$210 Cheap American Airlines flights Montego Bay (MBJ) to Chicago (ORD)

Apply the "Price (lowest to highest)" filter on Expedia to find cheap American Airlines round-trip flights from $334 from MBJ to ORD. Affordable one-way tickets from $210 are also on offer.**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 MBJ to ORD about one month before you want to go. The cheapest time to book 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. Regardless of fare class or itinerary, the best day of the week to book international airfare is usually Sunday. Friday can be the most expensive. Passengers booking 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.

Jetting off from MBJ at 1:15PM UTC-5, the earliest American Airlines flight to ORD arrives at 4:50PM UTC-6. Flying early means you're less likely to encounter cancellations or delays.* Not a morning person? The last American Airlines flight from MBJ to ORD departs at 3:23PM UTC-5 and touches down at 6:58PM UTC-6.*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.