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Midway

$238+ 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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — MDW
Jul 1 — Jul 81
Tue 7/1
Tue 7/8
1 adult, Economy
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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 June 26, 2025.

Round-trip from

$743
(Southwest)

One-way from

$238
(Southwest)
From The Big Island to Chicago Midway
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One-way flight from The Big Island to Chicago Midway
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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 June 26, 2025.

This Southwest deal was found by Cheapflights users on 6/25. 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 8/78:30 pmKOA - MDW
2 stops13h 10mSouthwest
Sat 8/166:15 amMDW - KOA
1 stop10h 55mSouthwest
Deal found 6/25$743
This Delta deal was found by Cheapflights users on 6/26. 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 8/68:35 pmKOA - MDW
2 stops16h 04mDelta
Tue 8/126:04 amMDW - KOA
2 stops16h 37mDelta
Deal found 6/26$1,017

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 June 26, 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

Thu 8/7

8:30 pm-2:40 pm

2 stops13h 10m

Chicago Midway

Sat 8/16

6:15 am-12:10 pm

1 stop10h 55m

$743

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 8/6

8:35 pm-5:39 pm

2 stops16h 04m

Chicago Midway

Tue 8/12

6:04 am-5:41 pm

2 stops16h 37m

$1,017

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 9/3

7:00 pm-1:25 pm

2 stops13h 25m

$238

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sun 8/17

9:47 pm-5:37 pm

2 stops14h 50m

$367

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/25

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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated June 26, 2025.
Read through reviews of airlines operating flights from The Big Island to Chicago Midway Airport, such as Southwest and Delta. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,276 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,276 reviews
Southwest
8.0
Very good
4,276 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,964 reviews
Southwest
8.0
Very good
4,276 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Food

7.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 The Big Island?

Book flights to The Big Island if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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