MDW - KOA

$408 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 9/5. 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
$554
Southwest
Mon 8/17Wed 8/26
MDW - KOA • 1 stop
Cheapest one-way
$408
Southwest
Sat 9/5
MDW - KOA • 2 stops
Top airlines
Southwest
Cheapest • from $554 (round-trip)
Southwest
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 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

Mon, Aug 17 - Wed, Aug 26
Southwest Logo
6:40 am - 12:40 pm
MDW
-
KOA
11h 00m
1 stop
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$554Southwest
Mon, Apr 20 - Mon, Apr 27
Southwest Logo
5:10 am - 1:15 pm
MDW
-
KOA
13h 05m
1 stop
Southwest Logo
8:25 pm - 2:10 pm
KOA
-
MDW
12h 45m
1 stop
$558Southwest
Mon, Aug 17 - Wed, Aug 26
Southwest Logo
6:40 am - 12:40 pm
MDW
-
KOA
11h 00m
1 stop
Southwest Logo
8:35 pm - 3:15 pm
KOA
-
MDW
13h 40m
2 stops
$560Southwest
Wed, Apr 15 - Wed, Apr 22
Southwest Logo
10:00 am - 6:05 pm
MDW
-
KOA
13h 05m
2 stops
Southwest Logo
8:25 pm - 1:10 pm
KOA
-
MDW
11h 45m
1 stop
$564Southwest
Mon, Apr 20 - Mon, Apr 27
Southwest Logo
5:10 am - 2:30 pm
MDW
-
KOA
14h 20m
2 stops
Southwest Logo
8:25 pm - 2:10 pm
KOA
-
MDW
12h 45m
1 stop
$565Southwest
Fri, May 8 - Thu, May 14
Southwest Logo
10:10 am - 9:25 pm
MDW
-
KOA
16h 15m
2 stops
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$571Southwest
Fri, Apr 24 - Fri, May 1
Southwest Logo
5:10 am - 1:15 pm
MDW
-
KOA
13h 05m
1 stop
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$590Southwest
Tue, Apr 14 - Tue, Apr 28
Southwest Logo
10:00 am - 6:05 pm
MDW
-
KOA
13h 05m
2 stops
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$592Southwest
Fri, May 8 - Thu, May 14
Southwest Logo
10:10 am - 9:25 pm
MDW
-
KOA
16h 15m
2 stops
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$594Southwest
Fri, Apr 24 - Fri, May 1
Southwest Logo
7:50 am - 6:05 pm
MDW
-
KOA
15h 15m
2 stops
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$596Southwest
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 ($554) and Delta ($774).

Find deals

Good to know

Cheapest flight$408
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 $408 for a one-way ticket and $554 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.
8.0
SouthwestOverall score based on 4333 reviews
7.0Food
8.0Comfort
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

10.0 ExcellentGwen, Mar 2026
DAL - BNA
Read more Southwest reviews

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

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)