This is live pricing from Travelpayouts' aggregation of 40+ booking engines. The $305 fare is the cheapest current round-trip from Chicago (MDW) to SAN on Southwest flight WN2884, departing 2026-07-30 at 21:10 with return on 2026-08-04.

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