This is live pricing from Travelpayouts' aggregation of 40+ booking engines. The $145 fare is the cheapest current round-trip from Chicago (MDW) to TPA on Southwest flight WN2669, departing 2026-05-01 at 20:30 with return on 2026-05-04. Total flight time is not specified, with non-stop routing.

Clicking "Book this flight" opens Kiwi.com with this exact flight pre-filtered — same airline, same dates, same passenger count. Kiwi aggregates availability across the major GDSs and low-cost carrier inventories, and confirmation is instant once payment clears. Free cancellation typically available within 24 hours under most airline policies.

Prices on this route historically range $123–$247 depending on season, day of week, and booking lead time.