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$242+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — MDW
jan 30 — fev 61
sex 1/30
sex 2/6
1 adult, Economy
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Cheap flight deals from Kailua-Kona to Midway

Best flights from Kailua-Kona to Midway
Discover carefully curated flight deals from Kailua-Kona to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated dezembro 31, 2025.

This Delta deal was found by Cheapflights users on 12/30. 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.
qua 2/1810:55 pmKOA - MDW
2 stops14h 42mDelta
dom 2/229:34 amMDW - KOA
2 stops14h 05mDelta
Deal found 12/30$491
This Southwest deal was found by Cheapflights users on 12/31. 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.
sáb 1/109:25 pmKOA - MDW
2 stops13h 30mSouthwest
sáb 1/175:35 amMDW - KOA
1 stop12h 15mSouthwest
Deal found 12/31$843
This Southwest deal was found by Cheapflights users on 12/31. 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.
sáb 2/77:00 pmKOA - MDW
2 stops13h 35mSouthwest
sáb 2/146:10 amMDW - KOA
2 stops19h 10mSouthwest
Deal found 12/31$859
This Southwest deal was found by Cheapflights users on 12/31. 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.
sáb 1/109:25 pmKOA - MDW
2 stops13h 30mSouthwest
dom 1/186:10 amMDW - KOA
2 stops16h 00mSouthwest
Deal found 12/31$859
This Delta deal was found by Cheapflights users on 12/30. 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.
qua 1/148:45 pmKOA - MDW
2 stops16h 49mDelta
qua 1/216:00 amMDW - KOA
2 stops16h 47mDelta
Deal found 12/30$1,556

Find 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 dezembro 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$491
(Delta)

One-way from

$242
(Delta)

Popular in

March

Cheapest in

February

Average price

$424
Provider with most accurate pricing for Kona Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Kona Intl-Chicago Midway flights.
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From Kona Intl to Chicago Midway
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One-way flight from Kona Intl to Chicago Midway
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Highest demand for flights based on searches. 11% potential increase in price ($90 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($50 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 dezembro 31, 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

qua 2/18

10:55 pm-5:37 pm

2 stops14h 42m

Chicago Midway

dom 2/22

9:34 am-7:39 pm

2 stops14h 05m

$491

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

sáb 1/10

9:25 pm-2:55 pm

2 stops13h 30m

Chicago Midway

sáb 1/17

5:35 am-1:50 pm

1 stop12h 15m

$843

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

sáb 2/7

7:00 pm-12:35 pm

2 stops13h 35m

Chicago Midway

sáb 2/14

6:10 am-9:20 pm

2 stops19h 10m

$859

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

sáb 1/10

9:25 pm-2:55 pm

2 stops13h 30m

Chicago Midway

dom 1/18

6:10 am-6:10 pm

2 stops16h 00m

$859

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

qua 1/14

8:45 pm-5:34 pm

2 stops16h 49m

Chicago Midway

qua 1/21

6:00 am-6:47 pm

2 stops16h 47m

$1,556

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

sex 1/23

8:45 pm-4:16 pm

2 stops15h 31m

$242

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

dom 3/29

9:00 pm-11:45 pm

3 stops21h 45m

$304

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

qua 1/14

6:00 am-12:02 am

3 stops38h 02m

$328

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

sex 1/23

6:38 pm-11:45 am

3 stops37h 07m

$346

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

sex 1/23

9:25 pm-2:40 pm

1 stop13h 15m

$357

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/31

Showing 1-10 of 15 results
1
2
  • Most accurate provider: When it comes to deals on Kailua-Kona-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Kailua-Kona-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Kailua-Kona-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Kailua-Kona-Chicago Midway Airport 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 Kailua-Kona-Chicago Midway Airport 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 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.

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

    Departing from Kailua-Kona to Chicago Midway Airport will take you 13h 30m. The distance from Kailua-Kona to Chicago Midway Airport is about 4213 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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.

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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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