American Airlines has round-trip flights from Portland (PDX) to Chicago (ORD) for $179, NONSTOP. Flights in May. Very few weekends available. Origin/Destination reversible.
Category: <span>Flights from Portland</span>
Image Credits: Daniel Schwen, Creative Commons 4.0
British Airways and Finnair have round-trip flights from Portland (PDX) to Amsterdam (AMS) for $481-$491 with a connection. Flights September to March. Departures on Monday, Tuesday, and Wednesday. 7-day minimum stay required.
Southwest, American, and Delta have round-trip flights to/from various destinations in the USA at a discount today for $97-$189, NONSTOP or with a connection. Dates vary, use the linked calendar. Flights are mostly on Tuesdays, Wednesdays, and Saturdays. Origin/Destination reversible.
Image Credits: Damian Gadal, Creative Commons 2.0 (flickr)
Southwest, United, and American Airlines have round-trip flights from Portland (PDX) to Santa Barbara (SBA) for $125-$161 with a connection. Flights May to November. Extended weekends available. Origin/Destination reversible. No Thanksgiving dates.
Image Credits: yeowatzup, Creative Commons 2.0
Southwest has round-trip flights from Portland (PDX) to Orlando (MCO) for $160-$183 with a connection. Flights August to November. Extended weekends available. Origin/Destination reversible. No Thanksgiving dates.
Image Credits: Larry Johnson, Creative Commons 2.0
Southwest has round-trip flights from Portland (PDX) to Phoenix or Denver (PHX, DEN) for $141-$172, NONSTOP. Phoenix flights May to July. Denver flights May to June. Very few weekends available. Origin/Destination reversible.
Icelandair has round-trip flights from Portland (PDX) to Amsterdam or Paris (AMS, CDG) for $528-$600 with a connection. Amsterdam flights in August, October, November, December, and March. Paris flights August to October. Holiday blackouts.
Some small OTAs on Skyscanner have this for as low as $500; which is cheaper than the airline. If you plan on booking there, beware of any site that charges a fee to cancel a ticket within the 24-hour “free” period. Use unknown booking sites at your own risk.
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This post is the unfiltered daily Patreon recap of New York, Los Angeles + metro area, Chicago, Milwaukee, Seattle, Everett, and Portland airfare as of May 04, 2025 @ 02:38 PM Central Time. There are currently (1252) fares that are below (or near) their 6-month moving average.
The (1252) fares found today are more than the 30-day average of (1167) per day. This means that deal availability is trending up.
The airfare count per region is as follows:
New York/Newark (291)
Los Angeles area (360)
Chicago/Milwaukee (219)
Seattle/Everett (195)
Portland (187)
Image Credits: martin_vmorris, Creative Commons 2.0 (Flickr)
United has round-trip flights from Portland (PDX) to Shannon (SNN) for $486-$536 with a connection. Flights July to September. 7-day minimum stay required.
Image Credits: Giuseppe Milo, Released under Creative Commons 2.0 (flickr)
Icelandair has round-trip flights from Seattle or Portland (SEA, PDX) to Reykjavik (KEF) for $447-$460, NONSTOP. Flights departing Seattle September to February. Flights departing Portland September to November.
Some small OTAs on Skyscanner have this for as low as $424; which is cheaper than the airline. If you plan on booking there, beware of any site that charges a fee to cancel a ticket within the 24-hour “free” period. Use unknown booking sites at your own risk.
Image Credits: Akrobaten gang og sykkelbro, Creative Commons 3.0
Icelandair has round-trip flights from Portland (PDX) to Stockholm, Rome, Paris, Oslo, London, Helsinki, or Copenhagen (ARN, FCO, CDG, OSL, LHR, HEL, CPH) for $468-$573 with a connection. Flights October to December. No Christmas dates available.
Some small OTAs on Skyscanner have this for as low as $440; or about -$25 less than the price published by the airline. If you plan on booking there, beware of any site that charges a fee to cancel a ticket within the 24-hour “free” period. Use unknown booking sites at your own risk.
London and Paris are the most expensive fares in this list.
Image Credits: Donaldytong, CC-BY-SA-3.0
Icelandair has round-trip flights from Portland (PDX) to Dublin (DUB) for $394 with a connection. Flights October to December. No Christmas dates available.
Image Credits: Rambla, Creative Commons 2.0 (wikipedia)
British Airways and Iberia have round-trip flights from Portland (PDX) to Barcelona (BCN) for $541-$555 with a connection. Flights September to February. Departures on Monday, Tuesday, Wednesday, and Sunday. 7-day minimum stay required.
Image Credits: Cacophony, Creative Commons
United has round-trip flights from Chicago (ORD) to Portland, Oregon (PDX) for $179-$187, NONSTOP. Flights in May. Very few weekends available. Origin/Destination reversible.
Alaska Airlines has round-trip flights from Portland (PDX) to Liberia, Costa Rica (LIR) for $361 with a connection. Flights September to October. Departures on Monday, Tuesday, and Wednesday. Origin/Destination reversible.
Some small OTAs on Skyscanner have this for as low as $346; which is cheaper than the airline. If you plan on booking there, beware of any site that charges a fee to cancel a ticket within the 24-hour “free” period. Use unknown booking sites at your own risk.
A Carry-on bag and also a personal item is allowed for free on Alaska Airlines. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Image Credits: Jaegar Moore, Creative Commons 2.0 (flickr)
Southwest has round-trip flights from Portland (PDX) to San Jose, Sacramento, or Oakland (SJC, SMF, OAK) for $77, NONSTOP. Flights May to August. No Weekends. Departures on Monday, Tuesday, Wednesday, and Thursday. Origin/Destination reversible.
This is likely part of a larger sale that Southwest will announce tomorrow 04/22 (probably).
British Airways, Finnair, and Iberia have round-trip flights from Portland (PDX) to Amsterdam (AMS) for $613 with a connection. Flights April, May, and August. Departures on Monday, Tuesday, Wednesday, and Sunday. 7-day minimum stay required. Limited date selection.
Image Credits: Ricardo Diaz, Creative Commons 2.0
United has round-trip flights from Portland (PDX) to Cancun (CUN) for $324-$340 with a connection. Flights April to February. Weekends available. Origin/Destination reversible.
Outbound departing flight is a late-night departure.
Image Credits: Thomas Hawk, Creative Commons 2.0 (flickr)
American Airlines has round-trip flights from Portland (PDX) to New York, Detroit, Minneapolis, or Atlanta (JFK, DTW, MSP, ATL) for $159-$173 with a connection. Flights April, May, August, September, October, and November. No Thanksgiving dates.
A Carry-on bag and also a personal item is allowed for free on American. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.
Image Credits: Plashing Vole, Creative Commons 2.0 (flickr)
United has round-trip flights from Portland (PDX) to Austin (AUS) for $170-$179 with a connection. Flights April to February. Weekends available.
United’s “Basic Economy” fares do not allow for a free carry-on bag. Only a personal item (like a small laptop bag) is free. Seats are randomly assigned for free prior to boarding.