Piratefly

Cheap flights from Portland

We are watching 67 routes out of Portland. The cheapest fare we can vouch for today is €55, and for each one we say whether today is a good moment or you should wait.

See this fare · San Diego €55

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Where to fly from Portland

Portland → San Diego

Alaska Airlines Based on 159 observations ✈ Direct

Portland → San Francisco

United Airlines Based on 189 observations ✈ Direct

Portland → Oakland

Southwest Airlines Based on 122 observations ✈ Direct

Portland → San Jose

Alaska Airlines Based on 58 observations ✈ Direct

Portland → Seattle

SeaPort Airlines Based on 163 observations ✈ Direct

Portland → Las Vegas

Frontier Airlines Based on 109 observations ✈ Direct

Portland → Fresno

American Airlines Based on 34 observations 1 stop

Portland → Long Beach

Southwest Airlines Based on 86 observations ✈ Direct

Portland → Phoenix

Frontier Airlines Based on 157 observations 1 stop

Portland → Ontario

Frontier Airlines Based on 103 observations 1 stop

Portland → Los Angeles

Alaska Airlines Based on 191 observations 1 stop

Portland → Vancouver

Air Canada Based on 113 observations ✈ Direct

Portland → Everett

Alaska Airlines Based on 47 observations 1 stop

Portland → Boise

Southwest Airlines Based on 41 observations 1 stop

Portland → Salt Lake City

Frontier Airlines Based on 76 observations 1 stop

Portland → Denver

Frontier Airlines Based on 50 observations 1 stop

Portland → Atlanta

Alaska Airlines Based on 42 observations 1 stop

Portland → New York

Frontier Airlines Based on 348 observations 3 stops

Portland → Dallas-Fort Worth

Frontier Airlines Based on 43 observations 1 stop

Portland → Minneapolis

Frontier Airlines Based on 34 observations 1 stop

Portland → Austin

Alaska Airlines Based on 12 observations ✈ Direct

Portland → Honolulu

Alaska Airlines Based on 189 observations ✈ Direct

Portland → Chicago

American Airlines Based on 59 observations ✈ Direct

Portland → Guadalajara

Alaska Airlines Based on 73 observations 1 stop

Portland → Newburgh

Frontier Airlines Based on 47 observations 3 stops

Portland → Washington

Frontier Airlines Based on 47 observations 1 stop

Portland → Copenhagen

Icelandair Based on 19 observations 1 stop

Portland → Baltimore

Frontier Airlines Based on 46 observations 2 stops

Portland → Tucson

American Airlines Based on 8 observations 1 stop

Portland → Miami

Frontier Airlines Based on 63 observations 2 stops

Portland → Santa Rosa

Southwest Airlines Based on 9 observations 1 stop

Portland → Spokane

Alaska Airlines Based on 18 observations 1 stop

Portland → Kailua-Kona

Southwest Airlines Based on 9 observations 1 stop

Portland → Raleigh/Durham

Frontier Airlines Based on 37 observations 1 stop

Portland → Medford

Alaska Airlines Based on 23 observations ✈ Direct

Portland → Pasco

Alaska Airlines Based on 23 observations ✈ Direct

Portland → Eugene

Alaska Airlines Based on 13 observations ✈ Direct

Portland → Redmond

Alaska Airlines Based on 22 observations ✈ Direct

Portland → Charlotte

Southwest Airlines Based on 9 observations 2 stops

Portland → London

Icelandair Based on 39 observations 2 stops

Portland → Calgary

Air Canada Based on 20 observations 1 stop

Portland → Munich

Icelandair Based on 55 observations 1 stop

Portland → Kalispell

Alaska Airlines Based on 15 observations ✈ Direct

Portland → Punta Cana

Air Canada Based on 10 observations 2 stops

Portland → Bellingham

Alaska Airlines Based on 19 observations ✈ Direct

Portland → Paris

Icelandair Based on 88 observations 3 stops

Portland → Milan

Icelandair Based on 9 observations 2 stops

Portland → Dortmund

Icelandair Based on 16 observations 3 stops

Portland → Amsterdam

Icelandair Based on 66 observations 2 stops

Portland → Boston

United Airlines Based on 31 observations 2 stops

Portland → Fort Lauderdale

United Airlines Based on 95 observations 1 stop

Portland → Suceava

Icelandair Based on 17 observations 3 stops

Portland → Sharm El Sheikh

Icelandair Based on 11 observations 3 stops

Portland → Yakima

Alaska Airlines Based on 9 observations 1 stop

Portland → Bucharest

Icelandair Based on 11 observations 2 stops

Portland → Vienna

Icelandair Based on 8 observations 2 stops

Portland → Sioux Falls

Frontier Airlines Based on 27 observations 2 stops

Portland → Arcata/Eureka

Alaska Airlines Based on 12 observations 1 stop

Portland → Cancún

Frontier Airlines Based on 72 observations 2 stops

Portland → Anchorage

Alaska Airlines Based on 28 observations ✈ Direct

Booking tips from our fare data

How far in advance should you book a flight?: Book 1–1.5 months before departure. Tracking the same flights at every lead time (92,167 flights on 19,004 routes, 2026-06-14 to 2026-11-03), that window had the smallest average premium over each flight's lowest fare: +16.8%, against +49.3% in the last 3 days.
What is the cheapest day of the week to fly?: Wednesday. Comparing each fare with the median of its own route, Wednesday departures were +3.3% and Tuesday +4.1%, while Friday was the dearest at +10.5%. Weekend departures cost more than midweek ones.
What is the cheapest month to fly?: November 2026. Comparing each route's fares month by month (booked 8–60 days ahead), November 2026 departures were -1.1% against the route's own median, while September 2026 was the dearest at +6.2%. Covers September 2026, October 2026, November 2026, December 2026; fares observed 2026-06-14 to 2026-11-03.

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