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$240+ Cheap flights from Kahului (OGG) 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Kahului to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Kahului (OGG) to Midway (MDW). 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 September 15, 2025.

Round-trip from

$813
(Southwest)

One-way from

$240
(Southwest)

Popular in

June

Cheapest in

January

Average price

$466
From Kahului to Chicago Midway
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One-way flight from Kahului to Chicago Midway
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Highest demand for flights based on searches. 26% potential increase in price ($233 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($56 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Kahului to Midway

Cheapest flights from Kahului to Midway
Explore the most affordable flight options available from Kahului to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/14. 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.
Mon 9/158:30 pmOGG - MDW
1 stop10h 45mSouthwest
Mon 9/225:15 amMDW - OGG
1 stop12h 10mSouthwest
Deal found 9/14$759
This Southwest deal was found by Cheapflights users on 9/14. 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 9/188:25 pmOGG - MDW
1 stop10h 20mSouthwest
Thu 9/255:35 amMDW - OGG
1 stop12h 25mSouthwest
Deal found 9/14$769
This Southwest deal was found by Cheapflights users on 9/14. 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.
Fri 12/199:35 pmOGG - MDW
1 stop12h 05mSouthwest
Wed 12/315:25 amMDW - OGG
1 stop11h 40mSouthwest
Deal found 9/14$813
This Southwest deal was found by Cheapflights users on 9/14. 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.
Fri 12/199:35 pmOGG - MDW
1 stop12h 05mSouthwest
Tue 12/305:00 amMDW - OGG
1 stop11h 25mSouthwest
Deal found 9/14$848

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kahului 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 September 15, 2025.
Use the filters below to find and compare flights from Kahului to Chicago Midway Airport that are best for you.

Fly from

Kahului

Fly to

Midway

Route

Depart

Return

Price

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 12/19

9:35 pm-1:40 pm

1 stop12h 05m

Chicago Midway

Wed 12/31

5:25 am-1:05 pm

1 stop11h 40m

$813

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 12/19

9:35 pm-1:40 pm

1 stop12h 05m

Chicago Midway

Tue 12/30

5:00 am-12:25 pm

1 stop11h 25m

$848

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 11/26

8:59 pm-4:39 pm

2 stops15h 40m

Chicago Midway

Sun 11/30

6:00 am-3:28 pm

1 stop13h 28m

$1,078

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 9/30

12:15 pm-8:40 am

2 stops15h 25m

Chicago Midway

Sat 10/4

6:00 am-6:42 pm

2 stops17h 42m

$1,245

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 10/11

11:55 am-8:55 am

2 stops16h 00m

Chicago Midway

Sat 10/18

9:20 am-6:18 pm

2 stops13h 58m

$1,280

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 11/13

9:25 pm-12:30 pm

1 stop11h 05m

$240

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 11/13

1:45 pm-9:01 am

2 stops15h 16m

$245

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 3/13

10:00 am-5:55 am

1 stop14h 55m

$392

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 11/27

5:10 pm-9:51 am

1 stop12h 41m

$512

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 10/30

12:25 pm-8:40 am

2 stops15h 15m

$517

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 12 results
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Best time to book a flight from Kahului to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Kahului 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.

Related info for your journey

Find useful and relevant information for your journey from Kahului to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Kahului to Chicago Midway?

    Most people fly from Kahului (OGG) if they book a flight from Kahului to Chicago Midway. On average, Kahului has 0 outbound flights to Chicago Midway per day from 0 airlines. Kahului is conveniently located just 2.7 mi from Kahului’s city center.

  • How long is the flight from Kahului to Chicago Midway Airport?

    Airlines like Southwest fly from Kahului to Chicago Midway Airport in about 12h 05m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 4184 mi.

  • Can I find deals for flights from Kahului to Midway that include hotel bookings?

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

  • How can I find direct flights from Kahului to Midway?

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

  • Can I find deals for business class flights from Kahului to Midway?

    Yes. Cheapflights offers flight deals from Kahului 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 Kahului to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Kahului to Chicago Midway Airport (average of $160). Flying from Kahului 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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