$205 Cheap Flights from Kailua-Kona (KOA) to Chicago (ORD)

View $205 flight on Fri, Sep 19, 2025Opens in a new window

Popular airlines from Kona Intl. Airport (KOA) to Chicago O'Hare Intl. Airport (ORD)

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

Prices were available within the past 7 days and start at $205 for one-way flights and $392 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Hawaiian Airlines
Mon, Oct 27 - Wed, Oct 29
KOA
Kona Coast
ORD
Chicago
$392 Roundtrip, found 6 days ago
$392
Roundtrip
found 6 days ago
Select Hawaiian Airlines flight, departing Mon, Oct 27 from Kona Coast to Chicago, returning Wed, Oct 29, priced at $392 found 6 days ago
Hawaiian Airlines
Tue, Oct 21 - Tue, Oct 28
KOA
Kona Coast
ORD
Chicago
$393 Roundtrip, found 6 days ago
$393
Roundtrip
found 6 days ago
Select Hawaiian Airlines flight, departing Tue, Oct 21 from Kona Coast to Chicago, returning Tue, Oct 28, priced at $393 found 6 days ago
Hawaiian Airlines
Thu, Oct 23 - Tue, Oct 28
KOA
Kona Coast
ORD
Chicago
$404 Roundtrip, found 6 days ago
$404
Roundtrip
found 6 days ago
Select Hawaiian Airlines flight, departing Thu, Oct 23 from Kona Coast to Chicago, returning Tue, Oct 28, priced at $404 found 6 days ago
Alaska Airlines
Wed, Oct 22 - Sun, Oct 26
KOA
Kona Coast
ORD
Chicago
$409 Roundtrip, found 5 days ago
$409
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Wed, Oct 22 from Kona Coast to Chicago, returning Sun, Oct 26, priced at $409 found 5 days ago
United
Fri, Oct 24 - Mon, Oct 27
KOA
Kona Coast
ORD
Chicago
$409 Roundtrip, found 1 hour ago
$409
Roundtrip
found 1 hour ago
Select United flight, departing Fri, Oct 24 from Kona Coast to Chicago, returning Mon, Oct 27, priced at $409 found 1 hour ago
American Airlines
Mon, Nov 17 - Wed, Nov 26
KOA
Kona Coast
ORD
Chicago
$409 Roundtrip, found 21 hours ago
$409
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Mon, Nov 17 from Kona Coast to Chicago, returning Wed, Nov 26, priced at $409 found 21 hours ago
Alaska Airlines
Wed, Oct 22 - Sun, Oct 26
KOA
Kona Coast
ORD
Chicago
$414 Roundtrip, found 5 days ago
$414
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Wed, Oct 22 from Kona Coast to Chicago, returning Sun, Oct 26, priced at $414 found 5 days ago
Southwest Airlines
Wed, Sep 3 - Wed, Sep 10
KOA
Kona Coast
ORD
Chicago
$414 Roundtrip, found 1 hour ago
$414
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Sep 3 from Kona Coast to Chicago, returning Wed, Sep 10, priced at $414 found 1 hour ago
Hawaiian Airlines
Mon, Oct 27 - Thu, Oct 30
KOA
Kona Coast
ORD
Chicago
$416 Roundtrip, found 6 days ago
$416
Roundtrip
found 6 days ago
Select Hawaiian Airlines flight, departing Mon, Oct 27 from Kona Coast to Chicago, returning Thu, Oct 30, priced at $416 found 6 days ago
Alaska Airlines
Sun, Sep 14 - Wed, Sep 17
KOA
Kona Coast
ORD
Chicago
$416 Roundtrip, found 4 days ago
$416
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Sun, Sep 14 from Kona Coast to Chicago, returning Wed, Sep 17, priced at $416 found 4 days ago

Find the cheapest month to fly from Kailua-Kona (KOA) to Chicago (ORD)

September is typically the cheapest month to fly

From $335 - $634 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $873
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $873
Flights from Kailua-Kona (KOA) to Chicago (ORD)
Origin airport
Kona Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, JetBlue Airways, Southwest Airlines, United
Roundtrip price
$391
Distance
4207 mi

Kailua-Kona to Chicago Flights

The cheapest times to fly from Kailua-Kona to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Kailua-Kona to Chicago are during the month of October. You can find some of the cheapest flights from Kailua-Kona to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Kailua-Kona to Chicago

Sunday is one of the best days to book for cheap flights from Kailua-Kona to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Kailua-Kona to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Kailua-Kona to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $205 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Kailua-Kona to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Kailua-Kona to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Kona Intl. Airport (KOA) to O'Hare Intl. Airport (ORD) cost?
Discover the latest flight deals from KOA to ORD by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from KOA to ORD?
The cheapest flights from KOA to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Kona Intl. Airport (KOA) to O'Hare Intl. Airport (ORD)?
Hop on a direct flight with United Airlines and travel straight from Kona Intl. Airport (KOA) to O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from KOA to ORD?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from KOA to ORD. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Kona Intl. Airport (KOA) to O'Hare Intl. Airport (ORD)?
On average, there are 1 direct flights departing from Kona Intl. Airport (KOA) to O'Hare Intl. Airport (ORD) every week. If you can't see one that fits your schedule, consider booking a flight with a layover. Filter your search on Expedia to include one or two stops and choose the next best alternative.
What are the most popular departure times for flights from Kona Intl. Airport (KOA) to O'Hare Intl. Airport (ORD)?
More people fly between KOA and ORD at 6 PM than at any other time. Rather skip the crowds? Travel outside of rush hours and it's possible you'll save on your ticket as well.
What day of the week has the most flights from KOA to ORD?
Saturday has the most flights from Kona Intl. Airport (KOA) to O'Hare Intl. Airport (ORD). Consider leaving on this day and you'll have the best chance of finding a schedule that works for you.
What is the earliest flight from Kona Intl. Airport (KOA) to O'Hare Intl. Airport (ORD)?
Kona Intl. Airport (KOA)'s first flight to O'Hare Intl. Airport (ORD) takes off at approximately 6:00PM UTC-10. With a travel duration of 8h 10m, you'll land at around 6:10AM UTC-6.
How long does it take to fly from Kona Intl. Airport (KOA) to O'Hare Intl. Airport (ORD)?
The average flight duration from KOA to ORD is 8 hours and 10 minutes, covering a total distance of 4,200 mi.
What is the best time to fly from Kona Intl. Airport (KOA) to O'Hare Intl. Airport (ORD)?
To avoid possible delays on the Kona Intl. Airport (KOA) to O'Hare Intl. Airport (ORD) route, aim to travel before 3 PM. Departures after this time have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Kona Intl. Airport (KOA)?
If you're flying on a direct flight from Kona Intl. Airport (KOA) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Kona Intl. Airport (KOA) to O'Hare Intl. Airport (ORD) last-minute?
Holding off until just before your trip to book your flight from KOA to ORD generally means paying more. Although you may find some last-minute deals, they aren't always guaranteed. Keep your travel plans flexible for the best chance of scoring a bargain.
Is it cheaper to book a KOA to ORD flight and hotel package?
Compared with arranging flights and hotels separately, booking a KOA to ORD flight and hotel package with Expedia could lead to significant savings. What's more, having it all in one place will take the stress out of planning your trip. Simply secure your flights and choose from our wide range of hotels, then personalize your trip with extras like tours and car rentals.
Can I cancel or change the date of my flight from Kona Intl. Airport (KOA) to O'Hare Intl. Airport (ORD)?
If you booked your KOA to ORD flight in the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more information.

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Chicago nearby Airports

Chicago

Kailua-Kona to Midway Intl.
$414.00
*Available to One Key members.