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Kailua-Kona

$224+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KOA
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$537
(Southwest)

One-way from

$224
(Southwest)

Popular in

May

Cheapest in

November

Average price

$653
From Chicago Midway to Kona Intl
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One-way flight from Chicago Midway to Kona Intl
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Highest demand for flights based on searches. 12% potential increase in price ($121 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($50 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. 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 11/169:30 pmMDW - KOA
2 stops19h 15mSouthwest
Sun 11/239:15 pmKOA - MDW
2 stops15h 05mSouthwest
Deal found 9/11$539
This Southwest deal was found by Cheapflights users on 9/11. 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 10/275:40 amMDW - KOA
1 stop12h 20mSouthwest
Sun 11/26:55 pmKOA - MDW
2 stops13h 20mSouthwest
Deal found 9/11$550
This Delta deal was found by Cheapflights users on 9/10. 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 10/259:20 amMDW - KOA
2 stops15h 03mDelta
Sun 11/29:30 pmKOA - MDW
2 stops16h 13mDelta
Deal found 9/10$590
This Delta deal was found by Cheapflights users on 9/11. 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 11/89:20 amMDW - KOA
2 stops14h 33mDelta
Sat 11/158:30 pmKOA - MDW
2 stops17h 38mDelta
Deal found 9/11$591
This Delta deal was found by Cheapflights users on 9/11. 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 9/269:35 amMDW - KOA
2 stops13h 00mDelta
Tue 9/308:44 pmKOA - MDW
2 stops15h 51mDelta
Deal found 9/11$598
This Southwest deal was found by Cheapflights users on 9/10. 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.
Tue 12/25:15 amMDW - KOA
1 stop12h 25mSouthwest
Thu 12/119:15 pmKOA - MDW
2 stops15h 05mSouthwest
Deal found 9/10$619
This Southwest deal was found by Cheapflights users on 9/10. 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.
Sat 10/258:30 amMDW - KOA
2 stops14h 40mSouthwest
Sun 11/29:15 pmKOA - MDW
2 stops13h 45mSouthwest
Deal found 9/10$624
This Delta deal was found by Cheapflights users on 9/10. 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 9/219:29 amMDW - KOA
2 stops13h 06mDelta
Tue 9/308:44 pmKOA - MDW
2 stops15h 51mDelta
Deal found 9/10$629
This Delta deal was found by Cheapflights users on 9/10. 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 10/279:35 amMDW - KOA
2 stops14h 48mDelta
Sun 11/29:30 pmKOA - MDW
2 stops16h 13mDelta
Deal found 9/10$653

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 September 11, 2025.
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

Sun 11/16

9:30 pm-12:45 pm

2 stops19h 15m

Kona Intl

Sun 11/23

9:15 pm-4:20 pm

2 stops15h 05m

$539

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 10/27

5:40 am-1:00 pm

1 stop12h 20m

Kona Intl

Sun 11/2

6:55 pm-12:15 pm

2 stops13h 20m

$550

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Sat 11/8

9:20 am-7:53 pm

2 stops14h 33m

Kona Intl

Sat 11/15

8:30 pm-6:08 pm

2 stops17h 38m

$591

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Fri 9/26

9:35 am-5:35 pm

2 stops13h 00m

Kona Intl

Tue 9/30

8:44 pm-5:35 pm

2 stops15h 51m

$598

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 12/2

5:15 am-1:40 pm

1 stop12h 25m

Kona Intl

Thu 12/11

9:15 pm-4:20 pm

2 stops15h 05m

$619

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Sat 10/25

8:30 am-6:10 pm

2 stops14h 40m

Kona Intl

Sun 11/2

9:15 pm-3:00 pm

2 stops13h 45m

$624

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Sun 9/21

9:29 am-5:35 pm

2 stops13h 06m

Kona Intl

Tue 9/30

8:44 pm-5:35 pm

2 stops15h 51m

$629

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 10/30

5:40 am-1:00 pm

1 stop12h 20m

$224

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 10/30

9:20 am-7:23 pm

2 stops15h 03m

$229

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 10/30

1:37 pm-11:45 am

3 stops27h 08m

$282

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

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 September 11, 2025.
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
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 19h 15m. Fly via Southwest to get the fastest option. The distance from Chicago Midway Airport to Kailua-Kona is about 4213 mi.

  • 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 $631 on this airline. Southwest is currently priced 26% below the average price you’ll pay for this route.

  • 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Kailua-Kona?

    Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Kailua-Kona (average of $409). Flying from Chicago Midway Airport to Kailua-Kona in June is currently the most expensive (average of $624). 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

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$631Average$693FlexibilityNo cancel feeOn-time63%

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