This is live pricing from Travelpayouts' aggregation of 40+ booking engines. The $229 fare is the cheapest current round-trip from Chicago (MDW) to BOS on Southwest flight WN1374, departing 2026-07-01 at 18:05 with return on 2026-07-06.

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