$197 Find Cheap Flights from Chicago Midway Airport to Jamaica - Compare and Save

The cheapest ticket to Jamaica from Chicago Midway Airport found in the last 5 days was to Montego Bay, at $663 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Montego Bay (MBJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was $663.

The cheapest time of day to fly to Jamaica is generally in the morning, when round-trip flights cost $580 on average. The most expensive time of day to fly to Jamaica is generally in the morning, which is peak travel time and where the average cost of a ticket is $580.

No, with an average price for the route of $467, prices are generally cheapest when you fly direct.

The cheapest month for flights from Chicago Midway Airport to Jamaica is December, when tickets cost $493 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $1,144 and $738 respectively.

There is just one airline that flies from Chicago Midway Airport to Jamaica direct and that is Southwest. The best round-trip deal found from Southwest for the route is to Montego Bay (MBJ) and costs $467.

In the past 5 days, the cheapest round-trip tickets from Chicago Midway Airport to Jamaica were found on Southwest ($442) and Delta ($495).

The duration of a flight to Jamaica depends on your arrival airport. The shortest routes to Jamaica from Chicago Midway Airport are to Montego Bay, which takes 3h 55m, and Kingston, which takes 5h 55m.

There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.