HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$283+ 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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — MDW
Aug 21 — Aug 281
Thu 8/21
Thu 8/28
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from The Big Island to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 August 16, 2025.

Round-trip from

$619
(Southwest)

One-way from

$283
(Delta)
From The Big Island to Chicago Midway
Search Deals
One-way flight from The Big Island to Chicago Midway
Search Deals

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 August 16, 2025.

This Southwest deal was found by Cheapflights users on 8/13. 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 9/248:30 pmKOA - MDW
1 stop10h 15mSouthwest
Mon 9/295:15 amMDW - KOA
1 stop11h 55mSouthwest
Deal found 8/13$576
This Southwest deal was found by Cheapflights users on 8/14. 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.
Thu 9/48:30 pmKOA - MDW
1 stop13h 00mSouthwest
Sun 9/78:20 amMDW - KOA
2 stops14h 50mSouthwest
Deal found 8/14$611
This Southwest deal was found by Cheapflights users on 8/13. 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 11/259:15 pmKOA - MDW
1 stop14h 25mSouthwest
Sun 11/305:35 amMDW - KOA
1 stop12h 00mSouthwest
Deal found 8/13$729
This Southwest deal was found by Cheapflights users on 8/13. 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 8/258:30 pmKOA - MDW
1 stop11h 45mSouthwest
Thu 8/285:15 amMDW - KOA
2 stops14h 10mSouthwest
Deal found 8/13$803
This Southwest deal was found by Cheapflights users on 8/14. 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.
Mon 8/187:00 pmKOA - MDW
2 stops12h 15mSouthwest
Mon 8/255:15 amMDW - KOA
1 stop11h 55mSouthwest
Deal found 8/14$808

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 August 16, 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 9/24

8:30 pm-11:45 am

1 stop10h 15m

Chicago Midway

Mon 9/29

5:15 am-12:10 pm

1 stop11h 55m

$576

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 9/4

6:05 am-11:25 pm

2 stops12h 20m

Chicago Midway

Sun 9/7

8:20 am-6:10 pm

2 stops14h 50m

$617

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 11/25

9:15 pm-3:40 pm

1 stop14h 25m

Chicago Midway

Sun 11/30

5:35 am-1:35 pm

1 stop12h 00m

$729

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Mon 8/25

8:30 pm-1:15 pm

1 stop11h 45m

Chicago Midway

Thu 8/28

5:15 am-2:25 pm

2 stops14h 10m

$803

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Fri 8/29

8:41 pm-6:37 pm

2 stops16h 56m

Chicago Midway

Tue 9/2

9:15 am-7:00 pm

2 stops14h 45m

$845

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 9/4

8:41 pm-6:37 pm

2 stops16h 56m

$283

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 9/4

8:30 pm-11:45 am

1 stop10h 15m

$304

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 9/4

5:15 pm-3:53 pm

3 stops17h 38m

$471

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sat 9/13

8:44 pm-5:35 pm

2 stops15h 51m

$475

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sun 11/30

11:25 pm-10:17 pm

3 stops18h 52m

$954

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 13 results
1
2

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.

  • 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.

  • What is the cheapest month to book a flight from The Big Island to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from The Big Island to Chicago Midway Airport (average of $160). Flying from The Big Island 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.