This is live pricing from Travelpayouts' aggregation of 40+ booking engines. The $225 fare is the cheapest current round-trip from Chicago (MDW) to ORL on Southwest flight WN2763, departing 2026-09-11 at 19:50 with return on 2026-09-14.

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