Cheap flights to
Oregon

After years of watching the cost of airline tickets go up and down, we’ve figured out some trends that help travelers save money. We’ve found, for instance, a sweet spot before flights when most of the best deals happen. It’s 1-3 months before a domestic trip and 2-8 months before an international one. We call this sweet spot the Goldilocks Window.

There are, however, a few times when you’ll need to get your tickets before the standard Goldilocks Window to get the best fare. If your travel dates are inflexible, if you’re traveling over a big holiday, or if it’s the high season, you should add a few months to the equation for the best chance of scoring a great price. Keep in mind, too, that airlines almost always raise prices as the departure date nears, especially 21, 14, and 7 days before a flight—so you should always book your tickets before then.

Taking the most direct flight from your home airport to where you want to be may be convenient, but sometimes that convenience costs more than you want to pay. Before you buy a ticket, then, we recommend trying one of our favorite travel hacks: the Greek Islands Trick. The gist is that you find the best deal on a flight that gets you close (but not quite) to where you want to be and then find a separate flight (or train or boat) to get you the rest of the way. It’s an itinerary that requires more attention to detail on your part, but the savings may make that worth it.

The hack gets its name because it’s often significantly cheaper to fly into Athens and take a boat to the islands than it is to fly directly to the islands—but the Greek Islands Trick works for places all over the world. In the case of Oregon, you might want to compare fares to Seattle (SEA) with the cost of flights into Portland. Seattle’s airport is bigger than Portland’s, so you may find a cheaper flight to Sea-Tac. From there, it’s only about 2.5 hours by car to Portland. There are even buses that run between SEA and Portland for around $30.

The Greek Islands Trick has a counterpart on the departure end of a flight. Here, you’d check the fares flying from multiple airports (not just the one closest to you) to where you want to go. People who live in cities like New York or San Francisco are used to doing this, as they have several big airports in the area. But it’s a habit all travelers should get into, regardless of where they live. We see surprisingly low fares flying out of airports all over the country, both big hubs and little regional airports, so it behooves you to look around.

Travelers coming from Milwaukee might see fares into PDX in the neighborhood of $350 roundtrip, but zooming out on the map just a bit could reveal a ticket from Chicago for closer to $180 roundtrip. That kind of savings may make the 2-hour drive from Milwaukee look like a very smart idea.

Summer may be the popular time to travel for most people, since school is out and sunny weather makes so many adventures more pleasant, but that popularity means airlines can raise prices on airfare—sometimes by an enormous amount. Being flexible with your travel plans is one of the best ways to save money on a trip, which is one of the reasons budget travelers often schedule trips in the shoulder seasons or even the low season.

If you can’t avoid a high-season trip, though, there are still a few things you can do to save a bit on airfare. For summer vacations, try to book trips in the first two weeks of June or the last two weeks of August. These bookends to the season are among the cheapest summer weeks to fly. The most expensive days of the week to fly are generally Fridays and Sundays, so avoid those if you can. Shoot for Tuesdays, Wednesdays, and Saturdays, which are usually the cheapest days to fly.

Technology can feel at times like it’s making easy things more complex, but here’s a case of technology genuinely giving you back some of your precious free time. Rather than spending hours hunting for cheap airfare for that holiday, you’re trying to plan, sign up for a fare alert for the itinerary you want. You’ll get an email when the price goes down, so you’ll know when to buy tickets. If you’re considering multiple trips or dates, you’ll need to set up multiple alerts. Alternatively, you can join Going and let us put our years of airfare research to work for you.

Portland International Airport (PDX) is Oregon’s largest and busiest airport by a long shot. There are 67 airports around the United States with nonstop flights into PDX as well as airports in Canada, Germany, Iceland, Mexico, Netherlands, and the UK with direct flights to Portland. Portland is a hub for Alaska Airlines, which operates the most flights in and out of the city, and there are 17 other airlines also serving PDX.