HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kingston

$186+ Cheap flights from Midway (MDW) to Kingston (KIN)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KIN
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Kingston with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Midway to Kingston

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Kingston (KIN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 20, 2025.

Round-trip from

$501
(Delta)

One-way from

$186
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$405
From Chicago Midway to Kingston Norman Manley
Search Deals
One-way flight from Chicago Midway to Kingston Norman Manley
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($129 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($45 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

Find flight deals from Midway to Kingston

Cheapest flights from Midway to Kingston
Explore the most affordable flight options available from Midway to Kingston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2025.

This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1512:43 pmMDW - KIN
1 stop7h 17mDelta
Mon 9/229:00 amKIN - MDW
1 stop12h 36mDelta
Deal found 8/17$501
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/49:35 amMDW - KIN
2 stops10h 25mDelta
Tue 10/79:00 amKIN - MDW
2 stops9h 25mDelta
Deal found 8/19$506
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/36:00 amMDW - KIN
1 stop14h 00mDelta
Fri 10/109:00 amKIN - MDW
1 stop13h 14mDelta
Deal found 8/19$697
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/276:00 amMDW - KIN
1 stop14h 25mDelta
Wed 9/39:25 amKIN - MDW
1 stop12h 01mDelta
Deal found 8/20$822
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/259:32 amMDW - KIN
2 stops25h 55mMultiple Airlines
Wed 9/36:25 pmKIN - MDW
1 stop14h 14mMultiple Airlines
Deal found 8/20$865
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/276:00 amMDW - KIN
1 stop14h 25mDelta
Tue 9/29:25 amKIN - MDW
1 stop12h 01mDelta
Deal found 8/20$941
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/279:30 amMDW - KIN
2 stops10h 55mDelta
Mon 9/19:25 amKIN - MDW
1 stop12h 01mDelta
Deal found 8/20$958
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/289:30 amMDW - KIN
2 stops10h 55mDelta
Tue 9/29:25 amKIN - MDW
2 stops9h 12mDelta
Deal found 8/18$1,014

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Kingston that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 20, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Kingston that are best for you.

Fly from

Midway

Fly to

Kingston

Route

Depart

Return

Price

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 9/15

12:43 pm-8:00 pm

1 stop7h 17m

Kingston Norman Manley

Mon 9/22

9:00 am-9:36 pm

1 stop12h 36m

$501

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 10/7

6:00 am-8:00 pm

1 stop14h 00m

Kingston Norman Manley

Sun 10/12

9:00 am-10:14 pm

1 stop13h 14m

$501

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 10/11

10:35 am-8:00 pm

1 stop9h 25m

Kingston Norman Manley

Sat 10/18

9:00 am-10:14 pm

1 stop13h 14m

$501

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 10/18

6:00 am-8:00 pm

1 stop14h 00m

Kingston Norman Manley

Wed 10/22

9:00 am-10:14 pm

1 stop13h 14m

$501

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 10/4

6:00 am-8:00 pm

1 stop14h 00m

Kingston Norman Manley

Tue 10/7

9:00 am-4:09 pm

1 stop7h 09m

$501

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 9/15

6:21 am-11:02 am

2 stops28h 41m

$186

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 9/17

6:00 am-8:00 pm

1 stop14h 00m

$212

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 9/15

10:35 am-8:00 pm

1 stop9h 25m

$212

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 9/17

9:00 am-11:02 am

3 stops26h 02m

$250

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 8/26

8:00 am-11:27 am

2 stops27h 27m

$365

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

Showing 1-10 of 11 results
1
2

Best time to book a flight from Midway to Kingston

Have a flexible travel schedule? Discover the best time to fly to Kingston from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Kingston

What is the cheapest month to book a flight from Chicago Midway Airport to Kingston?

Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Kingston (average of $425). Flying from Chicago Midway Airport to Kingston in December is currently the most expensive (average of $613). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Midway to Kingston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Kingston from Chicago Midway?

    If you book a flight to Kingston from Chicago Midway, you will be flying to Norman Manley, which is the city’s only airport. Kingston Norman Manley (KIN) is located 5.1 mi from the center of Kingston. There are 0 flights from Chicago Midway to Norman Manley per day from 0 different airlines.

  • How long is the flight from Chicago Midway Airport to Kingston?

    For as low as $501, Delta can have you in Kingston from Chicago Midway Airport in 7h 17m. Chicago Midway Airport and Kingston are separated by a distance of 1769 mi.

  • Can I find deals for flights from Midway to Kingston that include hotel bookings?

    Yes. In addition to deals on Midway to Kingston flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Kingston?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Kingston.

  • Can I find deals for business class flights from Midway to Kingston?

    Yes. Cheapflights offers flight deals from Midway to Kingston by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Kingston?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Kingston (average of $425). Flying from Chicago Midway Airport to Kingston in December is currently the most expensive (average of $613). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Kingston

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Montego Bay flights
Midway to Montego Bay flights
O'Hare Intl to Kingston flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.