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The Big Island

$217+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KOA
nov. 9 — nov. 161
dom. 11/9
dom. 11/16
1 adult, Economy
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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 octubre 10, 2025.

This Delta deal was found by Cheapflights users on 10/8. 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.
mar. 11/49:20 amMDW - KOA
2 stops14h 33mDelta
dom. 11/99:30 pmKOA - MDW
2 stops16h 48mDelta
Deal found 10/8$456
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/49:20 amMDW - KOA
2 stops14h 33mDelta
mar. 11/118:30 pmKOA - MDW
2 stops17h 48mDelta
Deal found 10/7$489
This Delta deal was found by Cheapflights users on 10/9. 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. 11/159:32 amMDW - KOA
2 stops13h 53mDelta
mié. 11/198:30 pmKOA - MDW
2 stops17h 38mDelta
Deal found 10/9$501
This Southwest deal was found by Cheapflights users on 10/8. 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.
mar. 11/45:15 amMDW - KOA
1 stop12h 25mSouthwest
dom. 11/99:15 pmKOA - MDW
2 stops14h 15mSouthwest
Deal found 10/8$524
This Southwest deal was found by Cheapflights users on 10/9. 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. 11/155:15 amMDW - KOA
2 stops16h 55mSouthwest
mié. 11/199:15 pmKOA - MDW
1 stop12h 25mSouthwest
Deal found 10/9$543
This Southwest deal was found by Cheapflights users on 10/7. 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.
mar. 11/45:15 amMDW - KOA
1 stop12h 25mSouthwest
mar. 11/119:15 pmKOA - MDW
1 stop10h 20mSouthwest
Deal found 10/7$556
This Delta deal was found by Cheapflights users on 10/8. 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.
mar. 10/219:20 amMDW - KOA
2 stops15h 03mDelta
mar. 10/289:30 pmKOA - MDW
2 stops15h 13mDelta
Deal found 10/8$566
This Delta deal was found by Cheapflights users on 10/8. 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.
lun. 11/36:00 amMDW - KOA
2 stops17h 53mDelta
dom. 11/99:30 pmKOA - MDW
2 stops16h 48mDelta
Deal found 10/8$580
This Southwest deal was found by Cheapflights users on 10/9. 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. 10/265:15 amMDW - KOA
1 stop12h 15mSouthwest
jue. 10/308:30 pmKOA - MDW
1 stop11h 45mSouthwest
Deal found 10/9$605
This Southwest deal was found by Cheapflights users on 10/7. 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.
mar. 11/48:10 amMDW - ITO
2 stops17h 30mSouthwest
mar. 11/116:55 pmITO - MDW
2 stops14h 45mSouthwest
Deal found 10/7$606
This Southwest deal was found by Cheapflights users on 10/7. 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.
vie. 10/247:45 amMDW - ITO
2 stops15h 25mSouthwest
vie. 10/316:55 pmITO - MDW
2 stops16h 55mSouthwest
Deal found 10/7$691
This Southwest deal was found by Cheapflights users on 10/7. 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.
vie. 10/315:55 amMDW - ITO
2 stops17h 15mSouthwest
lun. 11/36:55 pmITO - MDW
2 stops13h 50mSouthwest
Deal found 10/7$714

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 octubre 10, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$456
(Delta)

One-way from

$229
(Delta)

Popular in

December

Cheapest in

September

Average price

$649
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. 13% potential increase in price ($114 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 octubre 10, 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

mar. 11/4

9:20 am-7:53 pm

2 stops14h 33m

Kona Intl

dom. 11/9

9:30 pm-6:18 pm

2 stops16h 48m

$456

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

mar. 11/4

9:20 am-7:53 pm

2 stops14h 33m

Kona Intl

mar. 11/11

8:30 pm-6:18 pm

2 stops17h 48m

$489

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

sáb. 11/15

9:32 am-7:25 pm

2 stops13h 53m

Kona Intl

mié. 11/19

8:30 pm-6:08 pm

2 stops17h 38m

$501

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

sáb. 11/15

5:15 am-6:10 pm

2 stops16h 55m

Kona Intl

mié. 11/19

9:15 pm-1:40 pm

1 stop12h 25m

$543

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

mar. 11/4

5:15 am-1:40 pm

1 stop12h 25m

Kona Intl

mar. 11/11

9:15 pm-11:35 am

1 stop10h 20m

$556

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

mar. 10/21

9:20 am-7:23 pm

2 stops15h 03m

Kona Intl

mar. 10/28

9:30 pm-5:43 pm

2 stops15h 13m

$566

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

lun. 11/3

6:00 am-7:53 pm

2 stops17h 53m

Kona Intl

dom. 11/9

9:30 pm-6:18 pm

2 stops16h 48m

$580

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

dom. 10/26

5:15 am-12:30 pm

1 stop12h 15m

Kona Intl

jue. 10/30

8:30 pm-1:15 pm

1 stop11h 45m

$605

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

mar. 11/4

8:10 am-9:40 pm

2 stops17h 30m

Hilo Intl

mar. 11/11

6:55 pm-1:40 pm

2 stops14h 45m

$606

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

lun. 11/3

5:15 am-1:40 pm

1 stop12h 25m

Kona Intl

dom. 11/9

9:15 pm-3:30 pm

2 stops14h 15m

$632

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

Showing 1-10 of 30 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 33m. 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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