This is live pricing from Travelpayouts' aggregation of 40+ booking engines. The $159 fare is the cheapest current round-trip from Chicago (MDW) to MIA on Southwest flight WN4242, departing 2026-09-14 at 08:00 with return on 2026-09-17.

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