How I Did It: A $1,300 Trip to Oregon for $22.50

By: Dillon Carter

Hey guys!

I recently got back from a four-day trip to Oregon with my girlfriend. From hot springs to waterfalls to snow capped mountains, it was was an amazing adventure.

I had been sitting on some points for a while and finally had a short break from class, so we quickly decided to book a trip. The whole booking process took less than an hour.

Dillon's Trip

As everyone knows, trying to make time to travel can be particularly frustrating, so we booked this three months in advance. As a budding entrepreneur, this gave me enough lead time to ensure I had everything in place so I could relax on my vacation.

For those who don’t think you can take the time away from work, I’m here to tell you that it is possible. With a little planning, you can not only take a great vacation, but enjoy it too!

Dillon's Trip

How I try to sleep on a six hour flight at 6am

In total, we took six flights over the course of 5 days to get from Florida to Oregon and back. Thanks to this experience, I now know that I’m terrible at sleeping on planes.

Even after staying up the night before our 6am flight (for some reason), I still couldn’t sleep.

Pro-tip: staying awake for 28 hours is a terrible idea. Don’t do it.

Who knew it would be such a journey to fly from Florida to a small city in Oregon…


Here’s How We Did It

To book our flights and lodging, we used the following points:

  • Capital One Venture – 50,000 points
  • Chase UR (transferred to United) – 40,000 points

We flew from JAX (Jacksonville, FL) to EUG (Eugene, OR) with connections in EWR (Newark, NJ) and SFO (San Francisco, CA) along the way. As you can see below, we used the same routing on our return.

Dillon's Trip

We often talk about the benefits of being flexible, and this trip was a great reminder of that. With two connections needed, it wasn’t the most direct path, but it fit our needs.

Rather than getting a hotel, we opted to stay in a cabin we found on Airbnb that we found so we could use some of my Capital One Venture points.

This wasn’t just an area without hotels. There wasn’t even internet or cell service in the area.

Because our cabin was an hour away from the airport, we needed to rent a car. I’m 24 and my girlfriend is 21, so we weren’t going to get the best rates. The total cost for the rental car was $248 for just three days. Luckily, my Capital One Venture points came in handy and I was able to “erase” that charge the day it posted.

So, let’s review how how each part of this trip was paid for with points:

1. Flights 

Our flights were quite easy and we had them booked within a day or so. The only small delay was transferring points from Chase UR to my United account. It took 40,000 United miles to get us both there and back with a $22.50 fee which ended up being the only actual expense for this trip that I couldn’t use points on.

Dillon's Trip

The total cost for our round trip flights if we didn’t use points

2. Airbnb 

We easily found a great cabin with a ton of reviews that seemed perfect. We had a completely private cabin that stood over a rushing river with a full kitchen.

Dillon's Trip

How we ate breakfast our last morning at the cabin

They even had a collection of dvds that included Harry Potter! +5 points to Gryffindor.

The Airbnb was completely free thanks to my Capital One Venture points.

Dillon's Trip Cost

3. Rental Car 

I already went over this a bit before, but the total cost for a rental car for 3 days would have been $248, but was quickly paid off with Venture points the day the charge posted.


What Does This Mean For You?

I’m a broke college student starting a business and, because of miles and points, I was able to take my girlfriend on a transcontinental adventure for $22.50. If I can do this, you better believe you can do it too.

Where will your next adventure take you?

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