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Midway

$233+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — MDW
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
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 July 1, 2025.

Round-trip from

$1,407
(Delta)

One-way from

$233
(Southwest)

Popular in

June

Cheapest in

January

Average price

$711
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. 23% potential increase in price ($187 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($33 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 1, 2025.

This Southwest deal was found by Cheapflights users on 6/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/43:45 pmOGG - MDW
2 stops15h 40mSouthwest
Sat 7/196:10 amMDW - OGG
1 stop11h 45mSouthwest
Deal found 6/29$928
This Delta deal was found by Cheapflights users on 6/30. 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.
Wed 7/168:58 pmOGG - MDW
2 stops15h 41mDelta
Mon 7/219:25 amMDW - OGG
2 stops15h 08mDelta
Deal found 6/30$1,407

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 July 1, 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

Wed 7/16

8:58 pm-5:39 pm

2 stops15h 41m

Chicago Midway

Mon 7/21

9:25 am-7:33 pm

2 stops15h 08m

$1,407

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 9/10

8:30 pm-1:25 pm

1 stop11h 55m

$233

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 10/6

9:10 pm-6:07 pm

2 stops15h 57m

$236

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

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.

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 July 1, 2025.
Read through reviews of airlines operating flights from Kahului to Chicago Midway Airport, such as Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,275 reviews

Food

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

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
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

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
7,974 reviews
Southwest
8.0
Very good
4,275 reviews

Food

7.0

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

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 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.

  • 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 Kahului?

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

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