$233+ 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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KIN
Sep 6 — Sep 131
Round-trip
1 adult, Economy
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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
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 August 7, 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 August 7, 2026.
This Delta deal was found by Cheapflights users on 8/5. 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.
Sat 9/196:05 am -
1 stop14h 05m
Sat 9/269:10 am -
1 stop13h 34m
Deal found 8/5![Delta logo]()
$556
This Delta deal was found by Cheapflights users on 8/5. 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 9/210:54 am -
1 stop9h 19m
Wed 9/99:10 am -
1 stop13h 34m
Deal found 8/5![Delta logo]()
$675
This Delta deal was found by Cheapflights users on 8/5. 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 10/79:29 am -
2 stops10h 46m
Sat 10/179:15 am -
2 stops8h 45m
Deal found 8/5![Delta logo]()
$680
This Delta deal was found by Cheapflights users on 8/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:05 am -
1 stop14h 08m
Sat 8/229:13 am -
1 stop13h 23m
Deal found 8/4![Delta logo]()
$698
This Delta deal was found by Cheapflights users on 8/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1311:28 am -
1 stop6h 32m
Thu 1/219:00 am -
1 stop14h 10m
Deal found 8/4![Delta logo]()
$765
This Delta deal was found by Cheapflights users on 8/7. 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.
Thu 10/19:29 am -
2 stops10h 41m
Sat 10/109:15 am -
2 stops8h 45m
Deal found 8/7![Delta logo]()
$795
This Delta deal was found by Cheapflights users on 8/6. 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 8/216:05 am -
1 stop14h 08m
Sun 8/309:13 am -
1 stop13h 23m
Deal found 8/6![Delta logo]()
$804
This Delta deal was found by Cheapflights users on 8/6. 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 8/229:24 am -
2 stops10h 49m
Sat 8/299:13 am -
1 stop13h 23m
Deal found 8/6![Delta logo]()
$809
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 August 7, 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 August 7, 2026.
This Delta deal was found by Cheapflights users on 8/2. 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 10/36:05 am -
1 stop14h 05m
Sat 10/109:15 am -
1 stop13h 18m
Deal found 8/2![Delta logo]()
$556
This Delta deal was found by Cheapflights users on 8/3. 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.
Fri 9/256:05 am -
1 stop14h 05m
Mon 9/289:10 am -
1 stop7h 05m
Deal found 8/3![Delta logo]()
$556
This Delta deal was found by Cheapflights users on 8/2. 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 9/1610:48 am -
1 stop9h 22m
Wed 9/239:10 am -
1 stop7h 05m
Deal found 8/2![Delta logo]()
$556
This Delta deal was found by Cheapflights users on 8/5. 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.
Sat 9/199:29 am -
2 stops10h 41m
Sat 9/269:10 am -
2 stops9h 12m
Deal found 8/5![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 8/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:29 am -
2 stops10h 41m
Mon 9/219:10 am -
1 stop13h 34m
Deal found 8/4![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 8/4. 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 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 -
2 stops8h 45m
Deal found 8/4![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 8/6. 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 8/229:24 am -
2 stops10h 49m
Fri 8/289:13 am -
2 stops24h 04m
Deal found 8/6![Delta logo]()
$809
This Delta deal was found by Cheapflights users on 8/5. 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 8/216:05 am -
1 stop14h 08m
Sun 8/239:13 am -
1 stop13h 23m
Deal found 8/5![Delta logo]()
$832
Last-minute flights from Midway to KingstonDiscover last-minute flight deals from Midway to Kingston. Data last updated August 7, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Kingston. Data last updated August 7, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:05 am -
1 stop14h 08m
Sat 8/229:13 am -
1 stop13h 23m
Deal found 8/4![Delta logo]()
$698
This Delta deal was found by Cheapflights users on 8/6. 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 8/216:05 am -
1 stop14h 08m
Sun 8/309:13 am -
1 stop13h 23m
Deal found 8/6![Delta logo]()
$804
This Delta deal was found by Cheapflights users on 8/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:05 am -
1 stop14h 08m
Sun 8/239:13 am -
1 stop13h 23m
Deal found 8/4![Delta logo]()
$832
This Delta deal was found by Cheapflights users on 8/6. 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 8/229:24 am -
2 stops10h 49m
Sat 8/299:13 am -
1 stop13h 23m
Deal found 8/6![Delta logo]()
$809
This Delta deal was found by Cheapflights users on 8/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:05 am -
1 stop14h 08m
Wed 9/29:13 am -
1 stop13h 23m
Deal found 8/4![Delta logo]()
$694
This Delta deal was found by Cheapflights users on 8/5. 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 9/210:54 am -
1 stop9h 19m
Wed 9/99:10 am -
1 stop13h 34m
Deal found 8/5![Delta logo]()
$675
This Delta deal was found by Cheapflights users on 8/5. 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.
Sat 9/196:05 am -
1 stop14h 05m
Sat 9/269:10 am -
1 stop13h 34m
Deal found 8/5![Delta logo]()
$556
This Delta deal was found by Cheapflights users on 8/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:29 am -
2 stops10h 41m
Mon 9/219:10 am -
1 stop13h 34m
Deal found 8/4![Delta logo]()
$561
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 August 7, 2026.
Search for one-way flight options from Midway to Kingston. Find affordable one-way fares based on user searches. Data last updated August 7, 2026.
This Delta deal was found by Cheapflights users on 8/5. 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.
Sat 9/196:05 am -
1 stop14h 05m
Deal found 8/5![Delta logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1412:54 pm -
3 stops43h 16m
Deal found 8/3![Multiple Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 8/7. 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 8/2210:56 am -
1 stop9h 17m
Deal found 8/7![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 8/7. 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.
Fri 8/216:42 pm -
2 stops25h 31m
Deal found 8/7![Delta logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Wed 9/26:05 am -
3 stops12h 40m
Deal found 8/5![Multiple Airlines logo]()
$406
This Delta deal was found by Cheapflights users on 8/7. 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 9/210:54 am -
1 stop9h 19m
Deal found 8/7![Delta logo]()
$427
This Delta deal was found by Cheapflights users on 8/3. 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.
Mon 9/149:24 am -
2 stops10h 46m
Deal found 8/3![Delta logo]()
$442
This Delta deal was found by Cheapflights users on 8/6. 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 9/109:29 am -
2 stops10h 41m
Deal found 8/6![Delta logo]()
$445
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:25 am -
3 stops25h 45m
Deal found 8/3![Multiple Airlines logo]()
$465
This Delta deal was found by Cheapflights users on 8/7. 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.
Thu 9/36:05 am -
1 stop14h 08m
Deal found 8/7![Delta logo]()
$476
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Mon 8/1011:06 am -
3 stops26h 04m
Deal found 8/5![Multiple Airlines logo]()
$510
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 August 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $556 (Delta) |
One-way from | $233 (Delta) |
Popular in | November |
Cheapest in | October |
Average price | $513 |
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 August 7, 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
Sat 10/3
6:05 am-8:10 pm
1 stop14h 05m
Kingston Norman Manley
Sat 10/10
9:15 am-10:33 pm
1 stop13h 18m
$556
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Fri 9/25
6:05 am-8:10 pm
1 stop14h 05m
Kingston Norman Manley
Mon 9/28
9:10 am-4:15 pm
1 stop7h 05m
$556
Quickest round-trip
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Wed 9/16
10:48 am-8:10 pm
1 stop9h 22m
Kingston Norman Manley
Wed 9/23
9:10 am-4:15 pm
1 stop7h 05m
$556
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Sat 9/19
9:29 am-8:10 pm
2 stops10h 41m
Kingston Norman Manley
Sat 9/26
9:10 am-6:22 pm
2 stops9h 12m
$561
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Sat 9/19
9:29 am-8:10 pm
2 stops10h 41m
Kingston Norman Manley
Mon 9/21
9:10 am-10:44 pm
1 stop13h 34m
$561
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Wed 10/7
6:04 am-8:15 pm
1 stop14h 11m
Kingston Norman Manley
Sat 10/17
9:15 am-6:00 pm
2 stops8h 45m
$561
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Sat 8/22
9:24 am-8:13 pm
2 stops10h 49m
Kingston Norman Manley
Fri 8/28
9:13 am-9:17 am
2 stops24h 04m
$809
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Fri 8/21
6:05 am-8:13 pm
1 stop14h 08m
Kingston Norman Manley
Sun 8/23
9:13 am-10:36 pm
1 stop13h 23m
$832
Cheapest one-way
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Sat 9/19
6:05 am-8:10 pm
1 stop14h 05m
$233
ChicagoKingston
MDW Chicago Midway - KIN Kingston Norman Manley
MDWKIN
Chicago Midway
Sun 9/13
6:05 am-8:10 pm
1 stop14h 05m
$233
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 August.
| 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 August 7, 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.
Crew
8.5
Food
7.2
Comfort
7.8
Overall
7.8
Entertainment
7.8
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Food
7.2
Comfort
7.8
Overall
7.8
Entertainment
7.8
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
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
Explore flights to Kingston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 7, 2026.
Midway and Kingston flights
Browse other Midway and Kingston flight options. Last updated on August 7, 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 August 7, 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 2,558,603 searches. Data last updated August 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$445 | Average$636 | FlexibilityNo cancel fee | On-timeN/A |