Portland (PDX) to Chicago (CHI): 1,735 miles (2,792 km) great-circle, about 4h 00m nonstop by our estimate. Cheapest fare observed: $196 round-trip on Frontier, with 1 stop, departing April 30, 2026.
$196 round-trip, Frontier F91106, departing 2026-04-30 at 12:45, returning 2026-05-03. The recorded itinerary left on a Thursday, returning on a Sunday 3 nights later; the fare was observed 5 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $196, it was the cheapest of the 30 round-trip fares we recorded from PDX (median $378). That is 11.3 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: Houston (1,842 mi) at $249 and Dallas (1,614 mi) at $223.
Frontier had the cheapest fare on 7 of 30 PDX routes. It is the 21st longest of the 30 routes we track from PDX.
Of 33 departure airports with a fare to Chicago, Portland (PDX) ranked 17th at $196. Lowest: $89 from Atlanta (ATL); highest: $1241 from Nairobi (NBO); 16 nonstop. Cheapest-fare airlines (routes): Frontier (15), Spirit (5), United Airlines (4), American Airlines (2), airline 0O (1) and Alaska Airlines (1), plus 5 more.
Travelpayouts fares (cheapest per route, observed April 25, 2026); OurAirports coordinates and elevations; IANA zones America/Los_Angeles, America/Chicago; flight time is our estimate.