$210 Find Cheap Flights from Jamaica to Chicago Midway Airport

Based on KAYAK data, the cheapest day to fly to Chicago is Saturday where round-trip tickets can be as cheap as $473. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $473 on average.

The cheapest time of day to fly to Chicago Midway Airport is generally in the afternoon, when round-trip flights cost $473 on average. The most expensive time of day to fly to Chicago Midway Airport is generally in the evening, which is peak travel time and where the average cost of a ticket is $763.

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously, any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from Montego Bay, which takes 4h 26m, and Kingston, which takes 8h 46m.

There are around 281 direct flights from within Jamaica to Chicago Midway Airport every day. Most flights depart in the morning, with 40% of flights departing in the morning.

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago Midway Airport. Instead, there are 2 medium-haul flights (3-6 hour flight duration), with the most arriving from Montego Bay.

From Jamaica, there are direct flights to Chicago Midway Airport from 1 city. This city is Montego Bay and there are 2 direct flights each week.