This is live pricing from Travelpayouts' aggregation of 40+ booking engines. The $261 fare is the cheapest current round-trip from San Jose (SJC) to CHI on Southwest flight WN4252, departing 2026-05-22 at 22:55 with return on 2026-05-25.

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