Cheap flights from Chicago to Jamaica from $205

The cheapest month to fly to Jamaica from Chicago is in April. Flight prices, which tend to average around $472, 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 $520.

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, Saturday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $643.

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

You are more likely to see cheaper flights to Jamaica from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Jamaica for around $569 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Jamaica from Chicago for as low as $479 on momondo.

There are 3 cabin classes available to choose from on Chicago 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 Chicago to Jamaica.

Frontier, Air Canada, and Southwest are the most popular carriers operating from Chicago to Jamaica

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Jamaica from Chicago according to our data. American Airlines is the first choice among our users, with 61% 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.

2 flights are operational daily from Chicago to Jamaica as of November 2026. The most popular departure time for this route is 8:00AM, with 100% of flights per day taking off at noon.

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