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The Big Island

$259+ 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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KOA
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
1 adult, Economy
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Cheap 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 agosto 14, 2025.

Round-trip from

$434
(Delta)

One-way from

$259
(Delta)

Popular in

March

Cheapest in

September

Average price

$661
From Chicago Midway to The Big Island
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One-way flight from Chicago Midway to The Big Island
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Highest demand for flights based on searches. 2% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 agosto 14, 2025.

This Southwest deal was found by Cheapflights users on 8/12. 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.
dom. 11/95:25 amMDW - KOA
1 stop12h 15mSouthwest
mié. 11/199:15 pmKOA - MDW
1 stop10h 20mSouthwest
Deal found 8/12$409
This Delta deal was found by Cheapflights users on 8/14. 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.
mar. 10/289:20 amMDW - KOA
2 stops15h 03mDelta
mar. 11/49:30 pmKOA - MDW
2 stops16h 13mDelta
Deal found 8/14$434
This Southwest deal was found by Cheapflights users on 8/12. 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.
mar. 11/115:15 amMDW - KOA
1 stop12h 25mSouthwest
mié. 11/199:15 pmKOA - MDW
1 stop10h 20mSouthwest
Deal found 8/12$454
This Delta deal was found by Cheapflights users on 8/13. 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.
mar. 9/239:35 amMDW - KOA
2 stops13h 00mDelta
mar. 9/308:44 pmKOA - MDW
2 stops15h 51mDelta
Deal found 8/13$487
This Delta deal was found by Cheapflights users on 8/13. 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.
lun. 10/279:20 amMDW - KOA
2 stops15h 03mDelta
mar. 11/49:30 pmKOA - MDW
2 stops16h 13mDelta
Deal found 8/13$504
This Southwest deal was found by Cheapflights users on 8/13. 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.
mié. 11/125:15 amMDW - KOA
2 stops16h 55mSouthwest
mié. 11/199:15 pmKOA - MDW
1 stop10h 20mSouthwest
Deal found 8/13$513
This Southwest deal was found by Cheapflights users on 8/14. 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.
mar. 10/286:05 amMDW - KOA
1 stop11h 55mSouthwest
mar. 11/49:15 pmKOA - MDW
1 stop12h 25mSouthwest
Deal found 8/14$522
This Southwest deal was found by Cheapflights users on 8/12. 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.
lun. 10/275:40 amMDW - KOA
1 stop12h 20mSouthwest
mar. 11/49:15 pmKOA - MDW
1 stop12h 25mSouthwest
Deal found 8/12$524
This Southwest deal was found by Cheapflights users on 8/13. 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.
vie. 10/247:45 amMDW - ITO
2 stops15h 25mSouthwest
vie. 10/316:55 pmITO - MDW
2 stops16h 55mSouthwest
Deal found 8/13$652
This Southwest deal was found by Cheapflights users on 8/13. 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.
lun. 8/255:15 amMDW - ITO
2 stops17h 55mSouthwest
lun. 9/86:55 pmITO - MDW
2 stops14h 00mSouthwest
Deal found 8/13$754
This Southwest deal was found by Cheapflights users on 8/14. 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.
dom. 8/175:30 amMDW - ITO
2 stops14h 10mSouthwest
dom. 8/316:00 amITO - MDW
2 stops12h 25mSouthwest
Deal found 8/14$944
This Delta deal was found by Cheapflights users on 8/13. 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.
sáb. 9/271:43 pmMDW - ITO
2 stops35h 47mDelta
lun. 9/2912:20 pmITO - MDW
2 stops24h 15mDelta
Deal found 8/13$945

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 agosto 14, 2025.
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

dom. 11/9

5:25 am-1:40 pm

1 stop12h 15m

Kona Intl

mié. 11/19

9:15 pm-11:35 am

1 stop10h 20m

$409

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

mar. 10/28

9:20 am-7:23 pm

2 stops15h 03m

Kona Intl

mar. 11/4

9:30 pm-5:43 pm

2 stops16h 13m

$434

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

mar. 11/11

5:15 am-1:40 pm

1 stop12h 25m

Kona Intl

mié. 11/19

9:15 pm-11:35 am

1 stop10h 20m

$454

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

mar. 9/23

9:35 am-5:35 pm

2 stops13h 00m

Kona Intl

mar. 9/30

8:44 pm-5:35 pm

2 stops15h 51m

$487

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

lun. 10/27

9:20 am-7:23 pm

2 stops15h 03m

Kona Intl

mar. 11/4

9:30 pm-5:43 pm

2 stops16h 13m

$504

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

mié. 11/12

5:15 am-6:10 pm

2 stops16h 55m

Kona Intl

mié. 11/19

9:15 pm-11:35 am

1 stop10h 20m

$513

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

mar. 10/28

6:05 am-1:00 pm

1 stop11h 55m

Kona Intl

mar. 11/4

9:15 pm-1:40 pm

1 stop12h 25m

$522

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

lun. 10/27

5:40 am-1:00 pm

1 stop12h 20m

Kona Intl

mar. 11/4

9:15 pm-1:40 pm

1 stop12h 25m

$524

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

vie. 10/24

7:45 am-6:10 pm

2 stops15h 25m

Hilo Intl

vie. 10/31

6:55 pm-4:50 pm

2 stops16h 55m

$652

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

mar. 8/26

6:10 am-6:10 pm

2 stops17h 00m

Hilo Intl

mar. 9/9

6:55 pm-1:15 pm

2 stops13h 20m

$754

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 24 results
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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 agosto 14, 2025.
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
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to The Big Island?

    Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to The Big Island (average of $409). Flying from Chicago Midway Airport to The Big Island 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

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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$547Average$693FlexibilityNo cancel feeOn-time63%

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