MDW - OGG

$187 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 2/9. 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, 0 bags

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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$432
Typical prices: $1,032-$1,222
Southwest
Tue 5/12Tue 5/19
MDW - OGG • 2 stops
Cheapest one-way
$187
Multiple Airlines
Mon 2/9
MDW - OGG • 3 stops
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Kahului!
Flight Deals
Booking Insights
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

Tue, May 12 - Tue, May 19
Southwest Logo
7:55 am - 4:05 pmMDW-OGG
13h 10m2 stops
Southwest Logo
8:55 pm - 2:30 pmOGG-MDW
12h 35m1 stop
$432Southwest
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Mon, Feb 23 - Tue, Mar 10
Delta Logo
6:00 am - 3:37 pmMDW-OGG
13h 37m1 stop
Delta Logo
9:09 pm - 5:55 pmOGG-MDW
15h 46m2 stops
$449Delta
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Wed, Jan 7 - Tue, Jan 13
Southwest Logo
5:05 am - 12:50 pmMDW-OGG
11h 45m1 stop
Southwest Logo
9:35 pm - 12:35 pmOGG-MDW
11h 00m1 stop
$451Southwest
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Fri, Jan 9 - Tue, Jan 13
Delta Logo
6:45 am - 3:37 pmMDW-OGG
12h 52m1 stop
Delta Logo
9:05 pm - 5:34 pmOGG-MDW
16h 29m2 stops
$457Delta
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Thu, Jan 1 - Thu, Jan 8
Delta Logo
6:00 am - 3:24 pmMDW-OGG
13h 24m1 stop
Delta Logo
10:00 pm - 4:29 pmOGG-MDW
14h 29m2 stops
$458Delta
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Thu, Jan 15 - Thu, Jan 29
Delta Logo
6:45 am - 3:37 pmMDW-OGG
12h 52m1 stop
Delta Logo
5:10 pm - 9:53 amOGG-MDW
12h 43m1 stop
$461Delta
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Fri, Jan 9 - Tue, Jan 13
Delta Logo
6:45 am - 7:15 pmMDW-OGG
16h 30m2 stops
Delta Logo
9:05 pm - 5:34 pmOGG-MDW
16h 29m2 stops
$463Delta
Find Deal
Thu, Jan 15 - Thu, Jan 22
Delta Logo
6:45 am - 3:37 pmMDW-OGG
12h 52m1 stop
Delta Logo
2:02 pm - 9:08 amOGG-MDW
15h 06m2 stops
$466Delta
Find Deal
Wed, Jan 7 - Tue, Jan 13
Southwest Logo
5:05 am - 12:50 pmMDW-OGG
11h 45m1 stop
Southwest Logo
9:35 pm - 12:35 pmOGG-MDW
11h 00m1 stop
$472Southwest
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Thu, Jan 29 - Sun, Feb 1
Delta Logo
6:00 am - 3:37 pmMDW-OGG
13h 37m1 stop
Delta Logo
10:00 pm - 5:29 pmOGG-MDW
15h 29m2 stops
$478Delta
Find Deal
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.

How much is a round-trip flight from Chicago Midway Airport to Kahului?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Kahului departing in May.
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Good to know

Low seasonAugust
Cheapest flight$187
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 17% 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 $187 for a one-way ticket and $425 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.

  • 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 4252 reviews
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
Airline reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

10.0 ExcellentIlevba, Nov 2025DCA - DAL
Read more Southwest reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

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)