$303 Cheap American Airlines flights Chicago (ORD) to Basseterre (SKB)

Grab budget-friendly return American Airlines flights from $566 from ORD to SKB by organizing your results from "Price (lowest to highest)" on Expedia. Or search for options from $303 for a one-way journey.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Search for American Airlines flights from ORD to SKB about one month before you want to leave. The cheapest time to reserve an international flight is generally 18 to 29 days ahead of your travel date when you can save 17% versus booking four to five months in advance. No matter your itinerary or fare class, the best day of the week to book international airfare is usually Sunday. Friday is often the most expensive. Passengers booking on a Sunday can save an average of 17% compared to those who book on a Friday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.

Browse American Airlines's earliest flights from ORD to SKB by selecting the "Early Morning" and "Morning" filters. Not only will you get to where you're going sooner, early departures also experience 20% fewer cancellations.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.