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Midway

$291+ Cheap flights from The Big Island to Midway (MDW)

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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
KOA — MDW
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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Cheap flight deals from The Big Island to Midway

Keep the following information in mind while searching for The Big Island to Midway flight deals. Data was last updated April 17, 2025.

Round-trip from

$542
(Delta)

One-way from

$291
(Delta)
From The Big Island to Chicago Midway
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One-way flight from The Big Island to Chicago Midway
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Find flight deals from The Big Island to Midway

Cheapest flights from The Big Island to Midway
Explore the most affordable flight options available from The Big Island to Midway. 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 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/208:38 pmKOA - MDW
2 stops16h 07mDelta
Tue 6/39:20 amMDW - KOA
2 stops14h 50mDelta
Deal found 4/16$542
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/88:30 pmKOA - MDW
1 stop13h 05mSouthwest
Wed 5/149:25 pmMDW - KOA
2 stops19h 45mSouthwest
Deal found 4/17$665

Cheapflights Fare Finder

Customize your flight search to find flights from The Big Island to Midway 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 The Big Island to Chicago Midway Airport that are best for you.

Fly from

The Big Island

Fly to

Midway

Route

Depart

Return

Price

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 5/20

8:38 pm-5:45 pm

2 stops16h 07m

Chicago Midway

Tue 6/3

9:20 am-7:10 pm

2 stops14h 50m

$542

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 5/8

8:30 pm-2:35 pm

1 stop13h 05m

Chicago Midway

Wed 5/14

9:25 pm-12:10 pm

2 stops19h 45m

$665

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 6/10

8:35 pm-5:40 pm

2 stops16h 05m

$291

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Tue 6/10

8:20 pm-12:15 pm

1 stop10h 55m

$382

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Best time to book a flight from The Big Island to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from The Big Island 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 The Big Island to Chicago Midway Airport

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated April 17, 2025.
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 The Big Island to Midway. 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 The Big Island to Midway that include hotel bookings?

    Yes. In addition to deals on The Big Island to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from The Big Island to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from The Big Island to Midway.

  • Can I find deals for business class flights from The Big Island to Midway?

    Yes. Cheapflights offers flight deals from The Big Island to Midway 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 The Big Island to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from The Big Island to Chicago Midway Airport (average of $160). Flying from The Big Island to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near The Big Island?

Book flights to The Big Island if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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