Cheap flights from Jamaica to Chicago from $233

The month of December is, on average, the cheapest month to fly to Chicago from Jamaica, with most prices found around $367. If you’re not able to fly to Chicago in December, then May is your next best option. Flight prices from Jamaica to Chicago during May average around $377.

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $449. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Jamaica to Chicago for around $562.

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Jamaica to Chicago during this time can be as low as $477. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $486.

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

There are 2 cabin classes available to choose from on Jamaica to Chicago 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 Jamaica to Chicago.

The number of flights available between Jamaica and Chicago is 2 per day as of November 2026. The most frequent departure time is 2:00PM, with 100% of daily flights leaving in the afternoon.

The number of flights available between Jamaica and Chicago is 14 per week as of November 2026. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.