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$234+ Cheap flights from The Big Island 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 3/16. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — MDW
Feb 22 — Mar 11
Sun 2/22
Sun 3/1
1 adult, Economy
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Cheap flight deals from The Big Island to Midway

Cheapest flights from The Big Island to Midway
Explore the most affordable flight options available from The Big Island to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 23, 2026.

This Delta deal was found by Cheapflights users on 1/21. 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 1/21$530
This Delta deal was found by Cheapflights users on 1/21. 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 2/129:55 pm
KOA
-
MDW
2 stops15h 42m
Delta
Tue 2/249:34 am
MDW
-
KOA
2 stops14h 05m
Delta
Deal found 1/21$555
This Delta deal was found by Cheapflights users on 1/22. 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 4/710:15 pm
KOA
-
MDW
2 stops14h 39m
Delta
Mon 4/136:34 pm
MDW
-
KOA
2 stops28h 09m
Delta
Deal found 1/22$602
This Delta deal was found by Cheapflights users on 1/23. 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 2/179:55 pm
KOA
-
MDW
2 stops15h 42m
Delta
Thu 2/269:34 am
MDW
-
KOA
2 stops14h 05m
Delta
Deal found 1/23$665
This Delta deal was found by Cheapflights users on 1/22. 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 2/168:55 pm
KOA
-
MDW
2 stops17h 45m
Delta
Thu 2/269:34 am
MDW
-
KOA
2 stops14h 05m
Delta
Deal found 1/22$683
This Delta deal was found by Cheapflights users on 1/22. 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 2/68:55 pm
KOA
-
MDW
2 stops14h 43m
Delta
Tue 2/109:33 am
MDW
-
KOA
2 stops14h 24m
Delta
Deal found 1/22$774
This Delta deal was found by Cheapflights users on 1/21. 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 4/710:15 pm
KOA
-
MDW
2 stops14h 39m
Delta
Sun 4/126:00 am
MDW
-
KOA
2 stops18h 16m
Delta
Deal found 1/21$778

Find flight deals from The Big Island to Midway

Keep the following information in mind while searching for The Big Island to Midway flight deals. Data was last updated January 23, 2026.

Round-trip from

$530
(Delta)

One-way from

$234
(Southwest)
From The Big Island to Chicago Midway
Search Deals
One-way flight from The Big Island to Chicago Midway
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from The Big Island 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 January 23, 2026.
Use the filters below to find and compare flights from The Big Island to Chicago Midway Airport that are best for you.

Fly from

The Big Island

Fly to

Midway

Route

Depart

Return

Price

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 2/18

10:55 pm-5:37 pm

2 stops14h 42m

Chicago Midway

Sun 2/22

9:34 am-7:39 pm

2 stops14h 05m

$530

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 2/12

9:55 pm-5:37 pm

2 stops15h 42m

Chicago Midway

Tue 2/24

9:34 am-7:39 pm

2 stops14h 05m

$555

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 4/7

10:15 pm-5:54 pm

2 stops14h 39m

Chicago Midway

Mon 4/13

6:34 pm-5:43 pm

2 stops28h 09m

$602

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 2/17

9:55 pm-5:37 pm

2 stops15h 42m

Chicago Midway

Thu 2/26

9:34 am-7:39 pm

2 stops14h 05m

$665

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Mon 2/16

8:55 pm-6:40 pm

2 stops17h 45m

Chicago Midway

Thu 2/26

9:34 am-7:39 pm

2 stops14h 05m

$683

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 2/6

8:55 pm-3:38 pm

2 stops14h 43m

Chicago Midway

Tue 2/10

9:33 am-7:57 pm

2 stops14h 24m

$774

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

$778

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Mon 3/16

8:25 pm-11:55 am

1 stop10h 30m

$234

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 4/1

10:00 am-5:00 am

2 stops14h 00m

$250

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 5/1

10:00 am-5:45 am

1 stop14h 45m

$262

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 15 results
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Best time to book a flight from The Big Island to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from The Big Island 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.

Cheapflights Insights

Everything you need to know about your flight from The Big Island to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from The Big Island to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from The Big Island to Chicago Midway Airport?

    A quick flight from The Big Island to Chicago Midway Airport can take about 14h 42m. Delta provides one of the quickest options available for as low as $530. The distance between The Big Island and Chicago Midway Airport is about 4213 mi.

  • Can I find deals for flights from The Big Island to Midway that include hotel bookings?

    Yes. In addition to deals on The Big Island to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from The Big Island to Midway?

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

  • Can I find deals for business class flights from The Big Island to Midway?

    Yes. Cheapflights offers flight deals from The Big Island 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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