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$231+ 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
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
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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 October 16, 2025.

This Delta deal was found by Cheapflights users on 10/16. 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 12/161:55 pmOGG - MDW
2 stops14h 59mDelta
Wed 12/316:00 amMDW - OGG
1 stop13h 24mDelta
Deal found 10/16$466
This Southwest deal was found by Cheapflights users on 10/16. 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.
Wed 11/269:25 pmOGG - MDW
1 stop16h 30mSouthwest
Sun 11/305:35 amMDW - OGG
1 stop11h 50mSouthwest
Deal found 10/16$553
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/41:35 pmOGG - MDW
2 stops15h 05mDelta
Thu 11/136:00 amMDW - OGG
2 stops18h 07mDelta
Deal found 10/14$554
This Delta deal was found by Cheapflights users on 10/16. 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 11/2510:20 pmOGG - MDW
2 stops14h 19mDelta
Sat 11/296:00 amMDW - OGG
1 stop13h 28mDelta
Deal found 10/16$793
This Delta deal was found by Cheapflights users on 10/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3010:05 amOGG - MDW
2 stops18h 40mDelta
Mon 11/36:00 amMDW - OGG
2 stops17h 18mDelta
Deal found 10/14$991

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 October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$537
(Delta)

One-way from

$231
(Delta)

Popular in

June

Cheapest in

January
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
Search Deals
One-way flight from Kahului to Chicago Midway
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($212 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($60 potential savings vs. average RT price).
Search Deals

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 October 16, 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

Tue 12/16

1:55 pm-8:54 am

2 stops14h 59m

Chicago Midway

Wed 12/31

6:00 am-3:24 pm

1 stop13h 24m

$466

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Wed 11/26

9:25 pm-5:55 pm

1 stop16h 30m

Chicago Midway

Sun 11/30

5:35 am-1:25 pm

1 stop11h 50m

$553

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 11/4

1:35 pm-8:40 am

2 stops15h 05m

Chicago Midway

Thu 11/13

6:00 am-8:07 pm

2 stops18h 07m

$554

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 11/25

10:20 pm-4:39 pm

2 stops14h 19m

Chicago Midway

Sat 11/29

6:00 am-3:28 pm

1 stop13h 28m

$793

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 10/30

10:05 am-9:45 am

2 stops18h 40m

Chicago Midway

Mon 11/3

6:00 am-7:18 pm

2 stops17h 18m

$991

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 11/13

5:10 pm-9:52 am

1 stop12h 42m

$231

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 11/7

10:09 pm-5:43 pm

2 stops15h 34m

$237

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sun 11/9

5:10 pm-9:52 am

1 stop12h 42m

$262

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Sun 11/9

3:52 pm-11:38 am

3 stops39h 46m

$301

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Fri 4/10

8:55 pm-12:20 pm

1 stop10h 25m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/15

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 October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Kahului-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 Delta and Southwest fly from Kahului to Chicago Midway Airport in about 14h 59m. The time it takes to get you to your destination can typically vary by up to 1h 31m. Airlines will cover a distance of 4184 mi. This flight may include one or multiple stops.

  • 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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