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$257+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — MDW
Nov 1 — Nov 81
Sat 11/1
Sat 11/8
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 October 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$647
(Delta)

One-way from

$257
(Delta)

Popular in

March

Cheapest in

October

Average price

$455
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. 23% potential increase in price ($230 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($55 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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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 October 2, 2025.

This Delta deal was found by Cheapflights users on 10/2. 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 11/248:53 pmKOA - MDW
2 stops17h 25mDelta
Tue 12/29:59 amMDW - KOA
2 stops13h 31mDelta
Deal found 10/2$647
This Delta deal was found by Cheapflights users on 10/2. 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 10/178:30 pmKOA - MDW
2 stops16h 55mDelta
Tue 10/219:20 amMDW - KOA
2 stops15h 03mDelta
Deal found 10/2$862
This Delta deal was found by Cheapflights users on 9/30. 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.
Thu 10/169:30 pmKOA - MDW
2 stops15h 13mDelta
Mon 10/206:00 amMDW - KOA
2 stops18h 12mDelta
Deal found 9/30$1,016
This Delta deal was found by Cheapflights users on 9/30. 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.
Thu 10/912:38 pmKOA - MDW
2 stops15h 02mDelta
Sun 10/126:00 amMDW - KOA
2 stops18h 12mDelta
Deal found 9/30$1,236
This Delta deal was found by Cheapflights users on 10/2. 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 10/168:30 pmKOA - MDW
2 stops16h 13mDelta
Sun 10/199:20 amMDW - KOA
2 stops15h 03mDelta
Deal found 10/2$1,970

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 October 2, 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 11/24

8:53 pm-6:18 pm

2 stops17h 25m

Chicago Midway

Tue 12/2

9:59 am-7:30 pm

2 stops13h 31m

$647

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 10/17

8:30 pm-6:25 pm

2 stops16h 55m

Chicago Midway

Tue 10/21

9:20 am-7:23 pm

2 stops15h 03m

$862

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 10/16

9:30 pm-5:43 pm

2 stops15h 13m

Chicago Midway

Mon 10/20

6:00 am-7:12 pm

2 stops18h 12m

$1,016

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 10/16

8:30 pm-5:43 pm

2 stops16h 13m

Chicago Midway

Sun 10/19

9:20 am-7:23 pm

2 stops15h 03m

$1,970

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 11/14

9:30 pm-6:18 pm

2 stops16h 48m

$257

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 3/18

10:00 am-5:45 am

1 stop14h 45m

$322

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 3/20

10:00 am-5:45 am

1 stop14h 45m

$382

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 1/8

9:45 pm-6:08 pm

2 stops16h 23m

$387

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Mon 3/23

9:55 pm-6:34 pm

2 stops15h 39m

$387

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sat 1/31

9:45 pm-6:08 pm

2 stops16h 23m

$405

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/30

Showing 1-10 of 11 results
1
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  • 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 17h 25m. The distance from Kailua-Kona to Chicago Midway Airport is about 4213 mi.

  • 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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