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$178+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KIN
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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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 septiembre 16, 2025.

Round-trip from

$433
(Delta)

One-way from

$178
(Delta)

Popular in

December

Cheapest in

February

Average price

$414
From Chicago Midway to Kingston Norman Manley
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One-way flight from Chicago Midway to Kingston Norman Manley
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Highest demand for flights based on searches. 20% potential increase in price ($136 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($44 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 septiembre 16, 2025.

This Delta deal was found by Cheapflights users on 9/14. 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.
dom. 10/1212:48 pmMDW - KIN
1 stop7h 12mDelta
dom. 10/199:00 amKIN - MDW
1 stop13h 14mDelta
Deal found 9/14$433
This Delta deal was found by Cheapflights users on 9/13. 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.
mié. 10/296:00 amMDW - KIN
1 stop14h 00mDelta
mié. 11/510:00 amKIN - MDW
2 stops9h 25mDelta
Deal found 9/13$438
This Delta deal was found by Cheapflights users on 9/16. 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.
lun. 9/2912:43 pmMDW - KIN
1 stop7h 17mDelta
jue. 10/29:00 amKIN - MDW
1 stop12h 36mDelta
Deal found 9/16$483
This Delta deal was found by Cheapflights users on 9/15. 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.
jue. 10/910:35 amMDW - KIN
1 stop9h 25mDelta
lun. 10/139:00 amKIN - MDW
1 stop7h 09mDelta
Deal found 9/15$517
This Delta deal was found by Cheapflights users on 9/15. 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.
vie. 10/176:00 amMDW - KIN
1 stop14h 00mDelta
mar. 10/219:00 amKIN - MDW
1 stop7h 09mDelta
Deal found 9/15$559
This Delta deal was found by Cheapflights users on 9/14. 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.
vie. 10/39:35 amMDW - KIN
2 stops10h 25mDelta
jue. 10/239:00 amKIN - MDW
1 stop13h 14mDelta
Deal found 9/14$564
This Delta deal was found by Cheapflights users on 9/16. 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.
vie. 10/316:00 amMDW - KIN
1 stop14h 00mDelta
vie. 11/710:00 amKIN - MDW
2 stops9h 25mDelta
Deal found 9/16$636

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 septiembre 16, 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

lun. 10/13

6:00 am-8:00 pm

1 stop14h 00m

Kingston Norman Manley

sáb. 10/18

9:00 am-10:14 pm

1 stop13h 14m

$433

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

dom. 10/12

12:48 pm-8:00 pm

1 stop7h 12m

Kingston Norman Manley

dom. 10/19

9:00 am-10:14 pm

1 stop13h 14m

$433

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

mié. 10/29

6:00 am-8:00 pm

1 stop14h 00m

Kingston Norman Manley

mié. 11/5

10:00 am-4:15 pm

1 stop7h 15m

$433

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

vie. 10/3

12:43 pm-8:00 pm

1 stop7h 17m

Kingston Norman Manley

jue. 10/23

9:00 am-10:14 pm

1 stop13h 14m

$438

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

lun. 9/29

6:00 am-8:00 pm

1 stop14h 00m

Kingston Norman Manley

jue. 10/2

9:00 am-6:35 pm

2 stops9h 35m

$488

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

jue. 10/9

10:35 am-8:00 pm

1 stop9h 25m

Kingston Norman Manley

lun. 10/13

9:00 am-10:14 pm

1 stop13h 14m

$517

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

mié. 10/22

10:35 am-8:00 pm

1 stop9h 25m

Kingston Norman Manley

dom. 10/26

9:00 am-10:14 pm

1 stop13h 14m

$559

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

vie. 10/31

6:00 am-8:00 pm

1 stop14h 00m

Kingston Norman Manley

vie. 11/7

10:00 am-10:14 pm

1 stop13h 14m

$559

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

lun. 10/13

6:00 am-8:00 pm

1 stop14h 00m

$178

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

lun. 10/13

4:24 pm-2:00 pm

2 stops21h 36m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 14 results
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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 $433, Delta can have you in Kingston from Chicago Midway Airport in 14h. 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

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