MDW - OGG

$247 Find Cheap Flights from Chicago Midway Airport to Kahului - Compare and Save

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 8/18. 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, 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$590
Southwest
Mon 9/14Thu 9/24
MDW - OGG • 1 stop
Cheapest one-way
$247
Southwest
Tue 8/18
MDW - OGG • 1 stop
Top airlines
Southwest
Cheapest • from $590 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Midway and Kahului. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
San Diego (SAN)
Cheapest • Avg $929 (round-trip)
Las Vegas (LAS)
Shortest trip • 11h 30m (one-way)
Insights
Insights
Insights
Insights
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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

Mon, Sep 14 - Thu, Sep 24
Southwest Logo
10:15 am - 4:10 pm
MDW
-
OGG
10h 55m
1 stop
Southwest Logo
7:00 pm - 1:20 pm
OGG
-
MDW
13h 20m
2 stops
$590Southwest
Tue, Oct 13 - Wed, Oct 21
Southwest Logo
6:30 am - 4:10 pm
MDW
-
OGG
14h 40m
2 stops
Southwest Logo
8:35 pm - 1:15 pm
OGG
-
MDW
11h 40m
2 stops
$595Southwest
Thu, Oct 22 - Wed, Oct 28
Southwest Logo
10:00 am - 4:10 pm
MDW
-
OGG
11h 10m
1 stop
Southwest Logo
8:35 pm - 1:15 pm
OGG
-
MDW
11h 40m
1 stop
$596Southwest
Sun, Nov 1 - Tue, Nov 10
Southwest Logo
5:10 am - 12:55 pm
MDW
-
OGG
11h 45m
1 stop
Southwest Logo
9:25 pm - 2:05 pm
OGG
-
MDW
12h 40m
1 stop
$599Southwest
Sun, Aug 23 - Thu, Sep 3
Southwest Logo
6:55 am - 4:10 pm
MDW
-
OGG
14h 15m
2 stops
Southwest Logo
8:55 pm - 12:45 pm
OGG
-
MDW
10h 50m
1 stop
$602Southwest
Tue, Dec 1 - Wed, Dec 9
Southwest Logo
5:45 am - 4:10 pm
MDW
-
OGG
14h 25m
2 stops
Southwest Logo
8:15 pm - 2:55 pm
OGG
-
MDW
14h 40m
1 stop
$605Southwest
Thu, Oct 22 - Wed, Oct 28
Southwest Logo
5:10 am - 1:45 pm
MDW
-
OGG
13h 35m
2 stops
Southwest Logo
8:35 pm - 1:15 pm
OGG
-
MDW
11h 40m
2 stops
$607Southwest
Sat, Nov 14 - Wed, Dec 2
Delta Logo
5:35 pm - 11:53 am
MDW
-
OGG
22h 18m
2 stops
Delta Logo
10:10 pm - 4:50 pm
OGG
-
MDW
14h 40m
2 stops
$608Delta
Tue, Dec 1 - Wed, Dec 9
Southwest Logo
5:45 am - 4:10 pm
MDW
-
OGG
14h 25m
2 stops
Southwest Logo
9:25 pm - 2:55 pm
OGG
-
MDW
13h 30m
2 stops
$610Southwest
Mon, Nov 9 - Wed, Dec 2
Delta Logo
5:35 pm - 11:53 am
MDW
-
OGG
22h 18m
2 stops
Delta Logo
10:10 pm - 4:50 pm
OGG
-
MDW
14h 40m
2 stops
$613Delta
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 provide the cheapest flights from Chicago Midway Airport to Kahului?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from Chicago Midway Airport to Kahului were found on Southwest ($590) and Delta ($608).

Find deals

Good to know

Cheapest flight$247
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 5 days, the lowest price for a flight from Chicago Midway Airport to Kahului was $247 for a one-way ticket and $590 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.
7.9
SouthwestOverall score based on 4239 reviews
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

4.0 OkayJeff, Jun 2026
MCI - FLL
Read more Southwest reviews

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

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)