Getting the best price and how to start your award searches

Mar 01, 2025

Holiday sales seem much exciting than they used to be. I remember getting up at 3am in medical school to wait outside of department stores to score deeply discounted merchandise on Black Friday. But as Black Friday has proliferated into multiple days throughout the year, studies show that the overwhelming amount of Black Friday "deals" have been lower priced at a different time of the year! What's a discerning consumer to do?

  • Use a website like CamelCamelCamel. It tracks prices throughout the year to show you if you are really getting a deal.
  • Don't buy anything without a shopping portal. A price might not be discounted, but earning through shopping portals gives you a multiplier on your purchases. Rakuten, my favorite portal, earns Membership Rewards when you have an Amex Membership Reward-earning card. If you don't have Rakuten, sign up with my referral and we both get 3000 points.
  • Buy experiences rather than things. Let's be honest, there's enough stuff in the world to last us generations. Whether it's a vacation, meal, or other activity, consider that experiences bring longer-lasting happiness and memories than things. And what about the gift of learning? Consider my courses!

 

 

Tip: How to start your award bookings

Many folks know how to earn lots of points. But searching for award space can be very overwhelming. How do I start my award searches?

I always start with the free website FlightConnections.com. I input my destination to see all the carriers who service that region. That’s always my starting point for looking up awards.

 

Once I understand which airlines fly to my destination, I can look up their alliances and partners:

  •  Google "<airline> partners and alliance."
  •  You can also Google “sweet spot awards to <destination>” to see if there are any key rewards to focus on.

If I have specific dates I’m looking for and have multiple airline options to get there, I’ll use an award search tool:

  •  Pointsyeah.com
  •  Awardtool.com
  •  Point.me

 These sites search for multiple airline options across a few dates. Often it makes sense to search only for the long-haul portion, and piece together short segments separately.

Stay tuned for part 2 about how I begin my award searches!

Credit Cards: What I opened

I'm normally not interested in co-branded cards (cards that only earn one type of points - the points of the brand on the credit card), but sometimes it can represent a good earning opportunity.

Recently Alaskan and Hawaiian Airlines merged, representing a good opportunity to collect more Alaska miles, since the programs can now transfer points between each other. I considered buying some Hawaiian miles on sale but instead was presented with a welcome offer of 70,000 points. Why not!

After earning, I'll transfer these to Alaska to book other One World carriers or partners, like Air Tahiti Nui, Condor, or Starlux. Additionally, if you have a Hawaiian airlines credit card, you can transfer miles for free between accounts. If you and a family member both have Alaska miles, you can combine them. One person can transfer the Alaska miles to their Hawaiian account, then combine them into another person's Hawaiian account, and then transfer all the miles into a single Alaska account.