This is live pricing from Travelpayouts' aggregation of 40+ booking engines. The $145 fare is the cheapest current round-trip from Chicago (MDW) to NYC on Southwest flight WN806, departing 2026-10-10 at 11:25 with return on 2026-10-12.

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