Cheap flights from Illinois to Jamaica from $147

The cheapest month to fly to Jamaica from Illinois is in April. Flight prices, which tend to average around $482, 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 April, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $496.

The cheapest day to depart on your flight to Jamaica is on a Tuesday when prices can be found for as low as $488. 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 $596.

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 $526 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 $463 on momondo.

There are 4 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.

No. A direct flight is the cheapest option for a flight between Illinois to Jamaica.

Air Canada, United Airlines, and Frontier are the most popular carriers operating from Illinois to Jamaica

American Airlines, United Airlines and Delta 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 68% 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 August 2026, 1 flights take off from Illinois and land in Jamaica each day. The most common flight departure time for this route is 9:00AM, with 100% of daily flights taking off at noon.

As of August 2026, there are 7 flights per week flying from Illinois to Jamaica. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.