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$197+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — MDW
Mar 18 — Mar 251
Wed 3/18
Wed 3/25
1 adult, Economy
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Cheap 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 February 16, 2026.

This Delta deal was found by Cheapflights users on 2/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2310:07 pm
KOA
-
MDW
2 stops15h 29m
Delta
Tue 4/289:27 am
MDW
-
KOA
2 stops14h 36m
Delta
Deal found 2/16$655
This Southwest deal was found by Cheapflights users on 2/12. 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 2/2810:00 am
KOA
-
MDW
2 stops15h 05m
Southwest
Wed 3/46:10 am
MDW
-
KOA
1 stop11h 35m
Southwest
Deal found 2/12$692
This Southwest deal was found by Cheapflights users on 2/14. 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 3/19:25 pm
KOA
-
MDW
1 stop12h 20m
Southwest
Thu 3/55:00 am
MDW
-
KOA
1 stop13h 00m
Southwest
Deal found 2/14$714
This Southwest deal was found by Cheapflights users on 2/15. 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.
Mon 3/29:25 pm
KOA
-
MDW
1 stop11h 10m
Southwest
Fri 3/69:30 pm
MDW
-
KOA
1 stop18h 25m
Southwest
Deal found 2/15$739
This Delta deal was found by Cheapflights users on 2/12. 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.
Wed 2/1810:55 pm
KOA
-
MDW
2 stops14h 42m
Delta
Sun 2/229:34 am
MDW
-
KOA
2 stops14h 05m
Delta
Deal found 2/12$809
This Delta deal was found by Cheapflights users on 2/14. 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 10/28:40 pm
KOA
-
MDW
2 stops16h 25m
Delta
Fri 10/91:05 pm
MDW
-
KOA
2 stops33h 49m
Delta
Deal found 2/14$832

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 February 16, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$545
(Delta)

One-way from

$197
(Kiwi.com)

Popular in

March

Cheapest in

February

Average price

$421
Provider with most accurate pricing for Kona Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Kona Intl-Chicago (CHI) flights.
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From Kona Intl to Chicago Midway
Search Deals
One-way flight from Kona Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($93 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 February 2026
Search Deals

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 February 16, 2026.
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

Thu 4/23

10:07 pm-6:36 pm

2 stops15h 29m

Chicago Midway

Tue 4/28

9:27 am-7:03 pm

2 stops14h 36m

$655

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sat 2/28

10:00 am-5:05 am

2 stops15h 05m

Chicago Midway

Wed 3/4

6:10 am-1:45 pm

1 stop11h 35m

$692

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sun 3/1

9:25 pm-1:45 pm

1 stop12h 20m

Chicago Midway

Thu 3/5

5:00 am-2:00 pm

1 stop13h 00m

$714

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Mon 3/2

9:25 pm-12:35 pm

1 stop11h 10m

Chicago Midway

Fri 3/6

9:30 pm-11:55 am

1 stop18h 25m

$739

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 3/18

8:25 pm-1:35 pm

1 stop12h 10m

Chicago Midway

Sun 3/22

5:00 am-1:00 pm

1 stop13h 00m

$861

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 4/7

10:15 pm-5:54 pm

2 stops14h 39m

Chicago Midway

Sun 4/12

6:00 am-7:16 pm

2 stops18h 16m

$868

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 4/14

6:56 pm-2:49 pm

3 stops38h 53m

$230

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 4/30

8:25 pm-1:10 pm

1 stop11h 45m

$317

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 4/16

7:10 am-2:49 pm

2 stops26h 39m

$320

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 5/1

10:07 pm-6:36 pm

2 stops15h 29m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/14

Showing 1-10 of 17 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.

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

    Departing from Kailua-Kona to Chicago Midway Airport will take you 15h 05m. 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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