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$317+ 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KOA
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$539
(Delta)

One-way from

$317
(Delta)

Popular in

December

Cheapest in

September

Average price

$602
Provider with most accurate pricing for Chicago (CHI)-Kona Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Kona Intl flights.
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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 ($24 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 17, 2025.

This Delta deal was found by Cheapflights users on 4/17. 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 9/89:20 amMDW - KOA
2 stops14h 20mDelta
Mon 9/158:40 pmKOA - MDW
2 stops16h 27mDelta
Deal found 4/17$539
This Southwest deal was found by Cheapflights users on 4/16. 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 5/65:35 amMDW - KOA
2 stops17h 35mSouthwest
Tue 5/138:30 pmKOA - MDW
1 stop10h 15mSouthwest
Deal found 4/16$594
This Southwest deal was found by Cheapflights users on 4/16. 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 4/297:30 amMDW - ITO
2 stops15h 40mSouthwest
Thu 5/86:00 amITO - MDW
2 stops12h 20mSouthwest
Deal found 4/16$719
This eDestinos deal was found by Cheapflights users on 4/16. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/58:03 pmMDW - KOA
2 stops22h 52mMultiple Airlines
Tue 5/133:10 pmKOA - MDW
2 stops40h 14mMultiple Airlines
Deal found 4/16$750
This Delta deal was found by Cheapflights users on 4/17. 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.
Tue 5/66:04 amMDW - ITO
2 stops16h 57mDelta
Tue 5/1310:25 amITO - MDW
2 stops17h 15mDelta
Deal found 4/17$894

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 April 17, 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

Mon 5/12

9:20 am-7:10 pm

2 stops14h 50m

Kona Intl

Mon 5/19

8:38 pm-5:45 pm

2 stops16h 07m

$542

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 5/6

5:35 am-6:10 pm

2 stops17h 35m

Kona Intl

Tue 5/13

8:30 pm-11:45 am

1 stop10h 15m

$594

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Tue 4/29

7:30 am-6:10 pm

2 stops15h 40m

Hilo Intl

Thu 5/8

6:00 am-11:20 pm

2 stops12h 20m

$719

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 5/5

8:03 pm-1:55 pm

2 stops22h 52m

Kona Intl

Tue 5/13

3:10 pm-12:24 pm

2 stops40h 14m

$750

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Tue 5/6

6:04 am-6:01 pm

2 stops16h 57m

Hilo Intl

Tue 5/13

10:25 am-8:40 am

2 stops17h 15m

$894

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 6/5

9:20 am-7:10 pm

2 stops14h 50m

$317

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 6/12

5:30 am-12:10 pm

1 stop11h 40m

$452

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sun 6/1

6:00 am-5:01 pm

2 stops16h 01m

$5,145

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

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

Rainfall in The Big Island by month

Plan your trip to The Big Island by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in The Big Island ranges from 1.6 - 2.8 inches per month. January is typically the wettest month, when rainfall can reach 2.8 in. February is typically the driest time to visit The Big Island when rainfall is around 1.6 in.

Temperature in The Big Island by month

Plan your trip to The Big Island by taking into account the average temperature totals by month.

If weather is an important factor for your trip to The Big Island, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 77.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 71.6 F).

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 April 17, 2025.
Peruse reviews from past customers who have flown with Southwest and Delta from Chicago to The Big Island to help guide your decision. 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
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,917 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

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