The cheapest times to fly from MDW to KIN are

  • January 8th to March 4th
  • April 23rd to June 3rd (except the week of May 7th)
  • September 3rd to December 9th (except the week of November 19th)

based on data collected exclusively by Champion Traveler across tens of millions of flights. Among all the dates above, the very cheapest time to fly from MDW to KIN is mid November. Prices can be as high as $1659 for Sunday flights during mid December, or as low as $445 for Tuesday flights around mid November.


When to Fly to Kingston

Flying from Chicago, IL (MDW) to Kingston (KIN) will usually cost between $450 to $806 per person if booking more than four weeks in advance. On average the very cheapest time to fly is mid November with an average ticket price of $451. Due to high demand the most expensive time to fly is mid December, with an average price of $1170. Planning your trip to low-cost times can easily save you $719 on economy flights and even more on first-class flights. Generally, any price below $499 can be considered a good price for a round-trip MDW to KIN flight.

See below for a graph of average weekly prices for the MDW to KIN route. All prices are for round-trip tickets in USD.

MDW to KIN Flight Prices

Compared to other flights, the MDW to KIN flight is much cheaper than the average and costs less than the average flight leaving from Chicago. The average price per mile (for a direct flight) is $0.18, which is below average.


Flight Prices by Day of the Week

Tuesday is usually the cheapest day to fly to KIN, and Wednesday the cheapest day to fly back into MDW. Sundays are the most expensive days to fly to Kingston, and Saturdays are the most expensive days to return to Chicago. Selecting flights on the least expensive days could save you up to $122 (19%) on this flight.

Departing prices are for round-trip flights returning on the day of departure. For example, a flight departing on Tuesday and returning a week later will cost an average of $510. Return trip prices are from the KIN to MDW flight, and often highlight the quality of our data in showing the same trend.

Departing Prices by Day

Departure Day Prices

Return Trip Prices by Day

Return Day Prices


Nonstop Flights and Layovers

Travelers looking to fly from MDW to KIN can generally find a 1-layover flight. Because there is not usually a direct flight option the real-world direct flight time of 4 hour 10 minutes may not be realistic.


Flight Questions Answered

Still have questions about flying from MDW to KIN? We’ve got answers.

Which airlines fly this route?

You can find 2 major airlines flying this route most often: Cayman Airways, Delta, and potentially more during busy seasons.

How far away is it from Norman Manley International Airport to Chicago Midway International Airport?

The distance between the two airports is roughly 1770 miles or 2849 kilometers.

How long does it take to fly from MDW to KIN?

The real-world flight time for a nonstop MDW to KIN flight is about 4 hour 10 minutes.

How many flights go between Chicago, IL and Kingston?

It depends on the day of the week and the date, but a typical day might have around 33 available flights from MDW to KIN.


Airport Location Info


Departing Airport

Origination codeMDW
Origination airport nameChicago Midway International Airport
CityChicago, IL
Countrythe United States

Return Airport

Destination codeKIN
Destination airport nameNorman Manley International Airport


Other Resources

Please note that while we’ve worked hard to analyzed tens of millions of flights to get you this data, we do not calculate current live prices or guarantee pricing. Please see our partners using the links above for current offers.