MDW - OGG

$231 Find Cheap Flights from Chicago Midway Airport to Kahului

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Kahului departing on 11/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Kahului

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Kahului, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Kahului, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Midway to Kahului (MDW-OGG)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Kahului that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Kahului

Wed, Oct 22 - Wed, Oct 29
Southwest Logo
6:05 am - 12:25 pmMDW-OGG
11h 20m1 stop
Southwest Logo
8:30 pm - 1:20 pmOGG-MDW
11h 50m1 stop
$491Southwest
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Thu, Oct 30 - Tue, Nov 4
Southwest Logo
7:45 am - 4:30 pmMDW-OGG
13h 45m1 stop
Southwest Logo
9:35 pm - 3:00 pmOGG-MDW
13h 25m2 stops
$497Southwest
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Wed, Dec 3 - Wed, Dec 10
Southwest Logo
5:15 am - 1:10 pmMDW-OGG
11h 55m1 stop
Southwest Logo
9:35 pm - 11:35 amOGG-MDW
10h 00m1 stop
$506Southwest
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Wed, Oct 22 - Wed, Oct 29
Southwest Logo
7:40 am - 4:30 pmMDW-OGG
13h 50m2 stops
Southwest Logo
8:30 pm - 1:20 pmOGG-MDW
11h 50m1 stop
$511Southwest
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Wed, Dec 3 - Wed, Dec 10
Southwest Logo
5:15 am - 2:50 pmMDW-OGG
13h 35m2 stops
Southwest Logo
9:35 pm - 11:35 amOGG-MDW
10h 00m1 stop
$513Southwest
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Wed, Oct 22 - Tue, Oct 28
Southwest Logo
6:25 am - 12:50 pmMDW-OGG
11h 25m1 stop
Southwest Logo
8:30 pm - 12:25 pmOGG-MDW
10h 55m1 stop
$521Southwest
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Tue, Oct 28 - Tue, Nov 4
Southwest Logo
7:40 am - 4:30 pmMDW-OGG
13h 50m2 stops
Southwest Logo
9:35 pm - 11:35 amOGG-MDW
10h 00m1 stop
$527Southwest
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Wed, Dec 3 - Wed, Dec 10
Delta Logo
6:00 am - 7:27 pmMDW-OGG
17h 27m2 stops
Delta Logo
1:45 pm - 8:46 amOGG-MDW
15h 01m2 stops
$532Delta
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Tue, Sep 23 - Mon, Sep 29
Southwest Logo
6:40 am - 1:00 pmMDW-OGG
11h 20m1 stop
Southwest Logo
8:30 pm - 12:15 pmOGG-MDW
10h 45m1 stop
$537Southwest
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Tue, Nov 11 - Mon, Nov 17
Delta Logo
6:00 am - 7:21 pmMDW-OGG
17h 21m2 stops
Delta Logo
10:20 pm - 6:18 pmOGG-MDW
15h 58m2 stops
$624Delta
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Booking Insights

KAYAK's insights & trends for Midway to Kahului flights

Get data-powered insights and trends into flights from Midway to Kahului to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago Midway Airport to Kahului?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Kahului, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Kahului is August, where tickets cost $630 (return) on average. On the other hand, the most expensive months are November and May, where the average cost of round-trip tickets is $1,673 and $1,138 respectively.

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Good to know

Low seasonSeptember
Cheapest flight$231
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Chicago Midway Airport to Kahului

When to book flights from Midway to Kahului

Are your dates flexible? Find out the best times to travel from Midway to Kahului based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Kahului flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Kahului was $231 for a one-way ticket and $491 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Kahului?

    No, a passport isn't needed to fly from Chicago Midway Airport to Kahului. However, local authorities might ask for an official ID.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Kahului?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to Kahului?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Kahului.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Kahului?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Kahului.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Kahului?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kahului from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Kahului?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Kahului with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and OGG can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Kahului?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Kahului from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Midway to Kahului

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Kahului. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Kahului? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4242 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

6.0 GoodCarl, Aug 2025MSY - BWI
Read more Southwest reviews

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

Everything you need to know for your flight from Midway to Kahului

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Kahului (OGG)

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