MDW - OGG

$268 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 5/26. 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

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$500
Southwest
Wed 8/26Wed 9/2
MDW - OGG • 1 stop
Cheapest one-way
$288
Delta
Tue 5/26
MDW - OGG • 2 stops
Top airlines
Cheapest • from $500 (round-trip)
Best reviews • 8.0 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
Cheapest • Avg $929 (round-trip)
Shortest trip • 11h 48m (one-way)
Insights
Insights
Insights
Insights
Start a new search
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

Wed, Aug 26 - Wed, Sep 2
Southwest Logo
6:50 am - 12:35 pm
MDW
-
OGG
10h 45m
1 stop
Southwest Logo
8:35 pm - 4:15 pm
OGG
-
MDW
14h 40m
2 stops
$500Southwest
Thu, May 28 - Thu, Jun 4
Delta Logo
9:22 am - 7:35 pm
MDW
-
OGG
15h 13m
2 stops
Delta Logo
9:05 pm - 5:56 pm
OGG
-
MDW
15h 51m
2 stops
$521Delta
Wed, Aug 26 - Wed, Sep 2
Southwest Logo
6:50 am - 4:10 pm
MDW
-
OGG
14h 20m
2 stops
Southwest Logo
7:00 pm - 12:05 pm
OGG
-
MDW
12h 05m
2 stops
$526Southwest
Fri, May 29 - Mon, Jun 8
Delta Logo
9:22 am - 7:35 pm
MDW
-
OGG
15h 13m
2 stops
Delta Logo
1:05 pm - 8:37 am
OGG
-
MDW
14h 32m
2 stops
$551Delta
Sun, May 24 - Sun, May 31
Delta Logo
9:23 am - 7:35 pm
MDW
-
OGG
15h 12m
2 stops
Delta Logo
8:00 pm - 6:33 pm
OGG
-
MDW
17h 33m
2 stops
$581Delta
Wed, Sep 30 - Wed, Oct 7
Southwest Logo
6:50 am - 4:10 pm
MDW
-
OGG
14h 20m
2 stops
Southwest Logo
8:35 pm - 2:25 pm
OGG
-
MDW
12h 50m
1 stop
$590Southwest
Thu, May 28 - Tue, Jun 2
Delta Logo
5:10 pm - 10:43 am
MDW
-
OGG
22h 33m
2 stops
Delta Logo
10:00 pm - 5:56 pm
OGG
-
MDW
14h 56m
2 stops
$601Delta
Wed, Jun 3 - Wed, Jun 10
Delta Logo
9:23 am - 7:35 pm
MDW
-
OGG
15h 12m
2 stops
Delta Logo
8:05 pm - 4:16 pm
OGG
-
MDW
15h 11m
2 stops
$603Delta
Wed, Sep 30 - Wed, Oct 7
Southwest Logo
6:50 am - 12:35 pm
MDW
-
OGG
10h 45m
1 stop
Southwest Logo
8:35 pm - 2:25 pm
OGG
-
MDW
12h 50m
1 stop
$605Southwest
Thu, Aug 6 - Wed, Aug 26
Southwest Logo
5:40 am - 12:50 pm
MDW
-
OGG
12h 10m
1 stop
Southwest Logo
8:55 pm - 12:45 pm
OGG
-
MDW
10h 50m
1 stop
$614Southwest
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 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to Kahului were found on Southwest ($500) and Delta ($521).

Good to know

Cheapest flight$288
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 $268 for a one-way ticket and $500 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 4314 reviews
7.0Food
7.5Entertainment
8.1Boarding
8.6Crew
8.0Comfort
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

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

Information on your arrival and departure airports