MDW - OGG

$191 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 1/19. 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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Everything you should know

Cheapest round-trip
$455
Delta
Thu 1/29Tue 2/3
MDW - OGG • 1 stop
Cheapest one-way
$191
Multiple Airlines
Mon 1/19
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

Thu, Jan 29 - Tue, Feb 3
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m1 stop
Delta Logo
10:00 pm - 6:36 pm
OGG
-
MDW
16h 36m2 stops
$455Delta
Mon, Feb 23 - Thu, Mar 5
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m1 stop
Delta Logo
10:00 pm - 5:45 pm
OGG
-
MDW
15h 45m2 stops
$456Delta
Tue, Jan 27 - Tue, Feb 3
Delta Logo
6:00 am - 7:15 pm
MDW
-
OGG
17h 15m2 stops
Delta Logo
10:00 pm - 6:36 pm
OGG
-
MDW
16h 36m2 stops
$460Delta
Wed, Jan 28 - Wed, Feb 4
Delta Logo
6:00 am - 7:15 pm
MDW
-
OGG
17h 15m2 stops
Delta Logo
10:00 pm - 6:36 pm
OGG
-
MDW
16h 36m2 stops
$461Delta
Thu, Jan 29 - Mon, Feb 2
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m1 stop
Delta Logo
5:10 pm - 9:53 am
OGG
-
MDW
12h 43m1 stop
$467Delta
Thu, Jan 29 - Mon, Feb 9
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m1 stop
Delta Logo
2:02 pm - 8:52 am
OGG
-
MDW
14h 50m2 stops
$473Delta
Tue, Jan 27 - Mon, Feb 2
Delta Logo
6:00 am - 7:15 pm
MDW
-
OGG
17h 15m2 stops
Delta Logo
2:02 pm - 8:52 am
OGG
-
MDW
14h 50m2 stops
$478Delta
Fri, Jan 30 - Tue, Feb 3
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m1 stop
Delta Logo
10:00 pm - 6:36 pm
OGG
-
MDW
16h 36m2 stops
$485Delta
Tue, Jan 20 - Tue, Jan 27
Delta Logo
6:00 am - 7:15 pm
MDW
-
OGG
17h 15m2 stops
Delta Logo
10:00 pm - 5:29 pm
OGG
-
MDW
15h 29m2 stops
$491Delta
Fri, Jan 30 - Thu, Feb 5
Delta Logo
6:00 am - 3:37 pm
MDW
-
OGG
13h 37m1 stop
Delta Logo
5:10 pm - 9:53 am
OGG
-
MDW
12h 43m1 stop
$497Delta
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.

Which airlines fly non-stop between Chicago Midway Airport and Kahului?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Chicago Midway Airport to Kahului.

There is just one airline that flies from Chicago Midway Airport to Kahului direct and that is Southwest. The best round-trip deal found from Southwest for the route is $630.

Find deals

Good to know

Low seasonAugust
Cheapest flight$191
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly and prices are also 21% 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 $190 for a one-way ticket and $455 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 4251 reviews
8.0Comfort
7.0Food
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

2.0 MediocreMatthew, Dec 2025
DCA - OKC
Read more Southwest reviews

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

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

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)