This is live pricing from Travelpayouts' aggregation of 40+ booking engines. The $250 fare is the cheapest current round-trip from Chicago (MDW) to ORL on Southwest flight WN2924, departing 2026-10-12 at 20:40 with return on 2026-10-15.

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