2020 was a year that left me feeling bitter about travel. Plans were cancelled. Guilt was laid on thick. Addressing these types of topics was nerve wrecking and exhausting and keeping our travels to myself seemed to be the way to keep from spoiling them.
I think I will still plan on documenting the trips we have taken since I last posted. I published East Coast Train Trip from Phoenix, AZ in Dec 2019 and never made it back around to write about that experience. We also had a hard trip experience in January 2020 when we got what we now realize was probably Covid, cancelled the long awaited Costa Rica trip, and had a really rough drive home from Florida. Lockdowns then prompted cancelling our Preakness trip (damn was I stoked about that 3.7 cent per point Hyatt redemption!), a weekend in Chicago and killed our dreams of visiting Hawaii. BUT our companion pass was extended for an additional YEAR and we logged 10 National Parks in 10 months. I have so many pent up places and stories to share. Oh, and we also decided to change our home base in April this year from Metro Detroit to Upstate South Carolina!
I guess I’ll start with a review like I did for 2019 and I’ll try and work my way forwards on our trips each week! If you’re not into the charts and numbers, check the Trips tab for new stories.
Companion Pass
2020 was supposed to wrap up our 22 months of Southwest Companion Pass, but since flying was a no go for a chunk of the year they extended it to June 2021 and then again until December 31, 2021. We still managed 2.5 round trip flights in 2020. We took less than half the flights and used 1/3 of the points spent in 2019. We earned an additional 27,685 points from annual rewards bonuses, credit card spending and shopping portals. That’s more than we spent!
More than ever, having the flexibility to cancel and change flights was a life saver. I was able to get our points and money back for cancelling our flights to Costa Rica, Baltimore and push back our flights to Denver until travel restrictions were lifted. I did find that because of feeling down about all the changes and cancellations, I never got too attached to our trips and my planning process didn’t happen the same. As a result I have fewer metrics documented on cash costs for flights or how much prices changed over time.
I did make the decision to cancel my SW Business card at the end of 2020 because I knew my time with the companion pass was coming to an end and I still had more points than I could spend. I considered cancelling the personal card as well, but they offered me a deal to keep it where the perks outweighed the discounted annual fee. I did move all spending off that card to my new Freedom Unlimited so I will have near 0 points from CC spend in 2021.
- $149 annual fee
- $75 Travel Credit
- 4 Free Upgraded Boardings ($80)
- September 19 $40
- October 3 $40
- Anniversary Bonuses ($202)
- Priority Card 7,500 points
- Premier Business Card 6,000 points
- $149-75-80-202 = Earned $208 worth of points and perks
Points Spent: 27,455
Cash Spent: $56.00
Saved: $768
Chase Sapphire Reserve
This card got a sweet upgrade in 2020 since having a boojie travel card wasn’t incredibly relevant. In addition to some temporary earnings categories (groceries, streaming) Chase introduced the Pay Yourself Back feature.
How it normally works: You earn points based on category (3X points on Travel & Dining, etc). Once you have those points you can use them in the Chase portal at 1.5X to book travel or transfer to travel partners like Hyatt for 1X.
- Example: I want to book a hotel room in the Chase travel portal. The cash cost is $89.01. Instead of redeeming at 1X ($.01 per point) and using 8,901 points, you get some extra “juice” in your points and redeem them at 1.5X ($.015 per point). Total points cost is instead 5,934
How it works with Pay Yourself Back: You earn points based on category (3X points on Travel & Dining, etc). Once you have those points you can use them to erase purchases in particular categories from your card at 1.5X. This is essentially cashing them out at the same $.015 per point you would get redeeming the points for travel in the portal, but with the flexibility to cancel out purchases you made, or justify travel purchases bought outside the portal.
- Example 1: I want to book a $100 per night Airbnb, but I can’t use my points for that. However, since I do all my spending on this card I have $100 worth of dining purchase I can “erase”/cash out my points towards.
- OR Example 2: For whatever reason I’m not traveling right now. Rather than let my points sit, I’d love some cash back to lower my expenses for the month on dining out, groceries or a home improvement project (all of those are categories eligible for Pay Yourself Back)
I was free of the portal and justified in booking via Airbnb, 3rd party sites and direct with the business owners who needed it! Plus then I’d earn 3X points on that money again (because all travel spend earns 3 points per dollar) and am eligible to use tools like Rakuten to earn even more cash back. We cashed out over $1,000 in points in 2020.
In 2020 the increased annual fee was supposed to start, but in light of the pandemic they gave a credit to eliminate the increate for those that had already been charged. After adjusting for the $300 travel credit, the annual fee was again $150. We had a few new benefits, but getting value in year 2 without as much travel was a bit of a struggle. Also, finding this data nearly a year later is a struggle as well.
| Program | Savings |
| Door Dash Credit | $ 60 |
| Lyft Pink | $ 8 |
| 1.5X Bonus Transferred Pts | $ 125 |
| $ 193 |
Remember all those great hotel redemption I had for 2020? Yeah all those were cancelled. And luckily we lost $0!
We felt more comfortable going back to Airbnb stays in the pandemic era, but thanks to Pay Yourself Back I could still count those as a points win. We also experienced our first Hyatt on the way back from Florida and despite their fresh breakfast not being available most of the year, we became loyal to their brand because of the consistency & value of transferring our points from Chase.
| Location | Length | Points | Cash Value |
| Homestead | 1 Night | 4,902 | $ 73.53 |
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| Holiday Inn Express Ocala | 1 Night | 7,232 | $ 108.48 |
| SureStay Macon | 1 Night | 4,856 | $ 72.85 |
| Hyatt Bowling Green | 1 Night | 5,000 | $ 106.16 |
| Hyatt Moab | 2 Nights | 16,000 | $ 500+ |
| Red Sands Hotel | 1 Night | 4,726 | $ 70.90 |
| Hyatt Salt Lake | 1 Night | 5,000 | $ 224 |
| Hyatt St. Louis | 1 Night | 5,000 | $ 160 |
| 52,716 | $ 1,316 |
Other Cards
We also opened 1 new card.
- I decided I wanted to ditch the Southwest Premier as my daily spender. I did a deep dive into the categories we spend most on and most spend I was doing fell outside traditional categories. I decided the Chase Freedom Unlimited would be perfect because it would give 1.5% on all purchases with no annual fee. It’s also another card I can transfer points to Adam’s Reserve and get the 1.5X Chase Sapphire Reserve boost.
- My Amtrak card was cancelled at the 1 year mark to avoid paying the annual fee again.
Grand Totals
Annual Fees: $697
Value redeemed: $3,084
