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The Big Island

$307+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KOA
Jul 1 — Jul 81
Tue 7/1
Tue 7/8
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 June 26, 2025.

Round-trip from

$470
(Southwest)

One-way from

$331
(Delta)

Popular in

March

Cheapest in

September

Average price

$822
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. 3% potential increase in price ($24 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 June 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 June 26, 2025.

This Southwest deal was found by Cheapflights users on 6/25. 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 9/176:10 amMDW - KOA
1 stop11h 00mSouthwest
Wed 9/248:30 pmKOA - MDW
2 stops18h 20mSouthwest
Deal found 6/25$470
This Southwest deal was found by Cheapflights users on 6/25. 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 9/96:10 amMDW - ITO
2 stops17h 00mSouthwest
Tue 9/166:55 pmITO - MDW
2 stops13h 20mSouthwest
Deal found 6/25$490
This Delta deal was found by Cheapflights users on 6/24. 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.
Fri 8/299:30 amMDW - KOA
2 stops14h 30mDelta
Mon 9/88:41 pmKOA - MDW
2 stops16h 56mDelta
Deal found 6/24$658
This Delta deal was found by Cheapflights users on 6/25. 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.
Sat 9/276:00 amMDW - ITO
2 stops14h 59mDelta
Mon 9/299:43 amITO - MDW
2 stops27h 24mDelta
Deal found 6/25$873

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 June 26, 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

Wed 9/17

6:10 am-12:10 pm

1 stop11h 00m

Kona Intl

Wed 9/24

8:30 pm-7:50 pm

2 stops18h 20m

$470

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Tue 9/9

6:10 am-6:10 pm

2 stops17h 00m

Hilo Intl

Tue 9/16

6:55 pm-1:15 pm

2 stops13h 20m

$490

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Fri 8/29

9:30 am-7:00 pm

2 stops14h 30m

Kona Intl

Mon 9/8

8:41 pm-6:37 pm

2 stops16h 56m

$658

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sat 9/27

6:00 am-3:59 pm

2 stops14h 59m

Hilo Intl

Mon 9/29

9:43 am-6:07 pm

2 stops27h 24m

$873

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Sat 10/11

6:20 am-1:00 pm

1 stop11h 40m

$307

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Sat 8/30

9:31 am-7:00 pm

2 stops14h 29m

$331

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Tue 7/15

6:00 am-3:55 pm

2 stops14h 55m

$737

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/25

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 June 26, 2025.
Read reviews from past customers who have flown Southwest and Delta 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
4,276 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,276 reviews
Southwest
8.0
Very good
4,276 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,963 reviews
Southwest
8.0
Very good
4,276 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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

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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 June 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$547Average$693FlexibilityNo cancel feeOn-time63%

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