HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kingston

$188+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KIN
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
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 January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$466
(Delta)

One-way from

$188
(Delta)

Popular in

November

Cheapest in

February

Average price

$576
Provider with most accurate pricing for Chicago Midway-Kingston Norman Manley flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Kingston Norman Manley flights.
Search Deals
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. 21% potential increase in price ($154 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($41 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 15, 2026.

This Delta deal was found by Cheapflights users on 1/12. 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 2/276:00 am
MDW
-
KIN
1 stop13h 00m
Delta
Fri 3/69:00 am
KIN
-
MDW
1 stop14h 31m
Delta
Deal found 1/12$466
This Delta deal was found by Cheapflights users on 1/15. 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.
Thu 2/512:46 pm
MDW
-
KIN
1 stop6h 14m
Delta
Thu 2/129:00 am
KIN
-
MDW
1 stop14h 31m
Delta
Deal found 1/15$550
This Delta deal was found by Cheapflights users on 1/13. 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.
Tue 1/276:35 pm
MDW
-
KIN
2 stops24h 25m
Delta
Tue 2/109:00 am
KIN
-
MDW
2 stops24h 52m
Delta
Deal found 1/13$555
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/256:20 am
MDW
-
KIN
2 stops28h 52m
Multiple Airlines
Thu 2/53:30 pm
KIN
-
MDW
1 stop19h 40m
Multiple Airlines
Deal found 1/14$578
This Delta deal was found by Cheapflights users on 1/13. 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.
Thu 1/2212:48 pm
MDW
-
KIN
1 stop6h 12m
Delta
Fri 2/69:00 am
KIN
-
MDW
1 stop9h 29m
Delta
Deal found 1/13$594
This Kiwi.com deal was found by Cheapflights users on 1/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/186:30 pm
MDW
-
KIN
2 stops17h 45m
Multiple Airlines
Thu 1/293:30 pm
KIN
-
MDW
1 stop19h 40m
Multiple Airlines
Deal found 1/13$598
This Delta deal was found by Cheapflights users on 1/13. 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.
Sat 1/249:33 am
MDW
-
KIN
2 stops9h 27m
Delta
Sat 2/79:00 am
KIN
-
MDW
1 stop14h 22m
Delta
Deal found 1/13$599
This Kiwi.com deal was found by Cheapflights users on 1/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1011:05 am
MDW
-
KIN
1 stop27h 25m
Multiple Airlines
Tue 2/173:30 pm
KIN
-
MDW
1 stop19h 40m
Multiple Airlines
Deal found 1/13$627
This Kiwi.com deal was found by Cheapflights users on 1/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/186:30 pm
MDW
-
KIN
2 stops17h 45m
Multiple Airlines
Sun 2/13:30 pm
KIN
-
MDW
1 stop19h 40m
Multiple Airlines
Deal found 1/13$633
This Delta deal was found by Cheapflights users on 1/14. 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.
Mon 6/296:00 am
MDW
-
KIN
1 stop14h 00m
Delta
Sat 7/49:00 am
KIN
-
MDW
1 stop12h 45m
Delta
Deal found 1/14$634
This Delta deal was found by Cheapflights users on 1/13. 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.
Tue 1/276:35 pm
MDW
-
KIN
2 stops24h 25m
Delta
Fri 1/309:00 am
KIN
-
MDW
1 stop9h 29m
Delta
Deal found 1/13$639
This Delta deal was found by Cheapflights users on 1/13. 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.
Fri 2/206:00 am
MDW
-
KIN
1 stop13h 00m
Delta
Mon 2/239:00 am
KIN
-
MDW
1 stop9h 45m
Delta
Deal found 1/13$659

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 January 15, 2026.
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

Fri 2/27

6:00 am-8:00 pm

1 stop13h 00m

Kingston Norman Manley

Fri 3/6

9:00 am-10:31 pm

1 stop14h 31m

$466

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 4/7

10:45 am-8:00 pm

1 stop9h 15m

Kingston Norman Manley

Sat 4/18

9:00 am-10:29 pm

1 stop13h 29m

$466

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 3/11

6:25 am-8:00 pm

1 stop13h 35m

Kingston Norman Manley

Sun 3/15

9:00 am-10:31 pm

1 stop13h 31m

$550

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 3/27

12:47 pm-8:00 pm

1 stop7h 13m

Kingston Norman Manley

Mon 4/6

9:00 am-4:55 pm

1 stop7h 55m

$550

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 1/30

12:48 pm-8:00 pm

1 stop6h 12m

Kingston Norman Manley

Sat 2/14

9:00 am-3:21 pm

1 stop7h 21m

$550

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 2/5

10:48 am-8:00 pm

1 stop8h 12m

Kingston Norman Manley

Thu 2/12

9:00 am-10:31 pm

1 stop14h 31m

$550

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 1/27

6:35 pm-8:00 pm

2 stops24h 25m

Kingston Norman Manley

Fri 2/6

9:00 am-10:22 pm

1 stop14h 22m

$555

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sun 1/25

10:48 am-8:00 pm

1 stop8h 12m

Kingston Norman Manley

Thu 2/5

9:00 am-10:22 pm

1 stop14h 22m

$594

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 1/21

12:48 pm-8:00 pm

1 stop6h 12m

Kingston Norman Manley

Sat 2/7

9:00 am-3:38 pm

1 stop7h 38m

$594

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 2/27

6:00 am-8:00 pm

1 stop13h 00m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/13

Showing 1-10 of 14 results
1
2

Compare providers for flights from Midway to Kingston

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Kingston in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Kingston flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Kingston flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Kingston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Kingston flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Kingston flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Kingston (average of $384). Flying from Chicago Midway Airport to Kingston in March is currently the most expensive (average of $595). 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 $466, Delta can have you in Kingston from Chicago Midway Airport in 13h. 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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Kingston (average of $384). Flying from Chicago Midway Airport to Kingston in March is currently the most expensive (average of $595). 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

Traveling to a place near Kingston?

Book flights to Kingston if you plan to visit one of these locations
Port Antonio

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.