This is live pricing from Travelpayouts' aggregation of 40+ booking engines. The $372 fare is the cheapest current round-trip from Chicago (MDW) to PDX on Southwest flight WN2862, departing 2026-06-25 at 18:40 with return on 2026-07-07.

Clicking "Book this flight" opens Kiwi.com with this exact flight pre-filtered — same airline, same dates, same passenger count.