Mother-Daughter Trip to Oregon: Part 1 – Introduction and Planning

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Visiting family and friends is my favorite way to use miles and points!

Family visits may not have the same lucrative redemption rates as a trip in First Class, or foreign 5-star hotels.  But the memories I make are priceless!

I recently spent some much-needed time with my mom in the beautiful state of Oregon!  I spent a few days in Portland with my friend Kristen before my mom arrived.

The highlight of my travel was road-tripping with my mom to my cousin Rachel’s wedding.  The wedding was a long overdue family reunion.  I hadn’t seen some of my cousins for years!

The drive along the Oregon coast was gorgeous.  It’s now one of my favorite places in the US!

Mother-Daughter Trip to Oregon Index:

• Part 1 – Introduction and Planning
• Part 2 – Discovering Portland
• Part 3 – Discovering the Oregon Coast

Booking Award Flights on Southwest and Delta

I had originally planned on flying into Seattle, Washington, and driving to Portland, Oregon.  My plans changed last-minute, so I flew in and out of Portland (definitely the more expensive option!).

I booked my round-trip flight from Austin, Texas, to Portland, Oregon using Southwest points.  I ended up paying ~26,000 points and ~$11 in taxes and fees round trip.  My original cost was closer to 19,000 points, but my plans changed at the last minute.  I love Southwest because you can cancel for “free”, but realize that it may cost more points to book a new flight.

My mom flew to Portland with Delta.  Her round-trip ticket in coach from Traverse City, Michigan, to Portland was 35,000 miles and ~$11 in taxes and fees.

That brought our total of 2 round-trip tickets to Oregon for less than $25!!  That’s a steal!

Compare Rental Car Options for the Cheapest Prices

It pays to shop around for the cheapest car rental prices.  Different websites can have very different rates.  Check out our series on how to book car rentals for cheap to find the best prices.

I used Hotwire to book my rental car.  The cost for 7 days was a whopping $385 (thanks to $115 in taxes!).  That’s quite a bit more than I would have liked to pay, but the best deal I could find.  Since I saved so much on the flights,  I was more comfortable paying for an expensive rental car (plus I didn’t have much of a choice).

Couchsurfing in Portland!

There are lots of housing options in Portland (and along the beautiful coast, too).  Great hotels, Airbnbs, even Couchsurfing!

I enjoy staying at luxury hotels just as much as the next girl.  But I also love staying in residential areas through sites like Airbnb, because I get to meet locals and hear their stories (like during my recent trip to Cuba!).  It brings a new dimension to traveling!

Here’s how to choose a nice, safe Airbnb, and my tips on how to negotiate a better price!

My friend, Kristen, and I decided to try Couchsurfing, which is similar to Airbnb, and a great way to meet locals.  And it’s free.  You can contact a host through the Couchsurfing website.

Our host was a professional chef!  We were given 5-star breakfasts every morning.

Some “couches” are actually private bedrooms.  Hosts describe their home and sleeping arrangements in their profile, and you can use a filter for specific sleeping arrangements (like a private room).  And travelers post reviews of their hosts, which makes stepping into a stranger’s house less worrisome!

My mom and I stayed at a hotel in Coos Bay for the wedding, and then at my cousin’s house in Albany.

You Can Do It, Too!

Flights

Link:  How to Transfer Chase Ultimate Rewards Points to Southwest

Link:  How to Earn the Southwest Companion Pass

Booking domestic award flights are easy, and generally won’t cost an outrageous amount of points.  Especially if you’re flying to a city served by lots of airlines, like Portland, Oregon.  Check to see what airline is most convenient for you from your home airport to help you decide which miles & points you should collect for the travel you have in mind.

It’s easy to get to Portland on Southwest.  If you have cards like the Chase Sapphire Preferred Card, Chase Sapphire Reserve, Chase Ink Plus (no longer available), or Chase Ink Bold (no longer available), you can transfer Chase Ultimate Rewards points to travel partners like Southwest.  And if you have the Southwest Companion Pass, you can bring a friend for (almost) free!

You can also earn lots of Southwest points by signing-up for the Southwest Rapid Rewards® Plus Credit Card, Southwest Rapid Rewards® Premier Credit Card, and the Southwest Rapid Rewards® Premier Business Credit Card.

Accommodations

There are plenty of hotels to stay at with points in Oregon, especially in Portland.  The Nines Hotel in downtown Portland has a great location with incredible food and a beautiful rooftop restaurant.  And it’s bookable with Starwood points!

If you’d rather save points (or money), consider searching Airbnb for homes near your ideal location.  And peek at the reviews to ensure the host is reliable and trustworthy.

Use the Couchsurfing website to search for homes near the location you want to stay.  Use the filters to find an acceptable sleeping arrangement (private room, shared room, etc.) and read reviews to make sure it’s a good fit.

Bottom Line

Traveling to spend time with friends and family is my favorite use of miles & points.  I loved being reunited with my cousins who I haven’t seen in years!  Exploring a new part of the US with my mom was so much fun!

Flying to Portland cost me less than $25 in cash and ~60,000 points for both me and my mom.  We used a combination of Southwest points and Delta miles.

My friend and I tried Couchsurfing on this trip, and we’re really glad we did.  It was fun to meet a local; we felt like we had a private tour guide!  If Couchsurfing doesn’t sound appealing to you, you can stay at hotels with points (or cash, of course), or consider staying at an Airbnb.