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$212+ 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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KIN
Jul 16 — Jul 231
Wed 7/16
Wed 7/23
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 July 11, 2025.

Round-trip from

$381
(Delta)

One-way from

$212
(Delta)

Popular in

December

Cheapest in

February

Average price

$696
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. 14% potential increase in price ($102 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($42 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 11, 2025.

This Delta deal was found by Cheapflights users on 7/9. 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 10/810:35 amMDW - KIN
1 stop9h 25mDelta
Wed 10/159:00 amKIN - MDW
1 stop12h 44mDelta
Deal found 7/9$381
This Mytrip deal was found by Cheapflights users on 7/9. 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 7/2510:31 amMDW - KIN
2 stops21h 16mMultiple Airlines
Sun 7/2712:05 pmKIN - MDW
2 stops21h 36mMultiple Airlines
Deal found 7/9$516

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 July 11, 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

Wed 10/8

10:35 am-8:00 pm

1 stop9h 25m

Kingston Norman Manley

Wed 10/15

9:00 am-9:44 pm

1 stop12h 44m

$381

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 7/25

10:31 am-7:47 am

2 stops21h 16m

Kingston Norman Manley

Sun 7/27

12:05 pm-9:41 am

2 stops21h 36m

$516

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 8/22

10:31 am-8:25 pm

1 stop9h 54m

$212

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Fri 12/12

5:35 pm-8:35 pm

3 stops26h 00m

$351

ChicagoKingston

MDW - KIN

MDWKIN

Chicago Midway

Sun 12/28

12:10 pm-3:41 pm

2 stops50h 31m

$1,581

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/8

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.

Reviews of airlines servicing Kingston

Get insights into the airlines that provide service to Kingston. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kingston. Reviews last updated July 11, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Kingston, such as Delta and WestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,951 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,951 reviews
Delta
8.0
Very good
7,951 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,924 reviews
Delta
8.0
Very good
7,951 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What is the cheapest airline to fly from Chicago Midway Airport to Kingston round-trip?

    Delta, at $381, was found to be the cheapest airline from Chicago Midway Airport to Kingston..

  • 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Port Antonio

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