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Kahului

$213+ Cheap flights from Midway (MDW) to Kahului (OGG)

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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OGG
Jan 1 — Jan 81
Thu 1/1
Thu 1/8
1 adult, Economy
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Cheap flight deals from Midway to Kahului

Cheapest flights from Midway to Kahului
Explore the most affordable flight options available from Midway to Kahului. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 2, 2025.

This Southwest deal was found by Cheapflights users on 11/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:00 amMDW - OGG
1 stop11h 25mSouthwest
Mon 1/129:35 pmOGG - MDW
1 stop15h 00mSouthwest
Deal found 11/30$714
This Southwest deal was found by Cheapflights users on 11/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:45 amMDW - OGG
1 stop12h 25mSouthwest
Tue 12/169:25 pmOGG - MDW
1 stop13h 35mSouthwest
Deal found 11/30$738
This Southwest deal was found by Cheapflights users on 11/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/3010:55 pmMDW - OGG
1 stop17h 30mSouthwest
Sun 12/79:35 pmOGG - MDW
1 stop10h 00mSouthwest
Deal found 11/30$763
This Southwest deal was found by Cheapflights users on 12/2. 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 12/305:10 amMDW - OGG
2 stops13h 40mSouthwest
Tue 1/69:35 pmOGG - MDW
1 stop15h 00mSouthwest
Deal found 12/2$765
This Southwest deal was found by Cheapflights users on 12/2. 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 12/77:45 amMDW - OGG
2 stops14h 25mSouthwest
Wed 12/107:00 pmOGG - MDW
2 stops12h 35mSouthwest
Deal found 12/2$774

Find flight deals from Midway to Kahului

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Kahului (OGG). 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 December 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$430
(Delta)

One-way from

$213
(Southwest)

Popular in

November

Cheapest in

August

Average price

$895
Provider with most accurate pricing for Chicago Midway-Kahului flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Kahului flights.
Search Deals
From Chicago Midway to Kahului
Search Deals
One-way flight from Chicago Midway to Kahului
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($244 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($79 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Kahului 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 December 2, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Kahului that are best for you.

Fly from

Midway

Fly to

Kahului

Route

Depart

Return

Price

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 2/2

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Mon 2/9

10:00 pm-6:36 pm

2 stops16h 36m

$430

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 1/14

6:10 am-6:10 pm

2 stops16h 00m

Kahului

Wed 1/21

9:25 pm-1:10 pm

2 stops11h 45m

$432

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 1/12

5:05 am-12:50 pm

1 stop11h 45m

Kahului

Mon 1/19

9:25 pm-1:10 pm

1 stop11h 45m

$433

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 1/21

6:00 am-6:04 pm

2 stops16h 04m

Kahului

Fri 1/30

10:00 pm-3:38 pm

2 stops13h 38m

$434

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sat 1/24

5:35 am-4:35 pm

2 stops15h 00m

Kahului

Thu 1/29

9:35 pm-4:35 pm

1 stop15h 00m

$438

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Fri 2/20

5:00 am-4:25 pm

2 stops15h 25m

Kahului

Thu 2/26

7:00 pm-12:15 pm

2 stops13h 15m

$441

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 1/29

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Thu 2/5

5:10 pm-12:46 pm

2 stops15h 36m

$451

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 3/2

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Mon 3/9

8:30 pm-5:55 pm

2 stops16h 25m

$451

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 1/6

5:05 am-12:50 pm

1 stop11h 45m

Kahului

Tue 1/13

9:25 pm-2:45 pm

1 stop13h 20m

$454

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 2/23

6:00 am-3:37 pm

1 stop13h 37m

Kahului

Tue 3/10

9:09 pm-5:55 pm

2 stops15h 46m

$479

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/1

Showing 1-10 of 20 results
1
2

Compare providers for flights from Midway to Kahului

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Kahului in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Kahului flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Kahului flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Kahului flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Kahului flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Kahului flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Kahului

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

Reviews of airlines servicing Kahului

Get insights into the airlines that provide service to Kahului. 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 Kahului. Reviews last updated December 2, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Kahului, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Related info for your journey

Find useful and relevant information for your journey from Midway to Kahului. 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 into for flights to Kahului from Chicago Midway?

    Most people fly into Kahului (OGG) if they book a flight to Kahului from Chicago Midway. On average, Kahului has 0 inbound flights from Chicago Midway per day from 1 airline. Kahului is conveniently located just 2.7 mi from Kahului’s city center.

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

    For as low as $430, Delta can have you in Kahului from Chicago Midway Airport in 13h 37m. The distance between Chicago Midway Airport and Kahului is about 4184 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Chicago Midway Airport to Kahului round-trip?

    According to our current data, Southwest ($630), offers the cheapest pricing from Chicago Midway Airport to Kahului. Southwest is priced at 29% lower than the current average price of a flight leaving 3 months from now.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Kahului by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Top airline flying from Midway to Kahului

Discover the top airline that operate flights from Midway to Kahului. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$630Average$811FlexibilityNo cancel feeOn-time63%

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