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$171+ 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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KIN
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
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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 October 23, 2025.

This Delta deal was found by Cheapflights users on 10/21. 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 12/56:00 amMDW - KIN
1 stop13h 06mDelta
Fri 12/129:00 amKIN - MDW
1 stop8h 18mDelta
Deal found 10/21$562
This Richmond deal was found by Cheapflights users on 10/23. 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 Richmond is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:00 amMDW - KIN
1 stop13h 00mDelta
Fri 11/289:00 amKIN - MDW
1 stop15h 40mDelta
Deal found 10/23$581
This Delta deal was found by Cheapflights users on 10/20. 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.
Mon 10/2710:35 amMDW - KIN
1 stop9h 25mDelta
Fri 10/319:00 amKIN - MDW
1 stop13h 14mDelta
Deal found 10/20$690
This Mytrip deal was found by Cheapflights users on 10/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/51:50 pmMDW - KIN
2 stops23h 40mMultiple Airlines
Fri 12/124:30 pmKIN - MDW
3 stops21h 38mMultiple Airlines
Deal found 10/21$981

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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$562
(Delta)

One-way from

$171
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$565
Provider with most accurate pricing for Chicago Midway-Kingston Norman Manley flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Kingston Norman Manley flights.
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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. 14% potential increase in price ($93 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 October 23, 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 12/5

6:00 am-8:06 pm

1 stop13h 06m

Kingston Norman Manley

Fri 12/12

9:00 am-4:18 pm

1 stop8h 18m

$562

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 11/24

6:00 am-8:00 pm

1 stop13h 00m

Kingston Norman Manley

Fri 11/28

9:00 am-11:40 pm

1 stop15h 40m

$581

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 10/27

10:35 am-8:00 pm

1 stop9h 25m

Kingston Norman Manley

Fri 10/31

9:00 am-10:14 pm

1 stop13h 14m

$690

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 12/5

1:50 pm-2:30 pm

2 stops23h 40m

Kingston Norman Manley

Fri 12/12

4:30 pm-1:08 pm

3 stops21h 38m

$981

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 11/4

1:56 pm-12:01 pm

2 stops21h 05m

$171

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 11/6

1:37 pm-12:01 pm

2 stops21h 24m

$208

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Wed 11/5

6:00 am-9:00 pm

1 stop14h 00m

$262

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Tue 11/4

10:40 am-9:00 pm

1 stop9h 20m

$306

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Mon 11/3

10:30 am-9:00 pm

1 stop9h 30m

$306

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Thu 11/6

10:40 am-9:00 pm

1 stop9h 20m

$306

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/22

Showing 1-10 of 13 results
1
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Kingston flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 $562, Delta can have you in Kingston from Chicago Midway Airport in 13h 06m. 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

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