HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kailua-Kona

$308+ 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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KOA
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Kailua-Kona 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 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 December 16, 2025.

This Southwest deal was found by Cheapflights users on 12/13. 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 12/175:15 amMDW - KOA
1 stop12h 25mSouthwest
Fri 12/199:15 pmKOA - MDW
1 stop12h 25mSouthwest
Deal found 12/13$858
This Delta deal was found by Cheapflights users on 12/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/179:59 amMDW - KOA
2 stops13h 31mDelta
Fri 12/199:30 pmKOA - MDW
2 stops15h 49mDelta
Deal found 12/13$894
This Southwest deal was found by Cheapflights users on 12/15. 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 12/315:15 amMDW - KOA
1 stop12h 25mSouthwest
Tue 1/69:25 pmKOA - MDW
1 stop15h 10mSouthwest
Deal found 12/15$998
This Southwest deal was found by Cheapflights users on 12/15. 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 12/295:10 amMDW - KOA
1 stop12h 30mSouthwest
Mon 12/299:15 pmKOA - MDW
1 stop11h 00mSouthwest
Deal found 12/15$1,053
This Southwest deal was found by Cheapflights users on 12/13. 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.
Sun 12/285:40 amMDW - KOA
1 stop12h 00mSouthwest
Mon 1/59:15 pmKOA - MDW
1 stop11h 20mSouthwest
Deal found 12/13$1,133
This Southwest deal was found by Cheapflights users on 12/15. 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 12/225:10 amMDW - KOA
1 stop12h 30mSouthwest
Mon 12/299:15 pmKOA - MDW
1 stop11h 00mSouthwest
Deal found 12/15$1,138

Find 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 December 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$464
(Delta)

One-way from

$308
(Delta)

Popular in

December

Cheapest in

September

Average price

$1,118
Provider with most accurate pricing for Chicago Midway-Kona Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Kona Intl flights.
Search Deals
From Chicago Midway to Kona Intl
Search Deals
One-way flight from Chicago Midway to Kona Intl
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 16, 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

Tue 3/3

6:00 am-7:34 pm

2 stops17h 34m

Kona Intl

Mon 3/9

8:55 pm-5:55 pm

2 stops16h 00m

$464

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 1/27

6:10 am-1:45 pm

1 stop11h 35m

Kona Intl

Tue 2/3

9:25 pm-2:45 pm

2 stops13h 20m

$530

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Sun 2/22

9:34 am-7:34 pm

2 stops14h 00m

Kona Intl

Sun 3/1

9:45 pm-5:37 pm

2 stops15h 52m

$565

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Fri 1/23

6:10 am-1:45 pm

1 stop11h 35m

Kona Intl

Fri 1/30

9:25 pm-11:50 am

1 stop10h 25m

$569

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 2/25

9:34 am-7:34 pm

2 stops14h 00m

Kona Intl

Tue 3/3

9:45 pm-5:37 pm

2 stops15h 52m

$599

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 3/3

6:10 am-1:45 pm

1 stop11h 35m

Kona Intl

Mon 3/9

8:25 pm-2:50 pm

1 stop13h 25m

$609

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Sun 2/22

5:00 am-1:45 pm

1 stop12h 45m

Kona Intl

Sun 3/1

7:00 pm-12:30 pm

2 stops13h 30m

$624

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 12/31

9:29 am-6:30 pm

2 stops37h 01m

$324

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 1/1

5:25 am-9:20 pm

2 stops19h 55m

$347

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 12/31

5:15 am-1:40 pm

1 stop12h 25m

$437

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 14 results
1
2

Compare providers for flights from Midway to Kailua-Kona

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Kailua-Kona in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Kailua-Kona flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Kailua-Kona flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Kailua-Kona flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Kailua-Kona flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Kailua-Kona flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

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. 0 airlines 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.

  • How long is the flight from Chicago Midway Airport to Kailua-Kona?

    There are many flights that can get you from Chicago Midway Airport to Kailua-Kona in 11h 35m. Fly via Delta or Southwest to get the fastest option. The distance from Chicago Midway Airport to Kailua-Kona 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 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.

See more FAQs

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.