A $2,100 Trip to San Francisco and Portland for 30 Cents Out-of-Pocket!

This month’s marked with lots of travel. I just got back from a week in Japan. And tomorrow, I’m off to San Francisco and Portland!

I was tallying up my points totals and comparing what the retail costs would’ve been. This trip would’ve cost over $2,000 had I paid cash.

san francisco with points

I got 30 cents… will this be enough for 5 days in San Fran and Portland? :p

I should disclose ended up paying a little cash, in addition to my points. 30 whole cents. 😹

Here’s how I did it!

5 days on the West Coast for under a buck

Alaska’s had some amazing fares from Dallas to San Francisco and Portland recently – around $200 round-trip.

I’ve been wanting to visit Portland forever by now. And it’s been years since I’ve been to San Fran. I think I was 19 the last time I was there?

a sunset over a body of water

West coast is the best coast for amazing sunsets

So I cobbled together a multi-city itinerary that looked like this:

a screenshot of a screen


The final cost?

a screenshot of a computer


I planned this trip in January, and the $300 annual travel credit from my Chase Sapphire Reserve card had just reset. This credit, along with hotel points for the hotel stay, made my net cost exactly 30 cents.

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Gosh I love seeing this

In my recent post about the break even point of the Chase Sapphire cards, I did NOT include the travel credit. So depending on how you conceptualize this credit, I either paid $450 for the card, and got $300 toward a trip. Or, this credit reduced the annual fee to $150 because it’s a trip I wanted to take anyway.

Peeps think of their points, credits, and annual fees in various ways. Because I paid the annual fee back in September 2017, by the time January 2018 rolled around and the credit reset, it sure felt like I got those $300 flights for 30 cents.

Plus, I used Hyatt points transferred from Chase Ultimate Rewards points to cover 3 nights of hotels. I love this card!

3 nights in SFO

I snagged 3 award nights at the Hyatt Centric Fisherman’s Wharf. This is a Category 4 hotel (meaning you can use your Chase Hyatt Visa free night here), and award nights cost 15,000 points.

The nights we wanted were $274 plus taxes, which came to ~$957 total.

a screenshot of a hotel room

Price at the time of booking

Instead, I used 45,000 Hyatt points. I already had some in my account. And transferred what I needed from Chase Ultimate Rewards.

In this case, each point was worth a bit over 2 cents each ($958 / 45,000) – which is what I always strive to get from these points.

2 nights in Portland

OK. Why are hotels in Portland so expensive? All the cash rates were insanely high. Early on, I knew I’d be burning some points.

And with that thought, wanted to get the best combination of price and location. I settled on the Marriott Portland Downtown Waterfront. It has decent reviews on TripAdvisor and the location looks incredible.

The 2 nights I wanted were ~$857.

a screenshot of a hotel room


Most of the Marriott hotels in Portland were 35,000 points per night (so was this one). And the only Starwood hotel in town (The Nines), wasn’t available. I didn’t want to use Hilton points (too expensive), and I’d just burned most of my IHG points to stay in Japan.

So, I dipped into my Starwood balance and transferred 21,000 points to Marriott to top up my account for the 70,000 Marriott points I’d need.

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Lil transferoo

The 21,000 Starwood points became 63,000 Marriott points. And with that, I had enough to book the 2-night stay.

But I think of Marriott points as Starwood points (for now), because they’re still so valuable. So those 70,000 Marriott points were worth 23,000 Starwood points.

Which meant each point was worth nearly 4 cents each ($857 / 23,000) – a very good value. After this, I’m not using any more of my Starwood points until after the program changes in August 2018. But back in January, I was comfortable making the transfer and getting that value.

(Until August, I’m going to accumulate as many Starwood points as possible!)

By the numbers

Adding it up by retail value:

  • Flights were $300
  • 3 nights in SFO were $957
  • 2 nights in PDX were $857

The total cash price would’ve been $2,114. But I paid:

  • 30 cents for the flights
  • 45,000 Hyatt points for 3 nights in SFO
  • 70,000 Marriott points (23,000 Starwood points) for 2 nights in PDX

Hotel points got me 5 free nights in hotels. And because the Chase Sapphire Reserve’s $300 annual travel credit kicked it, I paid 30 cents for the flights.

And now, I leave tomorrow – I’m so excited to go back to the West Coast!

Bottom line

This weekend, I’ll enjoy 3 nights in San Francisco at the Hyatt Centric Fisherman’s Wharf and 2 nights at the Marriott Portland Downtown Waterfront. I’m flying there on Virgin America and back on Alaska. It’ll be interesting to compare them after the big merger.

My total out-of-pocket cost was 30 cents, for a trip that retails over $2,100. Stuff like this is why I love points & miles (and my Chase Sapphire Reserve card) so much.

Even cooler: I have $15 in Uber credits from my Amex Platinum Card, so I’ll only have to pay ~$10 to get to the airport. Plus I’m going with 2 friends and will take them to the Centurion Lounge @ DFW when we get back (we’re flying out of Love Field)!

The only thing I’ll really pay for is food and attractions this weekend, which is awesome. I’m also getting a new tattoo in Portland (!!!), so I’ll pay cash for that.

So now one last thing: anything cool I should check out in SFO or PDX? Cool breweries, fun local bars, great restaurants, or anything else unique to either city?

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About Harlan

Just a dude living in Memphis, traveling, and working toward financial independence.

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  1. In Portland. Blue Star donuts. Andina which is a very nice Peruvian tapas place or if you wanna hit the opposite end of the spectrum there’s food carts everywhere in downtown and it’s very walkable (no hills like SF). Get a day pass for the trolly that runs through downtown. It’s like $5 and you can go all over the central parts of DT. There’s breweries everywhere so just pick and drink away lol. For nightlife check 2nd and 3rd street area near Chinatown, especially on the weekend. Idk if you’ve been to Portland before but our DT is small compared to other major cities and easily walkable. Your also lucky in that it’s gonna be in the 70s when you get here, something we’ve been waiting for all year. Bring some good shoes to walk in. And if you have half a day rent a car and head to the Columbia River Gorge while the weathers nice and check out Multnomah Falls. You don’t even have to bring hiking shoes, there quite a few short (less than 2 mi) paved trails that lead to view points and waterfalls all along the freeway before and after Multonomah Falls which if I remember is exit 32 on I-84. It’s only about a 30-40 min drive out of downtown and just seeing the gorge even if you don’t want to do any hiking besides stepping out to get some fresh air is tremendously worth it. Honestly, quintessential Oregon is gettin out in nature anyway. Have a good time, I’ll be following along. I’m an Uber driver part time btw so I got more suggestions if you need em lol.

    • These are all excellent tips – I’ve copied them into my Evernote file for the trip! Thank you so much! I will have to do an update. I already get the feeling it’s going to fly by and feel so short – I will try to pack in as much as possible. And yay for the nice weather – Portland knew I was on the way! 😉

      Thanks again, I really appreciate the time you took to send this.

  2. Harlan,

    William has some great tips. Hit me up and I can give you some more ideas or meet up for a beer. There’s so much to do downtown and the Marriott is a good location. We are finally in for some sunny weather so you hit a great time.

    BTW, great job maximizing your travel credit!


    • That’s awesome, I would love to have a brew with you! And yup, when I saw it was exactly $300 and change, it was just too perfect. Can’t wait to get there!

  3. Check out the booming brewery scene in SF’s Dogpatch — Harmonic, Voodoo, Smokestack (Magnolia), Speakeasy, Laughing Monk, Seven Stills (ok the last few are more Bayview, but still…). Have fun!

  4. Marriott has some pretty cool properties in Portland, but since you’ve already booked ¯\_(ツ)_/¯

    I go to San Francisco very often (very) but it’s for work and generally stay in the same area. I love the Powerhouse (bar)…it’s a grungy little neighborhood gay bar in Soma. Hog & Rocks for oysters and charcuterie. The St. Regis has a bonkers tequila bloody mary in the lobby. Zuni Cafe for the roast chicken, but you need to give them 45 minutes and it’s a plate as big as your face. YANK SING FOR DIM SUM (people will give me shit for that b/c it’s wypipo dim sum but it’s SOOOOOOOOOO GOOOOOOOOOD). The Yank Sing on Stevenson is the one to go to…it’s in the cut–some little alley, but yeah… pls.

    They’re putting in a St. Regis in Portland next to all the food trucks–that’s gonna be fun 🙂 ENJOY!

    • I can still cancel/rebook if there’s room at another one – open to ideas!

      And thank you for all the tips – copied them into the note I’ll use for the trip. Appreciate it so much!

      • The Hi-Lo is where I recently stayed for a work trip (the Nines was too expensive). Our paid rate was about $200 before tax–it looks like for your dates it’s $257. I really liked the location. There was a fun gay bar across the open parking lot in front of the hotel…can’t remember what it was called but there’s a flag 😛 Also, remember there’s no sales tax in Oregon! I had just bought a Macbook Pro, but then the client mentioned something about not having sales tax, so I went and bought another one and returned the one I bought in Los Angeles. 🙂

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