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Kahului

$238+ 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OGG
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
1 adult, Economy
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Cheap 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 July 1, 2025.

Round-trip from

$606
(Southwest)

One-way from

$238
(Southwest)

Popular in

November

Cheapest in

August

Average price

$865
From Chicago Midway to Kahului
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One-way flight from Chicago Midway to Kahului
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Highest demand for flights based on searches. 20% potential increase in price ($222 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($73 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 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 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.
Tue 8/266:10 amMDW - OGG
1 stop11h 15mSouthwest
Sun 8/318:30 pmOGG - MDW
1 stop10h 50mSouthwest
Deal found 6/29$622
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/26:00 amMDW - OGG
2 stops18h 13mDelta
Tue 9/912:00 pmOGG - MDW
2 stops15h 35mDelta
Deal found 6/29$645

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 July 1, 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

Tue 8/26

6:10 am-12:25 pm

1 stop11h 15m

Kahului

Sun 8/31

8:30 pm-12:20 pm

1 stop10h 50m

$622

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 9/2

6:00 am-7:13 pm

2 stops18h 13m

Kahului

Tue 9/9

12:00 pm-8:35 am

2 stops15h 35m

$645

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 9/28

8:00 am-6:15 pm

2 stops15h 15m

$238

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 9/2

6:00 am-7:13 pm

2 stops18h 13m

$410

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Kahului

What is the cheapest month to book a flight from Chicago Midway Airport to Kahului?

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Kahului (average of $391). Flying from Chicago Midway Airport to Kahului in June is currently the most expensive (average of $576). 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.

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 July 1, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Kahului, 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
4,273 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.2

Comfort

8.0

Entertainment

7.6

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
4,273 reviews
Southwest
8.0
Very good
4,273 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.2

Comfort

8.0

Entertainment

7.6

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
7,973 reviews
Southwest
8.0
Very good
4,273 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.2

Comfort

8.0

Entertainment

7.6

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 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.

  • What are the cheapest airlines flying from Chicago Midway Airport to Kahului round-trip?

    According to our current data, Southwest ($606), and Delta ($646) offers the cheapest pricing from Chicago Midway Airport to Kahului. Southwest is priced at 30% 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Kahului?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Kahului (average of $391). Flying from Chicago Midway Airport to Kahului in June is currently the most expensive (average of $576). 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
Wailea

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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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$498Average$748FlexibilityNo cancel feeOn-time63%

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