This is live pricing from Travelpayouts' aggregation of 40+ booking engines. The $190 fare is the cheapest current round-trip from Chicago (MDW) to MIA on Southwest flight WN199, departing 2026-08-15 at 06:45 with return on 2026-08-19.

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