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$327+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — MDW
Jan 8 — Jan 151
Thu 1/8
Thu 1/15
1 adult, Economy
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Cheap 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 December 9, 2025.

This Southwest deal was found by Cheapflights users on 12/8. 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 12/289:35 pmOGG - MDW
1 stop10h 40mSouthwest
Wed 12/315:15 amMDW - OGG
2 stops13h 35mSouthwest
Deal found 12/8$765
This Southwest deal was found by Cheapflights users on 12/8. 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 12/159:25 pmOGG - MDW
1 stop13h 35mSouthwest
Thu 12/185:30 amMDW - OGG
1 stop11h 35mSouthwest
Deal found 12/8$838
This Southwest deal was found by Cheapflights users on 12/9. 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 12/259:35 pmOGG - MDW
1 stop14h 05mSouthwest
Sun 12/285:40 amMDW - OGG
1 stop11h 45mSouthwest
Deal found 12/9$993
This Delta deal was found by Cheapflights users on 12/8. 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.
Mon 12/1510:00 pmOGG - MDW
2 stops16h 18mDelta
Thu 12/189:59 amMDW - OGG
2 stops15h 43mDelta
Deal found 12/8$1,046
This Delta deal was found by Cheapflights users on 12/9. 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 12/245:05 pmOGG - MDW
1 stop12h 00mDelta
Sun 12/286:00 amMDW - OGG
1 stop13h 24mDelta
Deal found 12/9$1,419

Find 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 December 9, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$765
(Southwest)

One-way from

$327
(Southwest)
Provider with most accurate pricing for Kahului-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Kahului-Chicago Midway flights.
Search Deals
From Kahului to Chicago Midway
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One-way flight from Kahului to Chicago Midway
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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 December 9, 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

Sun 12/28

9:35 pm-12:15 pm

1 stop10h 40m

Chicago Midway

Wed 12/31

5:15 am-2:50 pm

2 stops13h 35m

$765

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 12/25

9:35 pm-3:40 pm

1 stop14h 05m

Chicago Midway

Sun 12/28

5:40 am-1:25 pm

1 stop11h 45m

$993

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 12/24

5:05 pm-9:05 am

1 stop12h 00m

Chicago Midway

Sun 12/28

6:00 am-3:24 pm

1 stop13h 24m

$1,419

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Mon 5/18

10:00 am-6:00 am

1 stop15h 00m

$327

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sun 4/12

8:31 am-1:59 pm

3 stops24h 28m

$401

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 2/7

9:35 pm-3:25 pm

2 stops13h 50m

$417

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 4/4

8:56 pm-1:59 pm

3 stops36h 03m

$586

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 1/13

10:00 pm-4:29 pm

2 stops14h 29m

$612

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sat 4/4

12:55 pm-5:55 am

1 stop12h 00m

$804

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 1/14

10:00 pm-6:32 pm

2 stops16h 32m

$906

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

Showing 1-10 of 11 results
1
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Compare providers for flights from Kahului to Midway

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 Kahului to Midway 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 Kahului-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Kahului-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Kahului-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Kahului-Chicago Midway Airport 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 Kahului-Chicago Midway Airport 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 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 10h 40m. 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.

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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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