This is live pricing from Travelpayouts' aggregation of 40+ booking engines. The $500 fare is the cheapest current round-trip from Chicago (ORD) to EYW on American Airlines flight AA3954, departing 2026-08-08 at 12:00 with return on 2026-08-15.

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