MDW - KOA

$258 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 5/4. 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
$496
Southwest
Tue 4/14Mon 4/20
MDW - KOA • 1 stop
Cheapest one-way
$258
Delta
Mon 5/4
MDW - KOA • 2 stops
Top airlines
Southwest
Cheapest • from $496 (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

Tue, Apr 14 - Mon, Apr 20
Southwest Logo
6:10 am - 1:15 pm
MDW
-
KOA
12h 05m
1 stop
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$496Southwest
Tue, Apr 14 - Mon, Apr 20
Southwest Logo
6:10 am - 1:15 pm
MDW
-
KOA
12h 05m
1 stop
Southwest Logo
10:00 am - 5:00 am
KOA
-
MDW
14h 00m
2 stops
$502Southwest
Tue, Apr 14 - Mon, Apr 20
Southwest Logo
10:00 am - 9:25 pm
MDW
-
KOA
16h 25m
2 stops
Southwest Logo
10:00 am - 5:00 am
KOA
-
MDW
14h 00m
2 stops
$507Southwest
Wed, Apr 15 - Wed, Apr 22
Southwest Logo
6:10 am - 1:15 pm
MDW
-
KOA
12h 05m
1 stop
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$509Southwest
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
$515Southwest
Wed, Apr 15 - Tue, Apr 21
Southwest Logo
6:10 am - 1:15 pm
MDW
-
KOA
12h 05m
1 stop
Southwest Logo
10:00 am - 5:00 am
KOA
-
MDW
14h 00m
2 stops
$531Southwest
Wed, Apr 15 - Tue, Apr 21
Southwest Logo
10:20 am - 9:25 pm
MDW
-
KOA
16h 05m
2 stops
Southwest Logo
10:00 am - 5:00 am
KOA
-
MDW
14h 00m
2 stops
$536Southwest
Tue, Apr 14 - Mon, Apr 20
Southwest Logo
6:10 am - 2:30 pm
MDW
-
KOA
13h 20m
2 stops
Southwest Logo
10:00 am - 5:00 am
KOA
-
MDW
14h 00m
2 stops
$537Southwest
Thu, Mar 12 - Mon, Mar 16
Southwest Logo
5:00 am - 2:30 pm
MDW
-
KOA
14h 30m
2 stops
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$552Southwest
Tue, Apr 21 - Wed, Apr 29
Delta Logo
9:27 am - 5:43 pm
MDW
-
KOA
13h 16m
2 stops
Delta Logo
8:50 pm - 6:36 pm
KOA
-
MDW
16h 46m
2 stops
$557Delta
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 ($496) and Delta ($557).

Good to know

Cheapest flight$258
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 $258 for a one-way ticket and $496 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 4299 reviews
7.0Food
8.6Crew
8.1Boarding
7.5Entertainment
8.0Comfort
Airline reviews

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

4.0 OkayDaniel, Feb 2026
LGB - PHX
Read more Southwest reviews

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

Everything you need to know for your flight from Midway to Kailua-Kona

Information on your arrival and departure airports