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$165+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KIN
Jan 1 — Jan 81
Thu 1/1
Thu 1/8
1 adult, Economy
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Cheap 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 December 2, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
Thu 12/256:12 amMDW - KIN
2 stops29h 02mMultiple Airlines
Sun 12/283:30 pmKIN - MDW
1 stop19h 35mMultiple Airlines
Deal found 12/1$633
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
Fri 12/264:15 pmMDW - KIN
1 stop21h 15mMultiple Airlines
Mon 1/121:17 pmKIN - MDW
2 stops22h 17mMultiple Airlines
Deal found 12/1$695
This Delta deal was found by Cheapflights users on 11/30. 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 12/306:00 amMDW - KIN
1 stop12h 56mDelta
Tue 1/69:00 amKIN - MDW
1 stop8h 29mDelta
Deal found 11/30$827
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 12/294:15 pmMDW - KIN
1 stop21h 15mMultiple Airlines
Mon 1/58:10 pmKIN - MDW
2 stops42h 56mMultiple Airlines
Deal found 12/1$933
This Delta deal was found by Cheapflights users on 12/1. 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 12/910:49 amMDW - KIN
1 stop8h 17mDelta
Thu 12/119:00 amKIN - MDW
1 stop8h 18mDelta
Deal found 12/1$954

Find 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 December 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$445
(Delta)

One-way from

$165
(Kiwi.com)

Popular in

November

Cheapest in

February

Average price

$771
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. 23% potential increase in price ($175 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 2, 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

Fri 1/23

10:48 am-8:00 pm

1 stop8h 12m

Kingston Norman Manley

Sat 1/31

9:00 am-3:38 pm

1 stop7h 38m

$445

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sun 1/18

6:45 am-8:00 pm

1 stop12h 15m

Kingston Norman Manley

Fri 1/23

9:00 am-10:22 pm

1 stop14h 22m

$529

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 12/26

4:15 pm-2:30 pm

1 stop21h 15m

Kingston Norman Manley

Mon 1/12

1:17 pm-10:34 am

2 stops22h 17m

$695

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 12/25

6:12 am-12:14 pm

2 stops29h 02m

Kingston Norman Manley

Sat 12/27

3:15 am-3:20 pm

1 stop13h 05m

$754

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 12/30

6:00 am-7:56 pm

1 stop12h 56m

Kingston Norman Manley

Tue 1/6

9:00 am-4:29 pm

1 stop8h 29m

$827

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 12/29

4:15 pm-2:30 pm

1 stop21h 15m

Kingston Norman Manley

Mon 1/5

8:10 pm-2:06 pm

2 stops42h 56m

$933

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 12/9

10:49 am-8:06 pm

1 stop8h 17m

Kingston Norman Manley

Thu 12/11

9:00 am-4:18 pm

1 stop8h 18m

$954

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 1/29

6:20 am-12:12 pm

2 stops28h 52m

$165

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 1/29

6:00 am-8:00 pm

1 stop13h 00m

$178

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sat 12/27

8:15 am-12:14 pm

2 stops26h 59m

$312

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/29

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 December.
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 $594). 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 $445, Delta can have you in Kingston from Chicago Midway Airport in 8h 12m. 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 $594). 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?

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Port Antonio

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