MDW - KOA

$248 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 3/10. 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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Everything you should know

Cheapest round-trip
$457
Delta
Mon 2/23Mon 3/2
MDW - KOA • 2 stops
Cheapest one-way
$248
Delta
Tue 3/10
MDW - KOA • 2 stops
Top airlines
Delta
Cheapest • from $457 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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, Feb 23 - Mon, Mar 2
Delta Logo
9:34 am - 7:39 pm
MDW
-
KOA
14h 05m
2 stops
Delta Logo
9:55 pm - 5:37 pm
KOA
-
MDW
15h 42m
2 stops
$457Delta
Mon, Feb 23 - Mon, Mar 2
Southwest Logo
8:10 am - 9:20 pm
MDW
-
KOA
17h 10m
2 stops
Southwest Logo
9:25 pm - 12:35 pm
KOA
-
MDW
11h 10m
1 stop
$461Southwest
Thu, Feb 26 - Fri, Mar 6
Southwest Logo
7:55 am - 6:10 pm
MDW
-
KOA
14h 15m
2 stops
Southwest Logo
12:35 pm - 5:55 am
KOA
-
MDW
13h 20m
2 stops
$466Southwest
Thu, Feb 26 - Fri, Mar 6
Southwest Logo
5:00 am - 1:45 pm
MDW
-
KOA
12h 45m
1 stop
Southwest Logo
12:35 pm - 5:55 am
KOA
-
MDW
13h 20m
2 stops
$487Southwest
Tue, Feb 24 - Sun, Mar 1
Delta Logo
9:34 am - 7:39 pm
MDW
-
KOA
14h 05m
2 stops
Delta Logo
10:55 pm - 6:40 pm
KOA
-
MDW
15h 45m
2 stops
$517Delta
Fri, Feb 27 - Sat, Mar 7
Southwest Logo
5:00 am - 1:45 pm
MDW
-
KOA
12h 45m
1 stop
Southwest Logo
7:05 am - 12:10 am
KOA
-
MDW
13h 05m
2 stops
$534Southwest
Fri, Feb 27 - Sat, Mar 7
Southwest Logo
7:45 am - 6:10 pm
MDW
-
KOA
14h 25m
2 stops
Southwest Logo
7:05 am - 12:10 am
KOA
-
MDW
13h 05m
2 stops
$539Southwest
Thu, Feb 19 - Wed, Feb 25
Southwest Logo
7:55 am - 6:10 pm
MDW
-
KOA
14h 15m
2 stops
Southwest Logo
9:25 pm - 3:00 pm
KOA
-
MDW
13h 35m
1 stop
$554Southwest
Thu, Feb 19 - Wed, Feb 25
Southwest Logo
7:55 am - 6:10 pm
MDW
-
KOA
14h 15m
2 stops
Southwest Logo
9:25 pm - 3:05 pm
KOA
-
MDW
13h 40m
2 stops
$559Southwest
Wed, Apr 1 - Tue, Apr 7
Southwest Logo
6:30 am - 6:05 pm
MDW
-
KOA
16h 35m
2 stops
Southwest Logo
8:25 pm - 2:10 pm
KOA
-
MDW
12h 45m
1 stop
$567Southwest
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 Delta ($457) and Southwest ($461).

Find deals

Good to know

Cheapest flight$248
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 $248 for a one-way ticket and $457 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 4269 reviews
7.5Entertainment
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

Great vacation. Can't wait till next year for another one.

10.0 ExcellentJohn, Jan 2026
SAT - PHX
Read more Southwest reviews

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

The flight crew was extremely rude and especially not helpful when our flight was delayed.

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)