Cheap flights from Illinois to Jamaica from $160

The cheapest month to fly to Jamaica from Illinois is in December. Flight prices, which tend to average around $84, are often lower during this time because this is during the off-season. If you aren’t able to travel to Jamaica during the month of December, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $93.

The cheapest day to depart on your flight to Jamaica is on a Tuesday when prices can be found for as low as $492. This is often the case because there is less demand to fly during this day of the week. On the other hand, Thursday is the most expensive day to depart from Illinois because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $622.

Fly from Chicago O'Hare Intl to Montego Bay Sangster Intl for the best Illinois - Jamaica flight prices

You are more likely to see cheaper flights to Jamaica from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Jamaica for around $523 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Jamaica from Illinois for as low as $466 on momondo.

There are 2 cabin classes available to choose from on Illinois to Jamaica flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 20% on your flight if you consider stops on a Illinois to Jamaica flight.

JetBlue, American Airlines, and Delta are the most popular carriers operating from Illinois to Jamaica

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Jamaica from Illinois according to our data. American Airlines is the first choice among our users, with 71% of people opting to fly with this airline when traveling to Jamaica. Keep in mind that there are 6 different airlines that fly to Jamaica on a routine basis, so you have a few additional options to choose from.

As of June 2026, there are 6 flights per week flying from Illinois to Jamaica. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.

Flight times from Illinois to Jamaica vary, but if you’re flying out of Chicago and flying into Montego Bay (one of the most popular routes), then the duration is 3h 55m on average. Another popular route from Illinois to Jamaica is flying from Moline to Montego Bay, which will take roughly 5h 48m. Keep in mind that layovers or delays could extend your travel time.