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$268+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — MDW
feb. 13 — feb. 201
vie. 2/13
vie. 2/20
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 enero 14, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$524
(Southwest)

One-way from

$211
(Southwest)

Popular in

June

Cheapest in

January

Average price

$434
Provider with most accurate pricing for Kahului-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Kahului-Chicago Midway flights.
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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. 15% potential increase in price ($116 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 enero 14, 2026.

This Southwest deal was found by Cheapflights users on 1/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/199:25 pm
OGG
-
MDW
1 stop10h 25m
Southwest
dom. 2/2210:15 pm
MDW
-
OGG
1 stop18h 25m
Southwest
Deal found 1/14$514
This Southwest deal was found by Cheapflights users on 1/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 2/169:35 pm
OGG
-
MDW
1 stop10h 25m
Southwest
mié. 2/185:05 am
MDW
-
OGG
1 stop11h 45m
Southwest
Deal found 1/14$644
This Delta deal was found by Cheapflights users on 1/14. 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.
lun. 2/165:10 pm
OGG
-
MDW
1 stop12h 44m
Delta
mié. 2/186:00 am
MDW
-
OGG
2 stops17h 15m
Delta
Deal found 1/14$747
This Southwest deal was found by Cheapflights users on 1/13. 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.
jue. 3/128:55 pm
OGG
-
MDW
1 stop16h 10m
Southwest
vie. 3/207:15 am
MDW
-
OGG
2 stops13h 40m
Southwest
Deal found 1/13$763
This Southwest deal was found by Cheapflights users on 1/13. 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.
vie. 1/169:35 pm
OGG
-
MDW
1 stop13h 05m
Southwest
dom. 1/185:05 am
MDW
-
OGG
1 stop11h 45m
Southwest
Deal found 1/13$764

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 enero 14, 2026.
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

jue. 2/19

9:25 pm-11:50 am

1 stop10h 25m

Chicago Midway

dom. 2/22

10:15 pm-12:40 pm

1 stop18h 25m

$514

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

lun. 2/16

9:35 pm-12:00 pm

1 stop10h 25m

Chicago Midway

mié. 2/18

5:05 am-12:50 pm

1 stop11h 45m

$644

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

lun. 2/16

5:10 pm-9:54 am

1 stop12h 44m

Chicago Midway

mié. 2/18

6:00 am-7:15 pm

2 stops17h 15m

$747

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

jue. 3/12

8:55 pm-6:05 pm

1 stop16h 10m

Chicago Midway

vie. 3/20

7:15 am-3:55 pm

2 stops13h 40m

$763

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

vie. 2/27

12:59 pm-3:19 pm

3 stops22h 20m

$268

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

sáb. 2/28

12:45 pm-5:05 am

2 stops12h 20m

$270

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

sáb. 2/28

4:12 pm-7:47 pm

3 stops47h 35m

$286

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

sáb. 3/7

4:12 pm-9:45 pm

2 stops49h 33m

$292

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

dom. 3/29

8:55 pm-12:35 pm

1 stop10h 40m

$392

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

vie. 4/3

10:45 am-1:59 pm

2 stops22h 14m

$413

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/13

Showing 1-10 of 14 results
1
2

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 January.
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 and Delta fly from Kahului to Chicago Midway Airport in about 13h 25m. The time it takes to get you to your destination can typically vary by up to 2h 04m. 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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