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Kailua-Kona

$286+ Cheap flights from Midway (MDW) to Kailua-Kona (KOA)

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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KOA
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheap flight deals from Midway to Kailua-Kona

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Kailua-Kona (KOA). 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 29, 2025.

Round-trip from

$584
(Southwest)

One-way from

$286
(Southwest)

Popular in

May

Cheapest in

November

Average price

$891
From Chicago Midway to Kona Intl
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One-way flight from Chicago Midway to Kona Intl
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Highest demand for flights based on searches. 12% potential increase in price ($121 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($50 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 Midway to Kailua-Kona

Cheapest flights from Midway to Kailua-Kona
Explore the most affordable flight options available from Midway to Kailua-Kona. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

This Southwest deal was found by Cheapflights users on 7/28. 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 12/35:15 amMDW - KOA
1 stop12h 25mSouthwest
Wed 12/109:15 pmKOA - MDW
1 stop10h 20mSouthwest
Deal found 7/28$508
This Delta deal was found by Cheapflights users on 7/29. 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 11/46:00 amMDW - KOA
2 stops17h 53mDelta
Thu 11/69:30 pmKOA - MDW
2 stops31h 10mDelta
Deal found 7/29$613

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Kailua-Kona 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 29, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Kailua-Kona that are best for you.

Fly from

Midway

Fly to

Kailua-Kona

Route

Depart

Return

Price

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Fri 9/19

5:15 am-12:10 pm

1 stop11h 55m

Kona Intl

Fri 9/26

9:15 am-5:10 am

2 stops14h 55m

$584

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 9/2

9:30 am-7:00 pm

2 stops14h 30m

Kona Intl

Tue 9/9

8:41 pm-6:37 pm

2 stops16h 56m

$634

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Sun 9/14

10:30 pm-1:05 pm

2 stops19h 35m

$286

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 9/10

6:00 am-7:00 pm

2 stops18h 00m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Best time to book a flight from Midway to Kailua-Kona

Have a flexible travel schedule? Discover the best time to fly to Kailua-Kona from Midway 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 Kailua-Kona

Get insights into the airlines that provide service to Kailua-Kona. 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 Kailua-Kona. Reviews last updated July 29, 2025.
Get a feel of what it's like to fly with Southwest and Delta from Chicago Midway Airport to Kailua-Kona by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,979 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from Midway to Kailua-Kona. 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 into for flights to Kailua-Kona from Chicago Midway?

    Kona Intl (KOA), located 7.7 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Kailua-Kona. 1 airline have flights to Kona Intl from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Kona Intl should not be difficult; the airport handles an average of 0 inbound flights from Chicago Midway per day.

  • What are the cheapest airlines flying from Chicago Midway Airport to Kailua-Kona round-trip?

    Our cheapest airline available from Chicago Midway Airport to Kailua-Kona is Southwest. Our recent data shows that you can find tickets from as low as $584 on this airline. An additional option worth looking into is Delta, starting at $634. Southwest is currently priced 32% below the average price you’ll pay for this route.

  • Can I find deals for flights from Midway to Kailua-Kona that include hotel bookings?

    Yes. In addition to deals on Midway to Kailua-Kona flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Kailua-Kona?

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

  • Can I find deals for business class flights from Midway to Kailua-Kona?

    Yes. Cheapflights offers flight deals from Midway to Kailua-Kona 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 Chicago Midway Airport to Kailua-Kona?

    Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Kailua-Kona (average of $409). Flying from Chicago Midway Airport to Kailua-Kona in June is currently the most expensive (average of $624). 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

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Top airline flying from Midway to Kailua-Kona

Discover the top airline that operate flights from Midway to Kailua-Kona. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$547Average$693FlexibilityNo cancel feeOn-time63%

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