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The Big Island

$223+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KOA
ene. 8 — ene. 151
jue. 1/8
jue. 1/15
1 adult, Economy
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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 diciembre 9, 2025.

This Southwest deal was found by Cheapflights users on 12/7. 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. 12/85:15 amMDW - KOA
1 stop12h 25mSouthwest
dom. 12/149:15 pmKOA - MDW
1 stop10h 20mSouthwest
Deal found 12/7$752
This Southwest deal was found by Cheapflights users on 12/7. 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. 12/155:15 amMDW - KOA
2 stops16h 55mSouthwest
mar. 12/239:15 pmKOA - MDW
1 stop12h 25mSouthwest
Deal found 12/7$783
This Southwest deal was found by Cheapflights users on 12/7. 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. 12/155:15 amMDW - KOA
2 stops16h 55mSouthwest
sáb. 12/209:15 pmKOA - MDW
1 stop11h 00mSouthwest
Deal found 12/7$797
This Southwest deal was found by Cheapflights users on 12/7. 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. 12/147:55 amMDW - KOA
2 stops17h 25mSouthwest
vie. 12/199:15 pmKOA - MDW
1 stop14h 20mSouthwest
Deal found 12/7$808
This Southwest deal was found by Cheapflights users on 12/8. 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.
sáb. 12/138:15 amMDW - KOA
2 stops13h 55mSouthwest
sáb. 12/209:15 pmKOA - MDW
1 stop11h 00mSouthwest
Deal found 12/8$832
This Southwest deal was found by Cheapflights users on 12/7. 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. 12/147:55 amMDW - ITO
2 stops17h 45mSouthwest
dom. 12/216:00 amITO - MDW
2 stops14h 55mSouthwest
Deal found 12/7$869
This Southwest deal was found by Cheapflights users on 12/7. 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. 12/147:55 amMDW - ITO
2 stops17h 45mSouthwest
vie. 12/196:00 amITO - MDW
2 stops14h 55mSouthwest
Deal found 12/7$924
This Delta deal was found by Cheapflights users on 12/8. 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.
jue. 12/186:00 amMDW - ITO
2 stops15h 51mDelta
lun. 12/291:44 pmITO - MDW
2 stops15h 05mDelta
Deal found 12/8$1,252
This Southwest deal was found by Cheapflights users on 12/8. 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.
jue. 12/185:30 amMDW - ITO
2 stops16h 40mSouthwest
mié. 12/316:00 amITO - MDW
2 stops12h 55mSouthwest
Deal found 12/8$1,269
This Delta deal was found by Cheapflights users on 12/8. 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.
vie. 12/196:00 amMDW - ITO
2 stops18h 29mDelta
lun. 12/291:44 pmITO - MDW
2 stops15h 05mDelta
Deal found 12/8$1,359
This Delta deal was found by Cheapflights users on 12/8. 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.
jue. 12/186:00 amMDW - ITO
2 stops15h 51mDelta
dom. 12/281:44 pmITO - MDW
2 stops17h 22mDelta
Deal found 12/8$1,434
This Southwest deal was found by Cheapflights users on 12/8. 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.
jue. 12/187:55 amMDW - ITO
2 stops14h 15mSouthwest
lun. 1/56:55 pmITO - MDW
2 stops13h 40mSouthwest
Deal found 12/8$1,444

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 diciembre 9, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$414
(Delta)

One-way from

$223
(Southwest)

Popular in

December

Cheapest in

September

Average price

$1,118
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. 8% potential increase in price ($66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($36 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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 diciembre 9, 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

mié. 2/25

9:34 am-7:34 pm

2 stops14h 00m

Kona Intl

mar. 3/3

9:45 pm-5:37 pm

2 stops15h 52m

$444

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

mié. 2/4

6:10 am-6:10 pm

2 stops16h 00m

Kona Intl

mar. 2/10

9:25 pm-12:35 pm

1 stop11h 10m

$530

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

mié. 1/21

6:10 am-6:10 pm

2 stops16h 00m

Kona Intl

mié. 1/28

9:25 pm-2:45 pm

2 stops13h 20m

$594

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

lun. 1/5

7:45 am-9:20 pm

2 stops17h 35m

Kona Intl

lun. 1/12

9:25 pm-2:45 pm

2 stops13h 20m

$594

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

mié. 2/25

6:10 am-1:45 pm

1 stop11h 35m

Kona Intl

mié. 3/4

9:25 pm-3:00 pm

1 stop13h 35m

$623

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

jue. 1/22

6:00 am-8:28 pm

2 stops18h 28m

Kona Intl

jue. 1/29

7:55 pm-12:46 pm

2 stops12h 51m

$627

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

mar. 1/13

6:10 am-1:45 pm

1 stop11h 35m

Kona Intl

mar. 1/20

9:25 pm-12:35 pm

1 stop11h 10m

$648

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

mar. 1/20

6:00 am-6:47 pm

2 stops16h 47m

Kona Intl

mar. 1/27

9:30 pm-5:55 pm

2 stops16h 25m

$663

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

mar. 1/20

6:00 am-6:47 pm

2 stops16h 47m

Kona Intl

mar. 2/3

9:55 pm-6:36 pm

2 stops16h 41m

$663

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

mié. 1/14

8:25 am-9:40 pm

2 stops17h 15m

Hilo Intl

jue. 1/22

6:55 pm-12:35 pm

2 stops13h 40m

$664

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/7

Showing 1-10 of 29 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.

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 14h. Fly via Delta or Southwest to get the fastest option. The distance between Chicago Midway Airport and The Big Island 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 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.

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