Travel Hack Completed …..Somewhat

As folks know, Mrs. 39 Months and I took the opportunity to travel to Northern California and Oregon recently, both to enjoy the scenery and for her to take a class in shoe making. It was a great time, and one of those opportunities everyone should take advantage of if they get the opportunity.

I also wanted to use this trip to put into practice some of my travel hacking skills. As you may remember, I’d worked hard on the two Southwest Airlines cards in order to get to 110,000 miles and get the companion pass. I have now been working on the Chase Sapphire card, to try and nail down the 60,000 bonus points for that.

Overall, the trip consisted of 10 days (2 days in the air, 8 days on the ground). We flew into San Francisco, saw a few sights (Cathedral, Fisherman’s wharf, etc.) and then hit the sack. The next day, we visited Alcatraz, and then headed north. The following three days were spent in Northern California and Oregon, visiting national parks and enjoying the outdoors. We ended up Wednesday in Portland, where Mrs. 39 Months spent the next 4 days in class, while I traveled about and saw the city and surrounding area (Columbia River, City of Portland, etc.). We finally headed home on Monday (long flight).

So how did my hacking do?

  • Air flight: free (except for some fees) – savings of $1,088
  • Rental car: paid $338 for 10 days through Alamo, plus gas (about $120). Didn’t use any points, but all the cost got onto my Chase card, helping me towards my goal for the free 60,000 points.
  • Hotel: Due to where we were staying in the national parks, I couldn’t really use any points on stuff, but we did get the hotel in Portland for free: savings of $745
  • Food, Gas, other: Couldn’t use points on these, but again, was able to use the charges on my Chase card to hit my goal. By the end of the trip, I had achieved the usage on the card to get my 60,000 free points!

Overall, trip for two, Philadelphia to San Fran, travel to Portland, and then back cost around $1,512. I’m sure many of the really experienced travel hackers could have saved even more, but I’m pretty happy.

Some lessons learned:

  1. Southwest companion pass is awesome. Wife traveled across the country and back for free!
  2. It pays to get points from various vendors, not just the ones with Chase. I had several hotel options in Northern CA/Oregon that I could have used points for (ex. Holiday Inn express) that I didn’t have points for, so I had to pay cash for.
  3. Haven’t figured out a way to pay for car rental with points yet. Maybe used my 2% cash-back Citi card to pay for it.
  4. Food/Dining out is difficult to use points for – better to use card to pay for it with case and collect the points.

We had a great time, and I learned a lot about travel hacking. Time to plan the next big trip (probably 2019). Maybe the Grand Canyon?


Mr. 39 Months

2 thoughts on “Travel Hack Completed …..Somewhat”

    1. Good idea.

      I think one of the other errors I made was not using the card travel portals to book the trip.

      Thanks for the tip!

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