$369+ Cheap flights from Midway (MDW) to Kingston (KIN)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KIN
Nov 7 — Nov 141
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Kingston with Cheapflights
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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
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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
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to KingstonExplore 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 8, 2026.
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 8, 2026.
This Delta deal was found by Cheapflights users on 10/3. 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 12/86:00 am -
1 stop13h 00m
Mon 12/219:00 am -
1 stop8h 19m
Deal found 10/3![Delta logo]()
$854
This Delta deal was found by Cheapflights users on 10/5. 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 11/46:04 am -
1 stop13h 11m
Wed 11/119:00 am -
2 stops10h 04m
Deal found 10/5![Delta logo]()
$859
This Mytrip deal was found by Cheapflights users on 10/4. 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 11/66:42 pm -
3 stops23h 58m
Mon 11/92:00 pm -
3 stops28h 47m
Deal found 10/4![Multiple Airlines logo]()
$894
This Delta deal was found by Cheapflights users on 10/3. 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 12/126:00 am -
1 stop13h 00m
Tue 12/159:00 am -
1 stop8h 16m
Deal found 10/3![Delta logo]()
$898
This Delta deal was found by Cheapflights users on 10/5. 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 10/76:04 am -
1 stop14h 11m
Sat 10/179:15 am -
1 stop13h 18m
Deal found 10/5![Delta logo]()
$917
This Mytrip deal was found by Cheapflights users on 10/5. 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.
Thu 11/1912:20 pm -
3 stops29h 25m
Thu 11/269:10 am -
3 stops24h 02m
Deal found 10/5![Multiple Airlines logo]()
$939
This Mytrip deal was found by Cheapflights users on 10/6. 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 10/236:15 am -
3 stops25h 55m
Fri 10/309:10 am -
3 stops32h 37m
Deal found 10/6![Multiple Airlines logo]()
$940
Best flights from Midway to KingstonDiscover carefully curated flight deals from Midway to Kingston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 8, 2026.
Discover carefully curated flight deals from Midway to Kingston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 8, 2026.
This Delta deal was found by Cheapflights users on 10/5. 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 11/46:04 am -
1 stop13h 11m
Wed 11/119:00 am -
1 stop8h 18m
Deal found 10/5![Delta logo]()
$854
This Delta deal was found by Cheapflights users on 10/5. 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 11/196:00 am -
1 stop13h 00m
Thu 11/269:00 am -
1 stop7h 15m
Deal found 10/5![Delta logo]()
$854
This Delta deal was found by Cheapflights users on 10/3. 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 12/86:00 am -
1 stop13h 00m
Sun 12/209:00 am -
1 stop8h 19m
Deal found 10/3![Delta logo]()
$854
This Delta deal was found by Cheapflights users on 10/3. 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 12/126:00 am -
1 stop13h 00m
Tue 12/159:00 am -
1 stop8h 16m
Deal found 10/3![Delta logo]()
$898
This Delta deal was found by Cheapflights users on 10/6. 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 3/189:30 am -
2 stops10h 30m
Thu 3/259:00 am -
1 stop7h 25m
Deal found 10/6![Delta logo]()
$920
This Delta deal was found by Cheapflights users on 10/6. 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 3/209:30 am -
2 stops10h 30m
Sat 3/279:00 am -
2 stops9h 37m
Deal found 10/6![Delta logo]()
$920
This Delta deal was found by Cheapflights users on 10/6. 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 10/2310:59 am -
1 stop9h 16m
Fri 10/309:15 am -
1 stop13h 18m
Deal found 10/6![Delta logo]()
$948
This Delta deal was found by Cheapflights users on 10/3. 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 12/126:00 am -
1 stop13h 00m
Fri 12/189:00 am -
1 stop14h 54m
Deal found 10/3![Delta logo]()
$961
This Delta deal was found by Cheapflights users on 10/5. 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 3/2610:35 am -
1 stop9h 25m
Fri 4/29:00 am -
1 stop13h 10m
Deal found 10/5![Delta logo]()
$1,098
Last-minute flights from Midway to KingstonDiscover last-minute flight deals from Midway to Kingston. Data last updated October 8, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Kingston. Data last updated October 8, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/5. 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 10/76:04 am -
1 stop14h 11m
Sat 10/179:15 am -
1 stop13h 18m
Deal found 10/5![Delta logo]()
$917
This Delta deal was found by Cheapflights users on 10/7. 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 10/1011:33 am -
1 stop8h 42m
Sat 10/179:15 am -
1 stop13h 18m
Deal found 10/7![Delta logo]()
$968
This Mytrip deal was found by Cheapflights users on 10/6. 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 10/236:15 am -
3 stops25h 55m
Fri 10/309:10 am -
3 stops32h 37m
Deal found 10/6![Multiple Airlines logo]()
$940
This Delta deal was found by Cheapflights users on 10/5. 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 11/46:04 am -
1 stop13h 11m
Wed 11/119:00 am -
1 stop8h 18m
Deal found 10/5![Delta logo]()
$854
This Mytrip deal was found by Cheapflights users on 10/4. 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 11/66:42 pm -
3 stops23h 58m
Mon 11/92:00 pm -
3 stops28h 47m
Deal found 10/4![Multiple Airlines logo]()
$894
This Mytrip deal was found by Cheapflights users on 10/5. 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.
Thu 11/1912:20 pm -
3 stops29h 25m
Thu 11/269:10 am -
3 stops24h 02m
Deal found 10/5![Multiple Airlines logo]()
$939
One-way flights from Midway to KingstonSearch for one-way flight options from Midway to Kingston. Find affordable one-way fares based on user searches. Data last updated October 8, 2026.
Search for one-way flight options from Midway to Kingston. Find affordable one-way fares based on user searches. Data last updated October 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 11/56:42 pm -
3 stops36h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 10/5. 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 11/411:39 am -
1 stop7h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Delta logo]()
$382
This Delta deal was found by Cheapflights users on 10/7. 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 11/111:05 pm -
1 stop5h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Delta logo]()
$392
This Kiwi.com deal was found by Cheapflights users on 10/7. 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.
Wed 12/239:23 pm -
3 stops44h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$496
This Delta deal was found by Cheapflights users on 10/5. 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 11/59:29 am -
2 stops9h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Delta logo]()
$610
This Kiwi.com deal was found by Cheapflights users on 10/6. 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.
Wed 12/166:41 pm -
3 stops45h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$897
This Delta deal was found by Cheapflights users on 10/6. 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 12/1611:28 am -
1 stop7h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Delta logo]()
$1,170
This Delta deal was found by Cheapflights users on 10/7. 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 12/2312:55 pm -
1 stop6h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Delta logo]()
$1,180
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 October 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $854 (Delta) |
One-way from | $369 (Kiwi.com) |
Popular in | February |
Cheapest in | September |
Average price | $542 |
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 7,457,451 searches. Data last updated October 8, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Kingston that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Thu 11/5
6:42 pm-8:10 am
3 stops36h 28m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$369
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Wed 11/4
11:39 am-8:15 pm
1 stop7h 36m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$382
Quickest round-trip
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Wed 11/11
1:05 pm-8:00 pm
1 stop5h 55m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$392
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Wed 12/23
9:23 pm-6:45 pm
3 stops44h 22m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$496
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Thu 11/5
9:29 am-8:15 pm
2 stops9h 46m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$610
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Wed 11/4
6:04 am-8:15 pm
1 stop13h 11m
Kingston Norman Manley
Wed 11/11
9:00 am-4:18 pm
1 stop8h 18m
$854
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Thu 11/19
6:00 am-8:00 pm
1 stop13h 00m
Kingston Norman Manley
Thu 11/26
9:00 am-3:15 pm
1 stop7h 15m
$854
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Tue 12/8
6:00 am-8:00 pm
1 stop13h 00m
Kingston Norman Manley
Sun 12/20
9:00 am-4:19 pm
1 stop8h 19m
$854
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Sat 12/12
6:00 am-8:00 pm
1 stop13h 00m
Kingston Norman Manley
Tue 12/15
9:00 am-4:16 pm
1 stop8h 16m
$898
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Thu 3/18
9:30 am-8:00 pm
2 stops10h 30m
Kingston Norman Manley
Thu 3/25
9:00 am-4:25 pm
1 stop7h 25m
$920
Showing 1-10 of 18 resultsSorted by cheapest first
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.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
MDW-KIN
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.
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 October 8, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Kingston, such as Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.8
Boarding
8.1
Crew
8.5
Overall
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Entertainment
7.8
Boarding
8.1
Crew
8.5
Overall
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
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.
Traveling to a place near Kingston?
Book flights to Kingston if you plan to visit one of these locationsPort Antonio
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Other flights to Kingston
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Midway and Kingston flights
Browse other Midway and Kingston flight options. Last updated on October 8, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on October 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Midway to Kingston
Discover the top airline that operate flights from Midway to Kingston. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$445 | Average$638 | FlexibilityNo cancel fee | On-timeN/A |