$283 Cheap American Airlines flights Chicago (ORD) to St. Thomas (STT)

Set the "Price (lowest to highest)" filter on Expedia to search for cheap American Airlines return flights from $505 from ORD to STT. Affordable one-way fares from $283 are available too.**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.

Look for American Airlines flights from ORD to STT about one month before you want to leave. The cheapest time to reserve an international flight is usually 18 to 29 days ahead of your travel date when you can save 17% versus booking four to five months in advance. Regardless of itinerary or fare class, the best day to book international airfare is usually Sunday. Friday can be the most expensive. Travelers who book on a Sunday can save 17% on average 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.

Leaving ORD at 8:35AM UTC-6, the first American Airlines flight to STT lands at 3:20PM UTC-4. Traveling early means you're less likely to experience delays.* Don't like early starts? The last American Airlines flight from ORD to STT departs at 8:35AM UTC-6 and touches down at 3:20PM UTC-4.*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.