MDW - KOA
$357 Find Cheap Flights from Chicago Midway Airport to Kailua-Kona - Compare and Save
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 1/31. 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.
Everything you should know
Cheapest round-trip
$527
Typical prices: $663-$889
Southwest
Mon 10/29Mon 11/5
MDW - KOA • 1 stop
Cheapest one-way
$291
Typical prices: $341-$467
Southwest
Wed 1/31
MDW - KOA • 2 stops
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
Thu, Oct 29 - Thu, Nov 5
5:10 am - 12:35 pmMDW Chicago Midway-KOA Kona Intl
12h 25m1 stop Las Vegas Harry Reid Intl
9:30 pm - 11:50 amKOA Kona Intl-MDW Chicago Midway
10h 20m1 stop Las Vegas Harry Reid Intl
$527Southwest
Thu, Oct 29 - Thu, Nov 5
5:10 am - 12:35 pmMDW Chicago Midway-KOA Kona Intl
12h 25m1 stop Las Vegas Harry Reid Intl
11:40 am - 5:45 amKOA Kona Intl-MDW Chicago Midway
14h 05m2 stops Honolulu Sacramento Intl
$536Southwest
Tue, Jan 19 - Wed, Jan 27
7:25 am - 2:55 pmMDW Chicago Midway-KOA Kona Intl
11h 30m1 stop Las Vegas Harry Reid Intl
9:30 pm - 4:25 pmKOA Kona Intl-MDW Chicago Midway
14h 55m1 stop Las Vegas Harry Reid Intl
$570Southwest
Wed, Jan 6 - Thu, Jan 21
7:25 am - 2:55 pmMDW Chicago Midway-KOA Kona Intl
11h 30m1 stop Las Vegas Harry Reid Intl
9:30 pm - 2:55 pmKOA Kona Intl-MDW Chicago Midway
13h 25m2 stops Las Vegas Harry Reid Intl Phoenix Sky Harbor Intl
$576Southwest
Thu, Oct 29 - Thu, Nov 5
9:50 am - 9:30 pmMDW Chicago Midway-KOA Kona Intl
16h 40m2 stops San Jose Honolulu
11:40 am - 5:45 amKOA Kona Intl-MDW Chicago Midway
14h 05m2 stops Honolulu Sacramento Intl
$578Southwest
Tue, Jan 19 - Wed, Jan 27
6:10 am - 2:55 pmMDW Chicago Midway-KOA Kona Intl
12h 45m2 stops Denver Intl Las Vegas Harry Reid Intl
9:30 pm - 2:55 pmKOA Kona Intl-MDW Chicago Midway
13h 25m2 stops Las Vegas Harry Reid Intl Phoenix Sky Harbor Intl
$581Southwest
Tue, Jan 12 - Wed, Jan 20
7:25 am - 2:55 pmMDW Chicago Midway-KOA Kona Intl
11h 30m1 stop Las Vegas Harry Reid Intl
9:30 pm - 12:35 pmKOA Kona Intl-MDW Chicago Midway
11h 05m1 stop Las Vegas Harry Reid Intl
$601Southwest
Tue, Jan 12 - Wed, Jan 20
7:25 am - 2:55 pmMDW Chicago Midway-KOA Kona Intl
11h 30m1 stop Las Vegas Harry Reid Intl
9:30 pm - 2:55 pmKOA Kona Intl-MDW Chicago Midway
13h 25m2 stops Las Vegas Harry Reid Intl Phoenix Sky Harbor Intl
$607Southwest
Thu, Feb 4 - Thu, Feb 11
10:00 am - 9:25 pmMDW Chicago Midway-KOA Kona Intl
15h 25m2 stops Los Angeles Honolulu
9:30 pm - 1:50 pmKOA Kona Intl-MDW Chicago Midway
12h 20m1 stop Las Vegas Harry Reid Intl
$609Southwest
Mon, Nov 9 - Mon, Nov 16
5:45 am - 1:40 pmMDW Chicago Midway-KOA Kona Intl
11h 55m1 stop Las Vegas Harry Reid Intl
9:30 pm - 2:15 pmKOA Kona Intl-MDW Chicago Midway
12h 45m1 stop Las Vegas Harry Reid Intl
$612Southwest
Recent one-way flight deals from Midway to Kailua-Kona
Sun, Jan 31
10:20 am - 9:25 pmMDW Chicago Midway-KOA Kona Intl
15h 05m2 stops Los Angeles Honolulu
$291Southwest
Sun, Jan 31
7:15 am - 2:55 pmMDW Chicago Midway-KOA Kona Intl
11h 40m1 stop Las Vegas Harry Reid Intl
$316Southwest
Sat, Oct 31
6:35 am - 12:35 pmMDW Chicago Midway-KOA Kona Intl
11h 00m1 stop Las Vegas Harry Reid Intl
$357Southwest
Sat, Oct 31
9:29 am - 7:26 pmMDW Chicago Midway-KOA Kona Intl
14h 57m2 stops Detroit Metropolitan Wayne County Los Angeles
$363Delta
Wed, Mar 24
10:15 am - 8:40 pmMDW Chicago Midway-KOA Kona Intl
15h 25m2 stops San Diego Honolulu
$373Southwest
Wed, Nov 11
10:05 am - 9:25 pmMDW Chicago Midway-KOA Kona Intl
15h 20m2 stops Los Angeles Honolulu
$383Southwest
Tue, Dec 15
5:50 am - 2:00 pmMDW Chicago Midway-KOA Kona Intl
12h 10m1 stop Las Vegas Harry Reid Intl
$392Southwest
Tue, Dec 15
5:50 am - 2:00 pmMDW Chicago Midway-KOA Kona Intl
12h 10m1 stop Las Vegas Harry Reid Intl
$423Southwest
Tue, Dec 15
10:05 am - 9:25 pmMDW Chicago Midway-KOA Kona Intl
15h 20m2 stops Los Angeles Honolulu
$429Southwest
Wed, Nov 11
5:50 am - 2:00 pmMDW Chicago Midway-KOA Kona Intl
12h 10m1 stop Las Vegas Harry Reid Intl
$433Southwest
Recent last minute flight deals from Midway to Kailua-Kona
Tue, Oct 6 - Thu, Oct 8
10:15 am - 9:30 pmMDW Chicago Midway-KOA Kona Intl
16h 15m2 stops San Jose Honolulu
10:00 am - 5:50 amKOA Kona Intl-MDW Chicago Midway
14h 50m1 stop Sacramento Intl
$761Southwest
Tue, Oct 6 - Thu, Oct 8
10:15 am - 9:30 pmMDW Chicago Midway-KOA Kona Intl
16h 15m2 stops San Jose Honolulu
11:40 am - 5:55 amKOA Kona Intl-MDW Chicago Midway
13h 15m2 stops Honolulu Oakland
$791Southwest
Tue, Oct 6 - Thu, Oct 8
6:05 am - 12:40 pmMDW Chicago Midway-KOA Kona Intl
11h 35m1 stop Las Vegas Harry Reid Intl
10:00 am - 5:50 amKOA Kona Intl-MDW Chicago Midway
14h 50m1 stop Sacramento Intl
$821Southwest
Booking Insights
Price, demand and travel trends for Chicago Midway Airport to Kailua-Kona flights
Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.
Prices
Airlines
Layovers
How much is a round-trip flight from Chicago Midway Airport to Kailua-Kona?
This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Kailua-Kona departing in october.
Round-trip flights from Chicago Midway Airport to Kailua-Kona typically range from $663 to $889. The lowest price found in the past 5 days was $527, on Southwest.
What is the cheapest layover airport when flying from Chicago Midway Airport to Kailua-Kona?
Flights via Las Vegas Harry Reid Intl (LAS) offer the most affordable fares, with an average round-trip price of $755. Based on KAYAK data over the past 3 months.
When flying from Chicago Midway Airport to Kailua-Kona which airport offers the shortest layover?
Las Vegas Harry Reid Intl (LAS) had the shortest average connection time for Chicago Midway Airport to Kailua-Kona layovers at 6h 32m over the past 3 months.
Key details for Chicago Midway Airport to Kailua-Kona flights
Low season | June |
|---|---|
High season | February |
Cheapest flight | $291 |
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.
Your Chicago Midway Airport to Kailua-Kona flight questions, answered
Find helpful answers about this route, including flight times, airports, airlines and booking tips.
Your guide to booking Chicago Midway Airport to Kailua-Kona flights
Get tips on when to book, when to fly and what to know before your trip.More options for your flight from Midway to Kailua-Kona
Complete your trip to Kailua-Kona with a hotel stay or car rental
Information on your arrival and departure airports
Cabin class types available on flights to Kailua-Kona
Cabin classes available on flights to Kailua-Kona. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Find direct flights to and from Midway and Kailua-Kona
Flights from domestic origins to Kailua-Kona
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.