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$318+ 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — MDW
Nov 9 — Nov 161
Sun 11/9
Sun 11/16
1 adult, Economy
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Find 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 October 10, 2025.

This Southwest deal was found by Cheapflights users on 10/9. 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 11/269:15 pmKOA - MDW
1 stop16h 35mSouthwest
Sun 11/305:35 amMDW - KOA
2 stops16h 35mSouthwest
Deal found 10/9$798
This Delta deal was found by Cheapflights users on 10/9. 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 10/248:30 pmKOA - MDW
2 stops16h 13mDelta
Tue 10/289:35 amMDW - KOA
2 stops14h 48mDelta
Deal found 10/9$974
This Southwest deal was found by Cheapflights users on 10/8. 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 12/166:55 pmKOA - MDW
2 stops12h 40mSouthwest
Tue 12/235:10 amMDW - KOA
1 stop12h 30mSouthwest
Deal found 10/8$1,285
This Delta deal was found by Cheapflights users on 10/7. 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 11/118:30 pmKOA - MDW
2 stops17h 48mDelta
Sun 11/169:41 amMDW - KOA
2 stops13h 44mDelta
Deal found 10/7$3,199

Cheap 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 October 10, 2025.

Round-trip from

$703
(Delta)

One-way from

$392
(Delta)
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 October 10, 2025.
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 11/26

9:15 pm-5:50 pm

1 stop16h 35m

Chicago Midway

Sun 11/30

5:35 am-6:10 pm

2 stops16h 35m

$798

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 10/24

8:30 pm-5:43 pm

2 stops16h 13m

Chicago Midway

Tue 10/28

9:35 am-7:23 pm

2 stops14h 48m

$974

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 12/16

6:55 pm-11:35 am

2 stops12h 40m

Chicago Midway

Tue 12/23

5:10 am-1:40 pm

1 stop12h 30m

$1,285

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 11/11

8:30 pm-6:18 pm

2 stops17h 48m

Chicago Midway

Sun 11/16

9:41 am-7:25 pm

2 stops13h 44m

$3,199

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sun 2/8

9:25 pm-2:55 pm

2 stops13h 30m

$318

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sat 1/31

9:45 pm-6:08 pm

2 stops16h 23m

$392

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

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 16h 13m. Southwest provides one of the quickest options available for as low as $974. The distance between The Big Island and Chicago Midway Airport is about 4213 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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