MDW - KOA

$569 Find Cheap Flights from Chicago Midway Airport to Kailua-Kona

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Kailua-Kona departing on 10/27. 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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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, Oct 27 - Sat, Nov 1
Southwest Logo
5:40 am - 1:00 pmMDW-KOA
12h 20m1 stop
Southwest Logo
9:15 am - 4:25 amKOA-MDW
14h 10m2 stops
$569Southwest
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Mon, Jan 19 - Thu, Apr 30
Southwest Logo
5:10 am - 1:45 pmMDW-KOA
12h 35m1 stop
Southwest Logo
10:00 am - 5:45 amKOA-MDW
14h 45m1 stop
$572Southwest
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Sat, Nov 8 - Thu, Nov 13
Delta Logo
9:20 am - 7:53 pmMDW-KOA
14h 33m2 stops
Delta Logo
8:30 pm - 6:18 pmKOA-MDW
17h 48m2 stops
$578Delta
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Mon, Jan 19 - Thu, Apr 30
Southwest Logo
8:10 am - 6:10 pmMDW-KOA
14h 00m2 stops
Southwest Logo
8:25 pm - 1:45 pmKOA-MDW
12h 20m2 stops
$599Southwest
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Sat, Oct 25 - Sat, Nov 1
Southwest Logo
6:20 am - 1:00 pmMDW-KOA
11h 40m1 stop
Southwest Logo
9:15 am - 4:25 amKOA-MDW
14h 10m2 stops
$610Southwest
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Sat, Oct 25 - Sat, Nov 1
Southwest Logo
8:30 am - 6:10 pmMDW-KOA
14h 40m2 stops
Southwest Logo
9:15 am - 4:25 amKOA-MDW
14h 10m2 stops
$616Southwest
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Mon, Oct 27 - Sat, Nov 1
Southwest Logo
7:45 am - 6:10 pmMDW-KOA
15h 25m2 stops
Southwest Logo
9:15 am - 4:25 amKOA-MDW
14h 10m2 stops
$618Southwest
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Mon, Oct 27 - Sat, Nov 1
Delta Logo
9:20 am - 7:23 pmMDW-KOA
15h 03m2 stops
Delta Logo
9:30 pm - 5:43 pmKOA-MDW
16h 13m2 stops
$635Delta
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Mon, Oct 27 - Sat, Nov 1
Southwest Logo
5:40 am - 1:00 pmMDW-KOA
12h 20m1 stop
Southwest Logo
7:55 pm - 2:05 pmKOA-MDW
13h 10m1 stop
$640Southwest
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Mon, Oct 27 - Sat, Nov 1
Southwest Logo
5:40 am - 1:00 pmMDW-KOA
12h 20m1 stop
Southwest Logo
9:15 am - 4:25 amKOA-MDW
14h 10m2 stops
$645Southwest
Find Deal
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 ($569) and Delta ($578).

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Good to know

Low seasonNovember
Cheapest flight$569
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 $569 for a round-trip ticket.

  • 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.

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 4242 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
Airline reviews

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

6.0 GoodCarl, Aug 2025MSY - BWI
Read more Southwest reviews

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

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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