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TPG reader Elliot sent me an email to ask about planning award travel:

“I have rewards from Amex, Chase, SPG and American Airlines; now I’m planning a honeymoon with my wife (maybe to Southeast Asia or South Africa), but I have no clue where to start! What’s your advice?”

There seem to be two prevailing approaches to award travel. Some people simply decide where they want to go, and then set out to earn the rewards they need to get there. Others take a more opportunistic angle by collecting points and miles when they’re easy to get, and then redeeming them when the moment is right (like during an award sale). Both approaches work, and you don’t have to be fully devoted to one or the other.

That said, I get a lot of questions from readers like Elliot who have stockpiled rewards haphazardly and are unsure what to do with them. Don’t feel bad if you fit that description; loyalty programs aren’t always intuitive, and sometimes it’s unclear which one you should use to maximize your travel. However, points and miles make a bad long-term investment, so it’s best to have some kind of plan for them. That’s why I think the first approach is easier for people who are new to the game.

The first step is to decide where you’re going. Check out destinations that interest you and see which hotel brands have a presence there, keeping in mind the rewards you have available. There are plenty of great properties to choose from both at the high end and in the lower tiers. If you don’t have enough points to stick with one hotel for your entire trip, you could divide your time and explore more than one area, or mix in some points + cash bookings to stretch your rewards further.

After you’ve narrowed your search to a few good hotel options, start looking at flights. Use Google Flights to see which airlines and alliances serve each destination, and then start checking award availability. Once you’ve put together an itinerary that works for you and has award space, book the hotels first, since those reservations are easier to change or cancel.

IMG Starwood SPG Phuket Naka Island banner
Book your hotel first, because the reservation is more flexible. Image courtesy of The Naka Island Resort & Spa.

Planning award travel is generally easier when your schedule is flexible and you book far in advance. Setting travel goals with a realistic timeline will help ensure you have the points and miles you need, and that they don’t go to waste. On the other hand, there are still opportunities when booking at the last minute, so don’t give up hope if you’re short on time.

For more tips on the process of booking awards, check out these posts:

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

Chase Sapphire Preferred® Card

Even after the introduction of the Chase Sapphire Reserve, the Chase Sapphire Preferred is still a fantastic choice if you want to avoid the Reserve’s $450 annual fee, earn 2x on all travel & dining and earn a 50,000 point sign up bonus.

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.