This is live pricing from Travelpayouts' aggregation of 40+ booking engines. The $253 fare is the cheapest current round-trip from Chicago (MDW) to HOU on Southwest flight WN2757, departing 2026-07-09 at 12:20 with return on 2026-07-12.

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