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Midway

$337+ 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — MDW
Jul 16 — Jul 231
Wed 7/16
Wed 7/23
1 adult, Economy
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Cheap 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 July 11, 2025.

Round-trip from

$763
(Southwest)

One-way from

$337
(Delta)

Popular in

March

Cheapest in

September

Average price

$746
From Kona Intl to Chicago Midway
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One-way flight from Kona Intl to Chicago Midway
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Highest demand for flights based on searches. 24% potential increase in price ($237 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($56 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find 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 July 11, 2025.

This Southwest deal was found by Cheapflights users on 7/10. 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 12/209:15 pmKOA - MDW
1 stop11h 00mSouthwest
Thu 1/15:15 amMDW - KOA
1 stop12h 25mSouthwest
Deal found 7/10$763
This Delta deal was found by Cheapflights users on 7/10. 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.
Sat 12/2010:55 pmKOA - MDW
2 stops14h 42mDelta
Thu 1/19:30 amMDW - KOA
2 stops14h 20mDelta
Deal found 7/10$914

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 July 11, 2025.
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

Sat 12/20

9:15 pm-12:15 pm

1 stop11h 00m

Chicago Midway

Thu 1/1

5:15 am-1:40 pm

1 stop12h 25m

$763

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sat 12/20

10:55 pm-5:37 pm

2 stops14h 42m

Chicago Midway

Thu 1/1

9:30 am-7:50 pm

2 stops14h 20m

$914

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sun 9/28

8:44 pm-6:35 pm

2 stops16h 51m

$337

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sat 10/4

8:30 pm-3:25 pm

2 stops13h 55m

$352

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/10

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.

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 July 11, 2025.
See what other customers who have flown with Southwest and Delta from Kailua-Kona to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

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
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

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
7,952 reviews
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.6

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 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.

  • 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.

  • What is the cheapest month to book a flight from Kailua-Kona to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Kailua-Kona to Chicago Midway Airport (average of $160). Flying from Kailua-Kona 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 Kailua-Kona?

Book flights to Kailua-Kona if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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