MDW - KOA

$259 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 3/17. 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
$503
Delta
Tue 3/3Mon 3/9
MDW - KOA • 2 stops
Cheapest one-way
$259
Multiple Airlines
Tue 3/17
MDW - KOA • 3 stops
Start a new search
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
Useful Info
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

Tue, Mar 3 - Mon, Mar 9
Delta Logo
9:34 am - 7:39 pm
MDW
-
KOA
14h 05m
2 stops
Delta Logo
9:55 pm - 5:54 pm
KOA
-
MDW
14h 59m
2 stops
$503Delta
Wed, Apr 15 - Wed, Apr 22
Southwest Logo
10:20 am - 9:25 pm
MDW
-
KOA
16h 05m
2 stops
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$510Southwest
Mon, Apr 13 - Thu, Apr 23
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
$512Southwest
Sat, Feb 7 - Wed, Feb 18
Delta Logo
1:26 pm - 6:30 pm
MDW
-
KOA
33h 04m
2 stops
Delta Logo
10:55 pm - 5:37 pm
KOA
-
MDW
14h 42m
2 stops
$516Delta
Mon, Apr 13 - Thu, Apr 23
Southwest Logo
5:10 am - 2:15 pm
MDW
-
KOA
14h 05m
2 stops
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$518Southwest
Tue, Mar 3 - Mon, Mar 9
Southwest Logo
6:10 am - 1:45 pm
MDW
-
KOA
11h 35m
1 stop
Southwest Logo
8:25 pm - 11:55 am
KOA
-
MDW
10h 30m
1 stop
$532Southwest
Wed, Apr 15 - Wed, Apr 22
Delta Logo
9:27 am - 6:55 pm
MDW
-
KOA
14h 28m
2 stops
Delta Logo
8:55 pm - 5:54 pm
KOA
-
MDW
15h 59m
2 stops
$535Delta
Tue, Mar 3 - Mon, Mar 9
Southwest Logo
6:10 am - 6:10 pm
MDW
-
KOA
16h 00m
2 stops
Southwest Logo
8:25 pm - 11:55 am
KOA
-
MDW
10h 30m
1 stop
$538Southwest
Tue, Apr 7 - Mon, Apr 13
Southwest Logo
6:10 am - 1:15 pm
MDW
-
KOA
12h 05m
1 stop
Southwest Logo
8:25 pm - 2:10 pm
KOA
-
MDW
12h 45m
1 stop
$582Southwest
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
$587Delta
Useful Info

Good to know

Cheapest flight$259
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 $259 for a one-way ticket and $428 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 4260 reviews
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

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

10.0 ExcellentJohn, Jan 2026
BWI - MDW
Read more Southwest reviews

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.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

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)