Three Days In Portland on Points

Portland in the summer is an overly popular destination for many, especially for the millennial crowd.  Portland is one of the up and coming cities where tons of millenials are flocking towards.  An estimated of 300 people move to Portland everyday.  It was our first time in Portland and we were able to spend three days in Portland on points to see what the fuss was about.

We flew to Portland on Southwest points, which we accumulated with the Chase Sapphire Preferred and Chase Southwest credit cards.  We spent a little more Southwest points than we would have liked because we needed to travel at exact times.  However, many times you can find sales where you can fly from Los Angeles to Portland for about 6,000 points one-way.  We stayed at the new Hilton Duniway Portland Hotel for 40,000 points per night for two nights and one night at the Radisson PDX Airport hotel for 28,000 Club Carlson points.  My other highly recommended hotel choice would be the Hyatt Place Portland Downtown for only 12,000 Hyatt points per night.

The Hilton Duniway Portland Hotel is a modern boutique hotel in the center of Portland’s downtown.  Usually hotels like this would cost many points or have an expensive nightly rate. The nightly rate was about $220 when I checked, so 40,000 Hilton points from my AMEX Hilton Surpass credit card was a great deal.  Perhaps an incentive to stay at this hotel is that you can have a great breakfast at the Jackrabbit restaurant, which features awesome dishes like a gourmet chicken and waffles.

JackRabbit Breakfast

JackRabbit Breakfast

Things to Do in Portland

We didn’t rent a car in Portland and you don’t really need to unless you want to venture out of the city.  The $5 day pass is an incredible deal and even works to and from the airport.  Even the top site Multonomah Falls, we took a $5 roundtrip shuttle there.

Forest Park Hike to Pittock Mansion – This was about a 3 mile hike one-way from Lower Mackinley Park to Pittock Mansion.  Currently in the summer of 2017, Lower Mackinley Park is closed, so we started from Hollman Park Entrance and hiked all the way to Pittock Mansion via Wildwood Travel.  We took Bus 15 from downtown.  It was a beautiful hike in the forest and passed by an abandoned house called the Witch’s Hut. Pittock Mansion is at the end of the hike of Wildwood travel and it features nice views of downtown Portland.  You can hike back and catch the bus again, but we just took a $10 Lyft ride back to the hotel for the sake of time.

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Foodie Crawl – Portland is the ultimate foodie city when it comes to coffee, beer, and farm to table food.  The top place for ice cream is definitely Salt and Straw.  When it comes to coffee, Barista serves the best quality lattes, in my opinion.  Heart Coffee Roasters is a close second.

Latte from Barista

Latte from Barista

There are also tons of farm to table restaurants you can find on Yelp, but we tried the very popular Tasty n Alder. The flat iron steak was awesome, highly recommended.  It can be a busy restaurant and they don’t take reservations, so show up at 5:30PM.

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Blue Star donuts serves gourmet fresh donuts.  It was a great tasting donut, but a little overrated considering the price($3-$4) to be honest.


Pine State Biscuits is an awesome breakfast place to get biscuits and gravy or biscuits with bacon/sausage/egg/etc.  Prices were quite reasonable.


Multonomah Falls is a must do in Portland.  In the summer, you can take a $5 roundtrip shuttle to the falls from Gateway Transit Center.  It’s quite convenient and you can not worry about parking.  The view of the falls is amazing and the hike to the falls is a good 1.2 mile challenge each way.  There are other hikes nearby, but if you are short on time you can just go see the falls.

Multnomah Falls

Multnomah Falls

Overall, Portland is a great city to visit and relatively cheaper than other big US cities.  There is also no sales tax, which is great.  It’s a good place to use Hyatt or Hilton points for a stay or you can stay at a local AirBnB. We visited in the summer, which had very similar weather to SoCal, so it was great to us.  I can’t see myself living there like many other transplants because of the rainy weather most of the year.  Also, the freeways are quite congested because the amount of people moving in is overcrowding the freeways.  It was still awesome to spend three days in Portland on points!


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