Portland (PDX) to Orlando (ORL): 2,525 miles (4,063 km) great-circle, about 5h 35m nonstop by our estimate. Cheapest fare observed: $279 round-trip on Southwest, with 1 stop, departing May 9, 2026.
$279 round-trip, Southwest WN3555, departing 2026-05-09 at 12:20, returning 2026-05-16. The recorded itinerary left on a Saturday, returning on a Saturday 7 nights later; the fare was observed 14 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $279, it ranked 10th of the 30 round-trip fares we recorded from PDX (median $378). That is 11.1 cents per great-circle mile (round-trip price over one-way distance), below the PDX median of 21.2 cents across 30 round-trip routes.
Routes from PDX of similar length: Boston (2,530 mi) at $331 and Tampa (2,494 mi) at $211.
Southwest had the cheapest fare on 2 of 30 PDX routes. It is the 12th longest of the 30 routes we track from PDX.
Of 31 departure airports with a fare to Orlando, Portland (PDX) ranked 21st at $279. Lowest: $61 from Charlotte (CLT); highest: $754 from Panama City (PTY); 14 nonstop. Cheapest-fare airlines (routes): Frontier (13), Spirit (5), Southwest (3), Air Canada (1), Arajet (1) and Avianca (1), plus 7 more.
Travelpayouts fares (cheapest per route, observed April 25, 2026); OurAirports coordinates and elevations; IANA zones America/Los_Angeles, America/New_York; flight time is our estimate.