change in a linear fashion. Many airlines open award space in chunks, so you might find zero saver level availability one day, and then find half a dozen seats available the next day. Space can also open up when other passengers modify or cancel reservations, so it pays to keep looking. If you don’t have time to search for flights every day, ExpertFlyer can search on your behalf and notify you when award space becomes available. The service isn’t free, but it’s easier than repeating the process manually.

Whether or not you should wait depends on how much risk you’re willing to accept. If you’re only a few weeks out from your trip and need to cement your plans, you might be better off just taking what’s available. If you’re booking further out or if your itinerary is flexible, then you can wait and see if prices go down (even right up until the last minute).

There are also a few strategies to avoid this dilemma entirely. Award change and redeposit fees are often waived if you have high-level airline elite status, so you can just book at the current rate and then re-book later if the price goes down. The same goes for Southwest Airlines awards even if you don’t have A-list status, since Southwest doesn’t have change fees. If you book your flights and then the price drops the following day, you may also be able to take advantage of the 24-hour airline hold and cancellation policies mandated by the Department of Transportation.

Not all
You can always rebook Southwest flights with no penalty, so there’s no need to wait for lower prices.

Another factor to consider is that airlines sometimes charge more per person when you try to book several tickets at once. If one of your tickets is the last available in a given fare bucket, then you could end up paying a higher price for all of them, including the first one. It’s worth checking to see how the fare changes when you attempt to buy fewer tickets. Splitting your group across multiple reservations could be a problem if you end up having to change or cancel your flights, but the savings probably justify the risk.

If you have any other questions, please tweet me @thepointsguy, message me on Facebook or send me an email at

Chase Sapphire Preferred® Card

With great transfer partners like United and Hyatt, 2x points on travel & dining and a 50,000 point sign up bonus, the Chase Sapphire Preferred is a great card for those looking to get into the points and miles game.

Apply Now
More Things to Know
  • Earn 50,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $625 toward travel when you redeem through Chase Ultimate Rewards®
  • Named Best Credit Card for Flexible Travel Redemption - Kiplinger's Personal Finance, July 2016
  • 2X points on travel and dining at restaurants worldwide & 1 point per dollar spent on all other purchases.
  • Earn 5,000 bonus points after you add the first authorized user and make a purchase in the first 3 months from account opening
  • No foreign transaction fees
  • 1:1 point transfer to leading airline and hotel loyalty programs
  • Get 25% more value when you redeem for airfare, hotels, car rentals and cruises through Chase Ultimate Rewards. For example, 50,000 points are worth $625 toward travel
  • No blackout dates or travel restrictions - as long as there's a seat on the flight, you can book it through Chase Ultimate Rewards
Intro APR on Purchases
Regular APR
16.49% - 23.49% Variable
Annual Fee
Introductory Annual Fee of $0 the first year, then $95
Balance Transfer Fee
Recommended Credit
Excellent Credit

Editorial Disclaimer: Opinions expressed here are author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.