MDW - KOA

$257 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 9/29. 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

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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Flights 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

Tue, Sep 16 - Mon, Sep 22
Southwest Logo
6:10 am - 12:10 pmMDW-KOA
11h 00m1 stop
Southwest Logo
8:30 pm - 11:45 amKOA-MDW
10h 15m1 stop
$560Southwest
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Tue, Sep 16 - Mon, Sep 22
Southwest Logo
6:10 am - 12:10 pmMDW-KOA
11h 00m1 stop
Southwest Logo
7:00 pm - 1:15 pmKOA-MDW
13h 15m2 stops
$573Southwest
Find Deal
Tue, Sep 16 - Mon, Sep 22
Southwest Logo
6:10 am - 6:10 pmMDW-KOA
17h 00m2 stops
Southwest Logo
7:00 pm - 1:15 pmKOA-MDW
13h 15m2 stops
$610Southwest
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Thu, Sep 11 - Wed, Sep 17
Southwest Logo
5:15 am - 12:10 pmMDW-KOA
11h 55m1 stop
Southwest Logo
8:30 pm - 11:45 amKOA-MDW
10h 15m1 stop
$622Southwest
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Thu, Sep 11 - Wed, Sep 17
Southwest Logo
5:15 am - 1:05 pmMDW-KOA
12h 50m2 stops
Southwest Logo
8:30 pm - 11:45 amKOA-MDW
10h 15m1 stop
$627Southwest
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Tue, Sep 2 - Tue, Sep 9
Delta Logo
6:00 am - 7:00 pmMDW-KOA
18h 00m2 stops
Delta Logo
8:41 pm - 6:37 pmKOA-MDW
16h 56m2 stops
$641Delta
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Tue, Sep 2 - Tue, Sep 9
Delta Logo
6:00 am - 7:00 pmMDW-KOA
18h 00m2 stops
Delta Logo
8:41 pm - 6:37 pmKOA-MDW
16h 56m2 stops
$651Delta
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Wed, Aug 20 - Fri, Aug 29
Southwest Logo
8:40 am - 6:10 pmMDW-KOA
14h 30m2 stops
Southwest Logo
9:15 am - 5:10 amKOA-MDW
14h 55m2 stops
$663Southwest
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Sat, Sep 6 - Mon, Sep 15
Southwest Logo
6:20 am - 12:10 pmMDW-KOA
10h 50m1 stop
Southwest Logo
8:30 pm - 1:55 pmKOA-MDW
12h 25m2 stops
$723Southwest
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Sun, Aug 24 - Fri, Aug 29
Delta Logo
9:15 am - 7:00 pmMDW-KOA
14h 45m2 stops
Delta Logo
8:41 pm - 5:37 pmKOA-MDW
15h 56m2 stops
$724Delta
Find Deal
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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 ($560) and Delta ($641).

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Good to know

Low seasonNovember
High seasonSeptember
Cheapest flight$257
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly and prices are also 25% lower on average.
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 $257 for a one-way ticket and $560 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.

  • Which airline alliances offer flights from Chicago Midway Airport to Kailua-Kona?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Kailua-Kona.

  • 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.

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 4287 reviews
7.1Food
8.2Boarding
7.6Entertainment
8.0Comfort
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

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)

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