Chicago (MDW) to Portland (PDX): 1,747 miles (2,811 km) great-circle, about 4h 00m nonstop by our estimate. Cheapest fare observed: $372 round-trip on Southwest, with 1 stop, departing June 25, 2026.
$372 round-trip, Southwest WN2862, departing 2026-06-25 at 18:40, returning 2026-07-07. The recorded itinerary left on a Thursday, returning on a Tuesday 12 nights later; the fare was observed 61 days before departure. "Book this flight" opens Kiwi.com with the same airline and dates.
At $372, it ranked 17th of the 30 round-trip fares we recorded from MDW (median $316). That is 21.3 cents per great-circle mile (round-trip price over one-way distance), close to the MDW median of 22.1 cents across 30 round-trip routes.
Routes from MDW of similar length: Los Angeles (1,747 mi) at $203 and Seattle (1,729 mi) at $210.
Southwest had the cheapest fare on 12 of 30 MDW routes. It is the 15th longest of the 30 routes we track from MDW.
Of 8 departure airports with a fare to Portland, Chicago (MDW) ranked 5th at $372. Lowest: $97 from Denver (DEN); highest: $462 from San Jose (SJC); 4 nonstop. Cheapest-fare airlines (routes): Alaska Airlines (2), American Airlines (2), Frontier (2) and Southwest (2).
The reverse, Portland (PDX) to Chicago (CHI), was $196 round-trip on Frontier, 1 stop, departing April 30, 2026. Portland to Chicago flights.
Travelpayouts fares (cheapest per route, observed April 25, 2026); OurAirports coordinates and elevations; IANA zones America/Chicago, America/Los_Angeles; flight time is our estimate.