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$318+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — KOA
Feb 3 — Feb 101
Mon 2/3
Mon 2/10
1 adult, Economy
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Cheap flight deals from Midway to The Big Island

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to The Big Island (zzFUI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$581
(Southwest)

One-way from

$318
(Southwest)

Popular in

December

Cheapest in

September

Average price

$622
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. 4% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 29, 2025.

This Delta deal was found by Cheapflights users on 1/29. 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.
Thu 5/11:16 pmMDW - KOA
2 stops34h 23mDelta
Wed 5/78:40 pmKOA - MDW
2 stops30h 59mDelta
Deal found 1/29$564
This Southwest deal was found by Cheapflights users on 1/28. 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.
Sun 5/46:05 amMDW - KOA
1 stop11h 50mSouthwest
Thu 5/158:30 pmKOA - MDW
1 stop11h 30mSouthwest
Deal found 1/28$576
This Southwest deal was found by Cheapflights users on 1/28. 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.
Sun 2/25:30 amMDW - ITO
2 stops19h 00mSouthwest
Tue 2/116:00 amITO - MDW
2 stops13h 20mSouthwest
Deal found 1/28$729
This eDestinos deal was found by Cheapflights users on 1/29. 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.
Sat 3/156:40 amMDW - KOA
3 stops60h 13mMultiple Airlines
Sat 3/2210:41 amKOA - MDW
2 stops13h 49mMultiple Airlines
Deal found 1/29$1,042
This Delta deal was found by Cheapflights users on 1/29. 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 3/16:00 amMDW - ITO
2 stops15h 24mDelta
Fri 3/71:40 pmITO - MDW
2 stops15h 11mDelta
Deal found 1/29$1,094

Find flights from Midway to The Big Island within your budget

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 January 29, 2025.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 5/7

6:00 am-12:55 pm

1 stop11h 55m

Kona Intl

Thu 5/15

8:30 pm-3:20 pm

2 stops13h 50m

$554

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 3/10

10:25 am-6:55 pm

2 stops13h 30m

Kona Intl

Tue 3/11

9:30 pm-6:02 pm

2 stops15h 32m

$686

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sat 4/12

6:05 am-6:10 pm

2 stops17h 05m

Hilo Intl

Sun 4/20

6:55 pm-12:35 pm

2 stops12h 40m

$764

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sat 3/1

6:00 am-5:24 pm

2 stops15h 24m

Hilo Intl

Fri 3/7

1:40 pm-8:51 am

2 stops15h 11m

$1,094

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 2/5

7:20 am-3:50 pm

1 stop12h 30m

$318

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Wed 2/5

9:40 am-8:35 pm

2 stops14h 55m

$377

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Mon 2/3

6:00 am-5:24 pm

2 stops15h 24m

$457

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Sat 3/29

7:13 pm-7:32 pm

2 stops29h 19m

$504

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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.

Travel insights for flights from Midway to The Big Island

Get recent, data-driven insights about flights from Midway to The Big Island including ideal travel times, pricing trends, and more.

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 January 29, 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
8.1
Very good
4,587 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,587 reviews
Southwest
8.1
Very good
4,587 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,456 reviews
Southwest
8.1
Very good
4,587 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $618). 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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