Travel Hacking

  • Of course, the easiest travel hack is to get a travel credit card. We use the Chase Sapphire Reserve, and easily earn back the annual fee. We also have the Chase Freedom, which has rotating 5% categories, and then we can transfer over these points to the Reserve account for a higher redemption.
  • The Southwest Companion Pass. We are not particularly loyal to any specific airline, though we do fly Southwest quite a bit, especially after I was able to score a Companion Pass through credit card sign up bonuses. Southwest will give you the Companion Pass for the remainder of the year you earn it, plus the entire following year, so by being very meticulous with my sign-up dates and spending, I earned this in early January 2018 and was able to use it for all of 2018 and 2019! The points requirement is now 120,000, but still doable through smart sign-ups and/or spending.
  • We follow free sites, like Scott’s Cheap Flights, The Points Guy, and Secret Flying, for cheap flights. We scored our cheap flights to Costa Rica over Thanksgiving through a deal sent out on Scott’s Cheap Flights.
  • Hotels–business travelers are often staying in the same brand of hotel on their trips, so they are more likely to stay brand loyal. We are not those people, so I often look for a better deal/better room/better location, etc. I like to use, and you effectively earn 10% back by just signing up for the free rewards program, as after paying for 10 nights, you get 1 night free that is the average of the 10 nights paid.
  • Shopping portals! I do most of my shopping online (sometimes shop online, pick up in store for local places) and consider it a fail if I can’t at least double up on points when buying something. I use to find the sites with the best current points value, and also check Upromise to see what their current offer is as they are not listed on cash back monitor. Lastly, I check my frequent airlines such as Southwest to see if they are offering bonus points with a minimum spend, as they often do near holidays or back to school times.

Extra Credit

  • United Mileage Plus app–This is how you can triple dip on points! I have accumulated quite a few United miles simply by using this app. You buy e-gift cards through the app, which can then be used through the online shopping portal. So, you earn points/miles by using your card for the purchase, points/miles for United by buying on the app, and then points/miles by shopping through the shopping portal with that gift card. They also have a few apps that you can click through to, such as the app. Currently, they are offering 2 United miles/$ spent on the app if using the rewards, as long as you click through to the app from the Mileage Plus app.
  • For an even crazier earning, use, which is an extension of Swagbucks. On here, you can buy a gift card. I would use my Citi Double Cash card. So 2% back on the purchase + 5% back in Swagbucks points, up to 7% back so far. Then, you could use whichever portal you prefer to book the room on For example, on Upromise, you can book on for 2% if claiming rewards. So now we are up to 2% +5% + 2%, for a total of 9% back. Combine that with the 10% back on rewards bookings, and you are now up to 19% back on the cost of your hotel room!
  • When grocery stores are in the rotating 5% back category for the Chase Freedom card, I stock up on gift cards like that I can use in the above scenario, instead of purchasing through the site. I then fill up both cars at the same time at King Soopers fuel stations to maximize my fuel rewards on the gift card purchases as well. It’s even more lucrative when King Soopers is offering 4x fuel points on gift cards when the Freedom card is offering 5x points at grocery stores!
  • The Chase travel booking portal. Of course there are times when transferring your Chase points directly to the airlines is more beneficial, but I also always check the redemption on the Chase portal. When you book through the portal, it appears as a cash booking, so you still get to claim the miles. I recently found Southwest flights for an upcoming trip that were not only less points on the portal, but then gave us over 1,000 SW miles/person for taking the flight! That we paid for with Chase points! Score!
  • Cash back apps. I have used both Pei and Dosh for extra cash back. You link the cards that you use to these apps, and that’s it. They automatically give you cash back when you use your card at affiliated places. Admittedly, I have not earned a ton back from either site yet, but $30 for doing nothing other than installing the apps and using my cards is worth it. They also sometimes have extra cash back, such as an offer on Dosh currently for $30 back on your first hotel booking. Click here for my referral link to Dosh, or here for my referral link to Pei, which will give us each $2.50 just for you signing up!

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