S$586 Cheap Flights from Chicago to Kailua-Kona

View S$586 flight on Thu, 11 Sep, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Kona Intl. Airport (KOA)

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Cheap Flights from Chicago to Kailua-Kona (MDW-KOA)

Prices were available within the past 7 days and start at S$586 for one-way flights and S$1,273 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 11 Sep - Mon, 15 Sep
MDW
Chicago
KOA
Kona Coast
S$1,273 Return, found 1 day ago
S$1,273
Return
found 1 day ago
Select Delta flight, departing Thu, 11 Sep from Chicago to Kona Coast, returning Mon, 15 Sep, priced at S$1,273 found 1 day ago
Delta
Tue, 29 Jul - Tue, 5 Aug
MDW
Chicago
KOA
Kona Coast
S$1,440 Return, found 1 day ago
S$1,440
Return
found 1 day ago
Select Delta flight, departing Tue, 29 Jul from Chicago to Kona Coast, returning Tue, 5 Aug, priced at S$1,440 found 1 day ago
Delta
Tue, 29 Jul - Tue, 5 Aug
MDW
Chicago
KOA
Kona Coast
S$1,568 Return, found 1 day ago
S$1,568
Return
found 1 day ago
Select Delta flight, departing Tue, 29 Jul from Chicago to Kona Coast, returning Tue, 5 Aug, priced at S$1,568 found 1 day ago
Delta
Sun, 27 Jul - Sun, 3 Aug
MDW
Chicago
KOA
Kona Coast
S$1,602 Return, found 3 days ago
S$1,602
Return
found 3 days ago
Select Delta flight, departing Sun, 27 Jul from Chicago to Kona Coast, returning Sun, 3 Aug, priced at S$1,602 found 3 days ago
Delta
Sun, 27 Jul - Sun, 3 Aug
MDW
Chicago
KOA
Kona Coast
S$1,620 Return, found 3 days ago
S$1,620
Return
found 3 days ago
Select Delta flight, departing Sun, 27 Jul from Chicago to Kona Coast, returning Sun, 3 Aug, priced at S$1,620 found 3 days ago
Delta
Tue, 29 Jul - Tue, 5 Aug
MDW
Chicago
KOA
Kona Coast
S$1,683 Return, found 1 day ago
S$1,683
Return
found 1 day ago
Select Delta flight, departing Tue, 29 Jul from Chicago to Kona Coast, returning Tue, 5 Aug, priced at S$1,683 found 1 day ago
Delta
Sun, 27 Jul - Sun, 3 Aug
MDW
Chicago
KOA
Kona Coast
S$1,988 Return, found 3 days ago
S$1,988
Return
found 3 days ago
Select Delta flight, departing Sun, 27 Jul from Chicago to Kona Coast, returning Sun, 3 Aug, priced at S$1,988 found 3 days ago
Delta
Sun, 27 Jul - Sun, 3 Aug
MDW
Chicago
KOA
Kona Coast
S$2,005 Return, found 3 days ago
S$2,005
Return
found 3 days ago
Select Delta flight, departing Sun, 27 Jul from Chicago to Kona Coast, returning Sun, 3 Aug, priced at S$2,005 found 3 days ago
Delta
Sun, 27 Jul - Sun, 3 Aug
MDW
Chicago
KOA
Kona Coast
S$2,257 Return, found 3 days ago
S$2,257
Return
found 3 days ago
Select Delta flight, departing Sun, 27 Jul from Chicago to Kona Coast, returning Sun, 3 Aug, priced at S$2,257 found 3 days ago
Delta
Sun, 27 Jul - Sun, 3 Aug
MDW
Chicago
KOA
Kona Coast
S$2,643 Return, found 3 days ago
S$2,643
Return
found 3 days ago
Select Delta flight, departing Sun, 27 Jul from Chicago to Kona Coast, returning Sun, 3 Aug, priced at S$2,643 found 3 days ago
Chicago to Kailua-Kona route information
Origin airport
Midway Intl.
Destination airport
Kona Intl.
Airlines serving
Delta
Return price
S$1,272
Distance
6745 km

Perfect flights from Chicago to Kailua-Kona

Your Journey from Chicago to Kailua-Kona

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to Kailua-Kona caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta. Our selection of flights from Midway Intl. to Kona Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Chicago to Kailua-Kona Flights

Experience the joy of finding cheap flights from Midway Intl. to Kona Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$586 and roundtrip prices from S$1,273*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to Kailua-Kona with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Kailua-Kona

Picture yourself stepping off the plane in Kailua-Kona and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Chicago to Kailua-Kona Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Chicago to Kailua-Kona.
 

Beyond the Flight – Exploring Kailua-Kona

With Expedia, your adventure extends beyond the flight. Explore Kailua-Kona at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Chicago to Kailua-Kona with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Chicago to Kailua-Kona with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from MDW to KOA?
The lowest price advertised for a round-trip journey from Midway Airport to Ellison Onizuka Kona Intl. Airport at Keāhole is S$1,273. But you better get a move on. This price is based on fares quoted within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Chicago Airport to Ellison Onizuka Kona Intl. Airport at Keāhole?
Most flights can be cancelled online, but every airline has different terms and conditions. If you do have to cancel your flight, check out our Customer Service Portal and follow the instructions.
How do I find cheap flights from Midway Intl. Airport (MDW) to Ellison Onizuka Kona Intl. Airport at Keāhole that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for Midway Intl. Airport (MDW) to Ellison Onizuka Kona Intl. Airport at Keāhole flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from Midway Intl. Airport (MDW) to Kona Intl. Airport (KOA)?
The distance is around 6,800 kilometres, so fill your carry-on bag with all the things you need to make the long journey comfortable. Wondering what to take on board your Chicago to Kailua-Kona flight? A sleep mask, earplugs and a travel pillow are a few essentials.
Which airlines fly direct from MDW to Kona Intl. Airport (KOA)?
Currently, no airlines offer flights directly from Midway Intl. Airport (MDW) to Ellison Onizuka Kona Intl. Airport at Keāhole. You’ll need to book a flight with at least one stop. To score the best price and connections, lock in your fare well ahead of time.
Are MDW to KOA flight tickets cheaper when they're purchased at the last minute?
Late planners can sometimes find a bargain, with some of the cheapest fares from Midway Intl. Airport (MDW) to Kona Intl. Airport (KOA) showing up a few weeks before the date of departure. If you’d rather book ahead of time, Expedia compares and updates all the best flight deals continually — as early as a year in advance in some cases. It depends on the carrier though, as not all airlines publish prices that far in advance.

Explore a world of travel with Expedia

Chicago Airports

Chicago

O'Hare Intl. to Kailua-Kona
S$595.60
*Available to Expedia members.