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Kailua-Kona

$219+ Cheap flights from Midway (MDW) to Kailua-Kona (KOA)

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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KOA
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap flight deals from Midway to Kailua-Kona

Cheapest flights from Midway to Kailua-Kona
Explore the most affordable flight options available from Midway to Kailua-Kona. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.

This Southwest deal was found by Cheapflights users on 1/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:55 am
MDW
-
KOA
2 stops14h 15m
Southwest
Fri 2/279:25 pm
KOA
-
MDW
1 stop12h 05m
Southwest
Deal found 1/27$529
This Southwest deal was found by Cheapflights users on 1/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:45 am
MDW
-
KOA
2 stops14h 25m
Southwest
Sat 3/77:05 am
KOA
-
MDW
2 stops13h 05m
Southwest
Deal found 1/24$539
This Delta deal was found by Cheapflights users on 1/26. 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 4/137:16 pm
MDW
-
KOA
2 stops27h 27m
Delta
Mon 4/2010:00 pm
KOA
-
MDW
2 stops14h 58m
Delta
Deal found 1/26$552
This Delta deal was found by Cheapflights users on 1/26. 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 4/117:20 pm
MDW
-
KOA
2 stops27h 27m
Delta
Mon 4/2010:00 pm
KOA
-
MDW
2 stops14h 58m
Delta
Deal found 1/26$577
This Delta deal was found by Cheapflights users on 1/26. 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 4/127:20 pm
MDW
-
KOA
2 stops27h 23m
Delta
Mon 4/2010:00 pm
KOA
-
MDW
2 stops14h 58m
Delta
Deal found 1/26$583
This Southwest deal was found by Cheapflights users on 1/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/125:00 am
MDW
-
KOA
1 stop13h 00m
Southwest
Mon 3/168:25 pm
KOA
-
MDW
1 stop13h 25m
Southwest
Deal found 1/27$589
This Southwest deal was found by Cheapflights users on 1/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:45 am
MDW
-
KOA
1 stop12h 30m
Southwest
Sun 5/310:00 am
KOA
-
MDW
1 stop14h 45m
Southwest
Deal found 1/25$604
This Southwest deal was found by Cheapflights users on 1/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/105:45 am
MDW
-
KOA
2 stops13h 45m
Southwest
Tue 5/1910:00 am
KOA
-
MDW
1 stop14h 45m
Southwest
Deal found 1/24$606
This Southwest deal was found by Cheapflights users on 1/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:45 am
MDW
-
KOA
2 stops14h 25m
Southwest
Sun 3/19:25 pm
KOA
-
MDW
2 stops13h 00m
Southwest
Deal found 1/25$612

Find flight deals from Midway to Kailua-Kona

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Kailua-Kona (KOA). 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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$529
(Southwest)

One-way from

$219
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$593
Provider with most accurate pricing for Chicago Midway-Kona Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Kona Intl flights.
Search Deals
From Chicago Midway to Kona Intl
Search Deals
One-way flight from Chicago Midway to Kona Intl
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Kailua-Kona 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 January 27, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Kailua-Kona that are best for you.

Fly from

Midway

Fly to

Kailua-Kona

Route

Depart

Return

Price

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Fri 2/27

5:00 am-1:45 pm

1 stop12h 45m

Kona Intl

Sat 3/7

7:05 am-12:10 am

2 stops13h 05m

$534

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Sat 4/11

7:20 pm-5:47 pm

2 stops27h 27m

Kona Intl

Mon 4/20

10:00 pm-5:58 pm

2 stops14h 58m

$577

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 3/12

5:00 am-1:00 pm

1 stop13h 00m

Kona Intl

Mon 3/16

8:25 pm-2:50 pm

1 stop13h 25m

$589

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Sun 5/10

5:45 am-2:30 pm

2 stops13h 45m

Kona Intl

Tue 5/19

10:00 am-5:45 am

1 stop14h 45m

$606

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Sun 4/26

5:45 am-6:05 pm

2 stops17h 20m

Kona Intl

Sun 5/3

7:00 pm-12:45 pm

2 stops12h 45m

$637

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 5/11

5:10 am-2:15 pm

2 stops14h 05m

Kona Intl

Mon 5/25

8:25 pm-2:10 pm

1 stop12h 45m

$645

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Fri 4/10

5:10 am-1:15 pm

1 stop13h 05m

Kona Intl

Thu 4/16

8:25 pm-1:10 pm

1 stop11h 45m

$646

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 3/2

7:25 pm-2:47 pm

3 stops47h 22m

$219

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 3/2

8:45 pm-1:15 pm

2 stops20h 30m

$222

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 2/19

12:22 pm-2:11 pm

3 stops29h 49m

$272

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 17 results
1
2

Compare providers for flights from Midway to Kailua-Kona

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 Kailua-Kona in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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-Kailua-Kona 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-Kailua-Kona flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Kailua-Kona flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Kailua-Kona 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-Kailua-Kona 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 Kailua-Kona

Have a flexible travel schedule? Discover the best time to fly to Kailua-Kona 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.

Reviews of airlines servicing Kailua-Kona

Get insights into the airlines that provide service to Kailua-Kona. 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 Kailua-Kona. Reviews last updated January 27, 2026.
Get a feel of what it's like to fly with Southwest from Chicago Midway Airport to Kailua-Kona by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midway to Kailua-Kona. 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 Kailua-Kona from Chicago Midway?

    Kona Intl (KOA), located 7.7 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Kailua-Kona. 1 airline have flights to Kona Intl from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Kona Intl should not be difficult; the airport handles an average of 0 inbound flights from Chicago Midway per day.

  • How long is the flight from Chicago Midway Airport to Kailua-Kona?

    There are many flights that can get you from Chicago Midway Airport to Kailua-Kona in 12h 45m. Fly via Southwest or Delta to get the fastest option. The distance from Chicago Midway Airport to Kailua-Kona is about 4213 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Our cheapest airline available from Chicago Midway Airport to Kailua-Kona is Southwest. Our recent data shows that you can find tickets from as low as $653 on this airline.

  • Can I find deals for flights from Midway to Kailua-Kona that include hotel bookings?

    Yes. In addition to deals on Midway to Kailua-Kona flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Kailua-Kona?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Kailua-Kona.

  • Can I find deals for business class flights from Midway to Kailua-Kona?

    Yes. Cheapflights offers flight deals from Midway to Kailua-Kona by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Top airline flying from Midway to Kailua-Kona

Discover the top airline that operate flights from Midway to Kailua-Kona. 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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$653Average$718FlexibilityNo cancel feeOn-time63%

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