Cheap flights from Portland

We are watching 73 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 Oakland €69 San Francisco €71

The booking happens on our partner site. The price you see there is the price you pay; they pay us, you do not.

Get the cheapest flights from Portland, every week

Free. One email a week, or one per real drop on a route you pick. Unsubscribe in one click.

Where to fly from Portland

Fri

8 Jan

Portland → San Diego

Alaska Airlines Based on 161 observations ✈ Direct

Southwest Airlines Based on 128 observations ✈ Direct

€69

Mon

23 Nov

Portland → San Francisco

Alaska Airlines Based on 194 observations ✈ Direct

€71

Tue

8 Dec

Portland → Los Angeles

Frontier Airlines Based on 197 observations ✈ Direct

€73

Tue

8 Dec

Portland → Long Beach

AS Based on 89 observations 1 stop

Alaska Airlines Based on 60 observations ✈ Direct

SeaPort Airlines Based on 185 observations ✈ Direct

Frontier Airlines Based on 121 observations ✈ Direct

American Airlines Based on 41 observations 1 stop

Frontier Airlines Based on 160 observations 1 stop

F9 Based on 54 observations ✈ Direct

Air Canada Based on 116 observations ✈ Direct

Frontier Airlines Based on 108 observations 1 stop

Alaska Airlines Based on 51 observations 1 stop

€111

Mon

4 Jan

Portland → Fort Lauderdale

AS Based on 100 observations 1 stop

AS Based on 75 observations ✈ Direct

Southwest Airlines Based on 43 observations 1 stop

€131

Mon

9 Nov

Portland → Salt Lake City

Frontier Airlines Based on 78 observations 1 stop

Alaska Airlines Based on 47 observations 1 stop

Southwest Airlines Based on 67 observations 1 stop

€142

Thu

12 Nov

Portland → Dallas-Fort Worth

Frontier Airlines Based on 45 observations 1 stop

€144

Tue

10 Nov

Portland → Minneapolis

Frontier Airlines Based on 39 observations 1 stop

Hawaiian Airlines Based on 364 observations ✈ Direct

HA Based on 201 observations ✈ Direct

Frontier Airlines Based on 49 observations 3 stops

€182

Wed

2 Dec

Portland → Washington

Frontier Airlines Based on 53 observations 1 stop

€189

Mon

7 Dec

Portland → Copenhagen

Icelandair Based on 21 observations 1 stop

Frontier Airlines Based on 50 observations 2 stops

American Airlines Based on 10 observations 1 stop

Frontier Airlines Based on 12 observations 1 stop

€204

Fri

13 Nov

Portland → Santa Rosa

Southwest Airlines Based on 11 observations 1 stop

Alaska Airlines Based on 9 observations ✈ Direct

Southwest Airlines Based on 13 observations 1 stop

Alaska Airlines Based on 20 observations 1 stop

€214

Tue

1 Dec

Portland → Kailua-Kona

Southwest Airlines Based on 9 observations 1 stop

€214

Sun

15 Nov

Portland → Raleigh/Durham

Frontier Airlines Based on 38 observations 1 stop

American Airlines Based on 15 observations 1 stop

Alaska Airlines Based on 25 observations ✈ Direct

Alaska Airlines Based on 25 observations ✈ Direct

Alaska Airlines Based on 15 observations ✈ Direct

Alaska Airlines Based on 27 observations ✈ Direct

Icelandair Based on 9 observations 1 stop

Icelandair Based on 41 observations 2 stops

Air Canada Based on 22 observations 1 stop

Icelandair Based on 57 observations 1 stop

Alaska Airlines Based on 17 observations ✈ Direct

€249

Thu

26 Nov

Portland → Punta Cana

Air Canada Based on 12 observations 2 stops

€252

Fri

13 Nov

Portland → Bellingham

Alaska Airlines Based on 21 observations ✈ Direct

Icelandair Based on 94 observations 3 stops

Icelandair Based on 11 observations 2 stops

Icelandair Based on 16 observations 3 stops

Icelandair Based on 66 observations 2 stops

United Airlines Based on 33 observations 2 stops

Alaska Airlines Based on 9 observations ✈ Direct

Icelandair Based on 19 observations 3 stops

€289

Mon

16 Nov

Portland → Sharm El Sheikh

Icelandair Based on 13 observations 3 stops

Alaska Airlines Based on 11 observations 1 stop

Icelandair Based on 19 observations 2 stops

Alaska Airlines Based on 32 observations ✈ Direct

Alaska Airlines Based on 8 observations 2 stops

€296

Flights from Portland: quick answers

What is the cheapest flight from Portland right now?

San Diego at €55 one-way, the lowest fare today across the 73 routes we track from Portland. Next: Oakland €69, San Francisco €71, Los Angeles €73.

What is the cheapest month to fly from Portland?

December. On the 27 routes from Portland where we measured it, December fares were typically 5% below the route's median month.

How far in advance should I book flights from Portland?

0–13 days before departure: that has been the cheapest booking window on 16 of the 51 routes from Portland where we measured it.

Which airlines have the cheapest flights from Portland?

Alaska Airlines has the lowest fare on 21 of the 73 routes we track from Portland, then Frontier Airlines (15), Icelandair (14), Southwest Airlines (6), American Airlines (5).

How many routes from Portland does Piratefly track?

73 routes, with 3,870 fares we have recorded over time.

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 (97,668 flights on 19,841 routes, 2026-06-14 to 2026-11-05), that window had the smallest average premium over each flight's lowest fare: +16.7%, 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 +3.5% and Tuesday +4.3%, 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 January 2027 was the dearest at +22.7%. Covers September 2026, October 2026, November 2026, December 2026, January 2027; fares observed 2026-06-14 to 2026-11-05.