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Published June 27, 2026 by

Cheap Flights: Chicago to/from Kingston, Jamaica $397-$403 round-trip [September-October] – American Airlines

[06/27/2026 @ 11:26 AM CT] Deal time-stamp.
[2026-07-10 07:14:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

Deals are usually valid 24 to 72 hours after posting, but can expire at any time (see time-stamp).

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American Airlines has round-trip flights from Chicago (ORD) to Kingston, Jamaica (KIN) for $397-$403 with a connection. Flights September to October. Weekends available. Origin/Destination reversible.

American allows one carry-on bag and one personal item for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

If you use the Citi® / AAdvantage® Platinum Select® World Elite Mastercard® with AA flights, you get: a 25% inflight food and beverage discount, a $125 AA flight discount after you spend $20,000 or more in purchases during your card year, and your first checked bag is free on domestic American Airlines flights for you and up to four companions traveling on the same reservation.

You can usually save more money by booking your flight+hotel together as a package instead of separately.

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Kingston, Jamaica fares: [2026-07-10 07:14:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

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Ren P. Artemio

Ren P. Artemio

Ren is the Chief Director of Nap Times at Escape Houston, Escape ATX, Cheap DFW, and Escape Flights. He really likes researching airfare and the travel industry, especially when it means getting a cheap flight to anywhere (he's not picky).

Airfare Deals American Airlines Flights from Chicago / Milwaukee Jamaica Kingston Oneworld