MDW - KOA

$253 Find Cheap Flights from Chicago Midway Airport to Kailua-Kona

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 Kailua-Kona departing on 9/2. 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 Kailua-Kona

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Kailua-Kona, 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 Kailua-Kona, 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
$505
Southwest
Wed 9/23Wed 9/30
MDW - KOA • 2 stops
Cheapest one-way
$253
Delta
Wed 9/2
MDW - KOA • 2 stops
Top airlines
Southwest
Cheapest • from $505 (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 Kailua-Kona. You'll need at least 1 connection.
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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 Kailua-Kona!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Kailua-Kona (MDW-KOA)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Kailua-Kona 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 Kailua-Kona

Wed, Sep 23 - Wed, Sep 30
Southwest Logo
8:50 pm - 12:40 pm
MDW
-
KOA
20h 50m
2 stops
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$505Southwest
Wed, Sep 23 - Wed, Sep 30
Southwest Logo
8:50 pm - 12:40 pm
MDW
-
KOA
20h 50m
2 stops
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
2 stops
$510Southwest
Wed, Aug 19 - Tue, Aug 25
Southwest Logo
8:50 pm - 12:25 pm
MDW
-
KOA
20h 35m
2 stops
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$535Southwest
Wed, Aug 19 - Tue, Aug 25
Southwest Logo
8:20 pm - 12:25 pm
MDW
-
KOA
21h 05m
2 stops
Southwest Logo
10:00 am - 5:40 am
KOA
-
MDW
14h 40m
2 stops
$540Southwest
Wed, Aug 19 - Tue, Aug 25
Southwest Logo
6:50 am - 12:40 pm
MDW
-
KOA
10h 50m
1 stop
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$544Southwest
Tue, Sep 29 - Fri, Oct 2
Delta Logo
9:20 am - 6:34 pm
MDW
-
KOA
14h 14m
2 stops
Delta Logo
8:40 pm - 6:05 pm
KOA
-
MDW
16h 25m
2 stops
$565Delta
Wed, Sep 23 - Wed, Sep 30
Southwest Logo
6:50 am - 12:40 pm
MDW
-
KOA
10h 50m
1 stop
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$569Southwest
Tue, Oct 20 - Tue, Oct 27
Southwest Logo
8:35 pm - 12:20 pm
MDW
-
KOA
20h 45m
2 stops
Southwest Logo
8:35 pm - 2:10 pm
KOA
-
MDW
12h 35m
2 stops
$570Southwest
Wed, Sep 2 - Wed, Sep 2
Southwest Logo
6:50 am - 12:40 pm
MDW
-
KOA
10h 50m
1 stop
Southwest Logo
8:35 pm - 12:05 pm
KOA
-
MDW
10h 30m
1 stop
$599Southwest
Wed, Sep 2 - Wed, Sep 2
Southwest Logo
6:50 am - 12:40 pm
MDW
-
KOA
10h 50m
1 stop
Southwest Logo
8:35 pm - 4:15 pm
KOA
-
MDW
14h 40m
2 stops
$605Southwest
Booking Insights

KAYAK's insights & trends for Midway to Kailua-Kona flights

Get data-powered insights and trends into flights from Midway to Kailua-Kona 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 Kailua-Kona?

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 Kailua-Kona were found on Southwest ($505) and Delta ($565).

Find deals

Good to know

Cheapest flight$253
Flight from Chicago Midway Airport to Kailua-Kona

When to book flights from Midway to Kailua-Kona

Are your dates flexible? Find out the best times to travel from Midway to Kailua-Kona 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 Kailua-Kona flights

  • What is the cheapest flight from Chicago Midway Airport to Kailua-Kona?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Kailua-Kona was $253 for a one-way ticket and $505 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Kailua-Kona?

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

  • Which aircraft models fly most regularly from Chicago Midway Airport to Kailua-Kona?

    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 Kailua-Kona?

    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 Kailua-Kona.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kailua-Kona 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 Kailua-Kona?

    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 Kailua-Kona with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and KOA 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 Kailua-Kona?

    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 Kailua-Kona 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 Kailua-Kona

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Kailua-Kona. 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 Kailua-Kona? 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 4296 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
7.0Food
8.6Crew
Airline reviews

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

2.0 MediocreAnonymous, May 2026
MCO - MDW
Read more Southwest reviews

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

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.

Everything you need to know for your flight from Midway to Kailua-Kona

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Kailua-Kona (KOA)