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$266+ Cheap flights from Kailua-Kona (KOA) to Midway (MDW)

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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — MDW
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheap flight deals from Kailua-Kona to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Kailua-Kona (KOA) to Midway (MDW). 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 18, 2025.

Round-trip from

$519
(Southwest)

One-way from

$266
(Delta)
From Kona Intl to Chicago Midway
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One-way flight from Kona Intl to Chicago Midway
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Find flight deals from Kailua-Kona to Midway

Cheapest flights from Kailua-Kona to Midway
Explore the most affordable flight options available from Kailua-Kona to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

This Southwest deal was found by Cheapflights users on 8/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/109:15 pmKOA - MDW
1 stop10h 20mSouthwest
Mon 11/175:15 amMDW - KOA
1 stop12h 25mSouthwest
Deal found 8/17$519
This Southwest deal was found by Cheapflights users on 8/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/168:30 pmKOA - MDW
1 stop11h 45mSouthwest
Tue 9/236:10 amMDW - KOA
1 stop11h 00mSouthwest
Deal found 8/17$582
This Delta deal was found by Cheapflights users on 8/17. 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.
Tue 9/168:44 pmKOA - MDW
2 stops16h 51mDelta
Tue 9/239:35 amMDW - KOA
2 stops13h 00mDelta
Deal found 8/17$608
This Southwest deal was found by Cheapflights users on 8/15. 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 9/168:30 pmKOA - MDW
1 stop10h 15mSouthwest
Mon 9/295:15 amMDW - KOA
1 stop11h 55mSouthwest
Deal found 8/15$619
This Southwest deal was found by Cheapflights users on 8/16. 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.
Wed 9/178:30 pmKOA - MDW
1 stop10h 15mSouthwest
Mon 9/295:15 amMDW - KOA
1 stop11h 55mSouthwest
Deal found 8/16$758
This Southwest deal was found by Cheapflights users on 8/16. 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 8/248:30 pmKOA - MDW
1 stop10h 15mSouthwest
Sat 8/306:15 amMDW - KOA
2 stops16h 55mSouthwest
Deal found 8/16$768

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kailua-Kona to Midway 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 18, 2025.
Use the filters below to find and compare flights from Kailua-Kona to Chicago Midway Airport that are best for you.

Fly from

Kailua-Kona

Fly to

Midway

Route

Depart

Return

Price

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Mon 11/10

9:15 pm-11:35 am

1 stop10h 20m

Chicago Midway

Mon 11/17

5:15 am-1:40 pm

1 stop12h 25m

$519

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 9/16

8:30 pm-1:15 pm

1 stop11h 45m

Chicago Midway

Tue 9/23

6:10 am-12:10 pm

1 stop11h 00m

$582

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 9/16

8:44 pm-6:35 pm

2 stops16h 51m

Chicago Midway

Tue 9/23

9:35 am-5:35 pm

2 stops13h 00m

$608

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 9/16

8:30 pm-11:45 am

1 stop10h 15m

Chicago Midway

Mon 9/29

5:15 am-12:10 pm

1 stop11h 55m

$619

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 9/17

8:30 pm-11:45 am

1 stop10h 15m

Chicago Midway

Mon 9/29

5:15 am-12:10 pm

1 stop11h 55m

$758

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 9/17

8:44 pm-5:35 pm

2 stops15h 51m

Chicago Midway

Mon 9/29

6:00 am-6:41 pm

2 stops17h 41m

$796

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 12/12

8:45 pm-6:36 pm

2 stops17h 51m

$266

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Mon 12/15

9:15 pm-1:40 pm

1 stop12h 25m

$273

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Mon 12/15

8:45 pm-6:07 pm

2 stops17h 22m

$293

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 12/18

9:15 pm-12:15 pm

1 stop11h 00m

$312

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Showing 1-10 of 16 results
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Best time to book a flight from Kailua-Kona to Midway

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

Related info for your journey

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

    Located just 7.7 mi from the city center, Kona Intl is the airport most travelers will use when flying to Chicago Midway from Kailua-Kona. Booking flights from Kona Intl (KOA) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 0 different airlines.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Kailua-Kona to Midway 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 Kailua-Kona to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Kailua-Kona to Chicago Midway Airport (average of $160). Flying from Kailua-Kona to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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