This is live pricing from Travelpayouts' aggregation of 40+ booking engines. The $150 fare is the cheapest current round-trip from Chicago (MDW) to SJU on Southwest flight WN1417, departing 2026-08-16 at 20:05 with return on 2026-08-24.

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