$227+ 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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KIN
Aug 22 — Aug 291
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 July 23, 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 July 23, 2026.
This Delta deal was found by Cheapflights users on 7/21. 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 8/216:05 am
MDW
- KIN
1 stop14h 08m
Delta
Sun 8/239:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 7/21![Delta logo]()
$544
This Delta deal was found by Cheapflights users on 7/22. 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 9/1011:35 am
MDW
- KIN
1 stop8h 35m
Delta
Sat 9/129:10 am
KIN
- MDW
1 stop13h 34m
Delta
Deal found 7/22![Delta logo]()
$584
This Delta deal was found by Cheapflights users on 7/21. 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 9/410:54 am
MDW
- KIN
1 stop9h 19m
Delta
Fri 9/119:10 am
KIN
- MDW
1 stop13h 34m
Delta
Deal found 7/21![Delta logo]()
$590
This Delta deal was found by Cheapflights users on 7/18. 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 8/189:24 am
MDW
- KIN
2 stops10h 49m
Delta
Tue 8/259:13 am
KIN
- MDW
2 stops9h 20m
Delta
Deal found 7/18![Delta logo]()
$595
This Delta deal was found by Cheapflights users on 7/22. 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 9/46:05 am
MDW
- KIN
1 stop14h 08m
Delta
Sun 9/139:10 am
KIN
- MDW
1 stop13h 34m
Delta
Deal found 7/22![Delta logo]()
$630
This Delta deal was found by Cheapflights users on 7/19. 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
MDW
- KIN
1 stop9h 19m
Delta
Wed 9/99:10 am
KIN
- MDW
1 stop13h 34m
Delta
Deal found 7/19![Delta logo]()
$669
This Delta deal was found by Cheapflights users on 7/19. 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 10/3111:35 am
MDW
- KIN
1 stop7h 55m
Delta
Mon 11/99:00 am
KIN
- MDW
1 stop14h 10m
Delta
Deal found 7/19![Delta logo]()
$678
This Delta deal was found by Cheapflights users on 7/17. 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 10/71:00 pm
MDW
- KIN
1 stop6h 30m
Delta
Sat 10/179:00 am
KIN
- MDW
1 stop13h 25m
Delta
Deal found 7/17![Delta logo]()
$688
This Delta deal was found by Cheapflights users on 7/21. 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.
Mon 8/246:05 am
MDW
- KIN
1 stop14h 08m
Delta
Thu 9/39:13 am
KIN
- MDW
1 stop7h 02m
Delta
Deal found 7/21![Delta logo]()
$689
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 July 23, 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 July 23, 2026.
This Delta deal was found by Cheapflights users on 7/19. 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 9/309:29 am
MDW
- KIN
2 stops10h 41m
Delta
Sun 10/49:10 am
KIN
- MDW
1 stop13h 34m
Delta
Deal found 7/19![Delta logo]()
$549
This Delta deal was found by Cheapflights users on 7/20. 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.
Fri 8/219:24 am
MDW
- KIN
2 stops10h 49m
Delta
Sun 8/239:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 7/20![Delta logo]()
$549
This Delta deal was found by Cheapflights users on 7/18. 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 9/412:46 pm
MDW
- KIN
1 stop7h 27m
Delta
Mon 9/79:13 am
KIN
- MDW
1 stop7h 02m
Delta
Deal found 7/18![Delta logo]()
$590
This Delta deal was found by Cheapflights users on 7/18. 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 8/1810:54 am
MDW
- KIN
1 stop9h 19m
Delta
Tue 8/259:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 7/18![Delta logo]()
$590
This Delta deal was found by Cheapflights users on 7/18. 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 10/71:00 pm
MDW
- KIN
1 stop6h 30m
Delta
Sat 10/179:00 am
KIN
- MDW
1 stop13h 25m
Delta
Deal found 7/18![Delta logo]()
$590
This Delta deal was found by Cheapflights users on 7/21. 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 9/46:05 am
MDW
- KIN
1 stop14h 08m
Delta
Sun 9/139:10 am
KIN
- MDW
1 stop13h 34m
Delta
Deal found 7/21![Delta logo]()
$590
This Delta deal was found by Cheapflights users on 7/19. 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
MDW
- KIN
1 stop9h 19m
Delta
Wed 9/99:10 am
KIN
- MDW
1 stop13h 34m
Delta
Deal found 7/19![Delta logo]()
$669
Last-minute flights from Midway to KingstonDiscover last-minute flight deals from Midway to Kingston. Data last updated July 23, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Kingston. Data last updated July 23, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/20. 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.
Sat 8/16:00 am
MDW
- KIN
1 stop14h 03m
Delta
Wed 8/59:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 7/20![Delta logo]()
$759
This Delta deal was found by Cheapflights users on 7/20. 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.
Sat 8/16:35 pm
MDW
- KIN
2 stops25h 38m
Delta
Thu 8/69:13 am
KIN
- MDW
2 stops27h 26m
Delta
Deal found 7/20![Delta logo]()
$764
This Delta deal was found by Cheapflights users on 7/19. 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 8/1412:46 pm
MDW
- KIN
1 stop7h 27m
Delta
Wed 8/269:13 am
KIN
- MDW
2 stops9h 20m
Delta
Deal found 7/19![Delta logo]()
$693
This Delta deal was found by Cheapflights users on 7/19. 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 8/1510:56 am
MDW
- KIN
1 stop9h 17m
Delta
Sun 8/309:13 am
KIN
- MDW
1 stop7h 02m
Delta
Deal found 7/19![Delta logo]()
$734
This Delta deal was found by Cheapflights users on 7/18. 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 8/1810:54 am
MDW
- KIN
1 stop9h 19m
Delta
Tue 8/259:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 7/18![Delta logo]()
$590
This Delta deal was found by Cheapflights users on 7/21. 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 8/216:05 am
MDW
- KIN
1 stop14h 08m
Delta
Sun 8/239:13 am
KIN
- MDW
1 stop13h 23m
Delta
Deal found 7/21![Delta logo]()
$544
This Delta deal was found by Cheapflights users on 7/21. 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.
Mon 8/246:05 am
MDW
- KIN
1 stop14h 08m
Delta
Thu 9/39:13 am
KIN
- MDW
1 stop7h 02m
Delta
Deal found 7/21![Delta logo]()
$689
This Delta deal was found by Cheapflights users on 7/21. 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.
Tue 8/259:24 am
MDW
- KIN
2 stops10h 49m
Delta
Thu 9/39:13 am
KIN
- MDW
1 stop7h 02m
Delta
Deal found 7/21![Delta logo]()
$694
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 July 23, 2026.
Search for one-way flight options from Midway to Kingston. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
This Delta deal was found by Cheapflights users on 7/20. 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 8/176:05 am
MDW
- KIN
1 stop14h 08m
Delta
Deal found 7/20![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 7/22. 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 8/76:05 am
MDW
- KIN
1 stop14h 08m
Delta
Deal found 7/22![Delta logo]()
$247
This Delta deal was found by Cheapflights users on 7/18. 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 10/159:29 am
MDW
- KIN
2 stops10h 01m
Delta
Deal found 7/18![Delta logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/711:06 am
MDW
- KIN
3 stops32h 15m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$365
This Delta deal was found by Cheapflights users on 7/21. 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.
Sat 8/19:19 am
MDW
- KIN
2 stops10h 44m
Delta
Deal found 7/21![Delta logo]()
$371
This Delta deal was found by Cheapflights users on 7/22. 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 8/66:05 am
MDW
- KIN
1 stop14h 08m
Delta
Deal found 7/22![Delta logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:05 am
MDW
- KIN
3 stops37h 16m
Multiple Airlines
Deal found 7/20![Multiple Airlines logo]()
$411
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:05 am
MDW
- KIN
3 stops12h 40m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/611:06 am
MDW
- KIN
3 stops31h 39m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 7/18. 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 10/1512:03 pm
MDW
- KIN
3 stops20h 07m
Multiple Airlines
Deal found 7/18![Multiple Airlines logo]()
$418
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 July 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $544 (Delta) |
One-way from | $227 (Delta) |
Popular in | November |
Cheapest in | September |
Average price | $636 |
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 23, 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 - KIN
MDWKIN
Chicago Midway
Wed 9/30
9:29 am-8:10 pm
2 stops10h 41m
Kingston Norman Manley
Sun 10/4
9:10 am-10:44 pm
1 stop13h 34m
$549
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Fri 8/21
9:24 am-8:13 pm
2 stops10h 49m
Kingston Norman Manley
Sun 8/23
9:13 am-10:36 pm
1 stop13h 23m
$549
Quickest round-trip
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Fri 9/4
12:46 pm-8:13 pm
1 stop7h 27m
Kingston Norman Manley
Mon 9/7
9:13 am-4:15 pm
1 stop7h 02m
$590
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Tue 8/18
10:54 am-8:13 pm
1 stop9h 19m
Kingston Norman Manley
Tue 8/25
9:13 am-10:36 pm
1 stop13h 23m
$590
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Wed 10/7
1:00 pm-7:30 pm
1 stop6h 30m
Kingston Norman Manley
Sat 10/17
9:00 am-10:25 pm
1 stop13h 25m
$590
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Fri 9/4
6:05 am-8:13 pm
1 stop14h 08m
Kingston Norman Manley
Sun 9/13
9:10 am-10:44 pm
1 stop13h 34m
$590
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Wed 9/2
10:54 am-8:13 pm
1 stop9h 19m
Kingston Norman Manley
Wed 9/9
9:10 am-10:44 pm
1 stop13h 34m
$669
Cheapest one-way
Quickest one-way
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Fri 8/14
12:46 pm-8:13 pm
1 stop7h 27m
$227
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Sat 8/1
6:00 am-8:03 pm
1 stop14h 03m
$227
ChicagoKingston
MDW - KIN
MDWKIN
Chicago Midway
Mon 8/17
6:05 am-8:13 pm
1 stop14h 08m
$227
Showing 1-10 of 15 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 July.
| 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 July 23, 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.
Boarding
8.1
Entertainment
7.8
Food
7.2
Crew
8.5
Overall
7.8
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Entertainment
7.8
Food
7.2
Crew
8.5
Overall
7.8
Comfort
7.8
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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Find flights from Midway to Kingston, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 July 23, 2026.
Midway and Kingston flights
Browse other Midway and Kingston flight options. Last updated on July 23, 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 July 23, 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 July 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$445 | Average$636 | FlexibilityNo cancel fee | On-timeN/A |