HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
The Big Island

$236+ Cheap flights from Midway (MDW) to The Big Island

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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KOA
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to The Big Island 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 The Big Island

Cheapest flights from Midway to The Big Island
Explore the most affordable flight options available from Midway to The Big Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This Southwest deal was found by Cheapflights users on 1/20. 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 3/27:55 am
MDW
-
KOA
2 stops17h 25m
Southwest
Wed 3/49:25 pm
KOA
-
MDW
2 stops12h 50m
Southwest
Deal found 1/20$433
This Southwest deal was found by Cheapflights users on 1/19. 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 2/98:10 am
MDW
-
KOA
2 stops14h 00m
Southwest
Fri 2/137:00 pm
KOA
-
MDW
2 stops14h 25m
Southwest
Deal found 1/19$464
This Southwest deal was found by Cheapflights users on 1/20. 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.
Fri 2/207:45 am
MDW
-
KOA
2 stops14h 25m
Southwest
Wed 2/259:25 pm
KOA
-
MDW
1 stop13h 35m
Southwest
Deal found 1/20$481
This Southwest deal was found by Cheapflights users on 1/19. 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 2/267:45 am
MDW
-
KOA
2 stops14h 25m
Southwest
Wed 3/49:25 pm
KOA
-
MDW
1 stop12h 10m
Southwest
Deal found 1/19$487
This Southwest deal was found by Cheapflights users on 1/19. 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 2/186:10 am
MDW
-
KOA
2 stops16h 00m
Southwest
Wed 2/259:25 pm
KOA
-
MDW
1 stop13h 35m
Southwest
Deal found 1/19$506
This Southwest deal was found by Cheapflights users on 1/20. 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 3/28:45 pm
MDW
-
KOA
2 stops20h 30m
Southwest
Thu 3/511:00 am
KOA
-
MDW
1 stop14h 45m
Southwest
Deal found 1/20$534
This Delta deal was found by Cheapflights users on 1/20. 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.
Mon 3/99:35 am
MDW
-
KOA
2 stops14h 02m
Delta
Wed 3/1810:15 pm
KOA
-
MDW
2 stops14h 39m
Delta
Deal found 1/20$535
This Southwest deal was found by Cheapflights users on 1/19. 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 2/186:10 am
MDW
-
ITO
2 stops16h 00m
Southwest
Wed 2/256:55 pm
ITO
-
MDW
2 stops12h 55m
Southwest
Deal found 1/19$577
This Southwest deal was found by Cheapflights users on 1/18. 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 2/178:35 pm
MDW
-
ITO
2 stops22h 05m
Southwest
Tue 2/246:55 pm
ITO
-
MDW
2 stops13h 40m
Southwest
Deal found 1/18$592
This Southwest deal was found by Cheapflights users on 1/19. 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 2/238:35 pm
MDW
-
ITO
2 stops22h 05m
Southwest
Sun 3/16:55 pm
ITO
-
MDW
2 stops13h 35m
Southwest
Deal found 1/19$624
This Southwest deal was found by Cheapflights users on 1/18. 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 3/1210:05 am
MDW
-
ITO
2 stops16h 35m
Southwest
Tue 3/176:55 pm
ITO
-
MDW
2 stops12h 00m
Southwest
Deal found 1/18$685
This Southwest deal was found by Cheapflights users on 1/19. 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 2/75:35 am
MDW
-
ITO
2 stops16h 35m
Southwest
Tue 2/106:55 pm
ITO
-
MDW
2 stops13h 40m
Southwest
Deal found 1/19$692

Find flight deals from Midway to The Big Island

Keep the following information in mind while searching for Midway to The Big Island flight deals. Data was last updated January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$433
(Southwest)

One-way from

$236
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$598
Provider with most accurate pricing for Chicago (CHI)-Kona Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Kona Intl flights.
Search Deals
From Chicago Midway to The Big Island
Search Deals
One-way flight from Chicago Midway to The Big Island
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to The Big Island 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 January 21, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to The Big Island that are best for you.

Fly from

Midway

Fly to

The Big Island

Route

Depart

Return

Price

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 3/2

7:55 am-9:20 pm

2 stops17h 25m

Kona Intl

Wed 3/4

9:25 pm-1:35 pm

1 stop12h 10m

$459

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Fri 2/20

7:45 am-6:10 pm

2 stops14h 25m

Kona Intl

Wed 2/25

9:25 pm-3:05 pm

2 stops13h 40m

$486

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 2/26

7:45 am-6:10 pm

2 stops14h 25m

Kona Intl

Wed 3/4

9:25 pm-1:35 pm

1 stop12h 10m

$487

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 2/18

6:10 am-9:20 pm

2 stops19h 10m

Kona Intl

Wed 2/25

9:25 pm-3:05 pm

2 stops13h 40m

$511

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 3/2

8:45 pm-1:15 pm

2 stops20h 30m

Kona Intl

Thu 3/5

11:00 am-5:45 am

1 stop14h 45m

$534

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 3/9

9:35 am-6:37 pm

2 stops14h 02m

Kona Intl

Wed 3/18

10:15 pm-5:54 pm

2 stops14h 39m

$535

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 2/9

8:10 am-6:10 pm

2 stops14h 00m

Kona Intl

Fri 2/13

9:25 pm-3:00 pm

1 stop13h 35m

$574

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Wed 2/18

6:10 am-6:10 pm

2 stops16h 00m

Hilo Intl

Wed 2/25

6:55 pm-11:50 am

2 stops12h 55m

$577

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Tue 2/17

8:35 pm-2:40 pm

2 stops22h 05m

Hilo Intl

Tue 2/24

6:55 pm-12:35 pm

2 stops13h 40m

$592

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Mon 2/23

8:35 pm-2:40 pm

2 stops22h 05m

Hilo Intl

Sun 3/1

6:55 pm-12:30 pm

2 stops13h 35m

$624

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 39 results
1
2
3
4

Best time to book a flight from Midway to The Big Island

Have a flexible travel schedule? Discover the best time to fly to The Big Island 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to The Big Island
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing The Big Island

Get insights into the airlines that provide service to The Big Island. 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 The Big Island. Reviews last updated January 21, 2026.
Read reviews from past customers who have flown Southwest from Chicago Midway Airport to The Big Island. 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
4,266 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midway to The Big Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to The Big Island?

    There are many flights that can get you from Chicago Midway Airport to The Big Island in 17h 25m. Fly via Southwest to get the fastest option. The distance between Chicago Midway Airport and The Big Island is about 4213 mi.

  • Can I find deals for flights from Midway to The Big Island that include hotel bookings?

    Yes. In addition to deals on Midway to The Big Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to The Big Island?

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

  • Can I find deals for business class flights from Midway to The Big Island?

    Yes. Cheapflights offers flight deals from Midway to The Big Island 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.

Top airline flying from Midway to The Big Island

Discover the top airline that operate flights from Midway to The Big Island. 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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$653Average$718FlexibilityNo cancel feeOn-time63%

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.