A weekend for two in Portland, Oregon for $235: How I made it work

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Trip length: 2 days

Total cost: $ 235

Vacation days used: 0

Portland Details

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What are holiday weekends for if not travel?

With a long weekend looming, my boyfriend and I researched destinations that might be doable for a couple of days. Since I was sitting on 12,000 unused IHG points, I checked out IHG’s PointBreaks list and ran down the list of hotel options. The PointBreaks hotels are bookable for only 5,000 points per night, so I had enough points for us to get two nights free at any hotel on the list. We quickly settled on Portland, as he hadn’t yet visited the Pacific Northwest and it seemed like one of the more interesting destinations on the PointBreaks list that would actually be doable for a weekend. I’d previously done Portland on an even shorter trip, but I was anxious to spend a little more time there and explore some different areas.

The Southwest Companion Pass was essential to making this trip work. By earning 110,000 points in a year, my boyfriend secured a Companion Pass for the remainder of this year and all of next. This allows him to fly another person with him for free, whether on a paid or an award ticket. He booked these flights as an award, so we only paid taxes on the tickets. It probably wouldn’t have been worth blowing double the amount of points we did for just a weekend getaway like that, but for the price of one award ticket with the Companion Pass, it was almost a no-brainer.

craterlake travelwitha9to5

Tips to make it work:

  • The Southwest Companion Pass is a great tool for slashing the prices of domestic flights. The easiest way to rack up the 110,000 points needed for the pass is by signing up for two of the Chase Southwest credit cards when the bonuses are at 50,000 points. These sign up bonuses count toward the 110,000 points needed.
  • Shop around for car rental options. I did a lot of searching before booking through Ultimate Rewards. The rate I found through Chase was cheaper than any I could find through online travel agents or directly through the car rental agencies, even when using private corporate booking codes.
  • I don’t recommend day tripping from Portland to Crater Lake as we did. It’s far, and most of the drive isn’t all that exciting. If you only have a short time and want to see Crater Lake, do an overnight and split the trip between two days.
  • On the other hand, the drive out to the coast is a quick and easy one from Portland. I definitely recommend adding it to your itinerary.
  • Cross-country weekend travel is possible. Our early morning flight out of Rochester, NY had us into Portland before noon, with most of the day to explore and a full day on Sunday. It’s really no worse than many weekend road trips when you crunch the numbers.


In case you’re making excuses about the cost, $235 = about two date nights out. Save your two date nights for a weekend getaway and get traveling!