KOA - CHI

$173 Find Cheap Flights from Kailua-Kona to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Kailua-Kona to Chicago departing on 3/3. 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 Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Kailua-Kona to Chicago, 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 Kailua-Kona to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$395
Overall average: $2,912
Multiple Airlines
Thu 4/23Tue 4/28
KOA - ORD • 1 stop
Cheapest one-way
$173
Typical prices: $317-$522
Multiple Airlines
Tue 3/3
KOA - ORD • 3 stops
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
Prepare for USDA checkpoints at Kona Intl.
Take the CTA Blue Line from ORD to downtown Chicago.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Alaska Airlines
Cheapest • from $399 (round-trip)
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
KOA
-
ORD
Cheapest
KOA
-
ORD
Most popular
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 37% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Nonstop flights
1 day a week
There are direct flights from Kailua-Kona to Chicago 1 day a week: Sat.
Direct flights
Direct flights
Direct flights
Direct flights
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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 Chicago!
Flight Deals
Booking Insights
Expert advice
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Kailua-Kona to Chicago 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 Kailua-Kona to Chicago

Thu, Apr 23 - Tue, Apr 28
Multiple Airlines Logo
1:16 pm - 7:03 pm
KOA
-
ORD
24h 47m
1 stop
Multiple Airlines Logo
8:50 am - 10:16 pm
ORD
-
KOA
18h 26m
2 stops
$395Multiple Airlines
Thu, Apr 23 - Tue, Apr 28
Alaska Airlines Logo
1:16 pm - 7:03 pm
KOA
-
ORD
24h 47m
1 stop
Alaska Airlines Logo
8:00 am - 7:52 pm
ORD
-
KOA
16h 52m
1 stop
$399Alaska Airlines
Thu, Apr 23 - Tue, Apr 28
Alaska Airlines Logo
1:16 pm - 7:03 pm
KOA
-
ORD
24h 47m
1 stop
Alaska Airlines Logo
3:52 pm - 2:56 pm
ORD
-
KOA
28h 04m
1 stop
$419Alaska Airlines
Wed, Apr 15 - Mon, Apr 20
Delta Logo
8:50 pm - 4:39 pm
KOA
-
ORD
14h 49m
1 stop
Delta Logo
7:15 am - 7:03 pm
ORD
-
KOA
16h 48m
1 stop
$424Delta
Wed, Apr 15 - Mon, Apr 20
Southwest Logo
8:25 pm - 1:55 pm
KOA
-
ORD
12h 30m
1 stop
Southwest Logo
6:15 am - 2:30 pm
ORD
-
KOA
13h 15m
2 stops
$429Southwest
Thu, Apr 16 - Mon, Apr 20
Delta Logo
10:00 pm - 9:18 pm
KOA
-
ORD
18h 18m
2 stops
Delta Logo
7:15 am - 7:03 pm
ORD
-
KOA
16h 48m
1 stop
$430Delta
Thu, Apr 23 - Tue, Apr 28
Multiple Airlines Logo
7:46 pm - 7:03 pm
KOA
-
ORD
18h 17m
2 stops
Multiple Airlines Logo
6:00 am - 3:21 pm
ORD
-
KOA
14h 21m
2 stops
$433Multiple Airlines
Wed, Apr 15 - Mon, Apr 20
Southwest Logo
8:25 pm - 3:00 pm
KOA
-
ORD
13h 35m
2 stops
Southwest Logo
6:15 am - 2:30 pm
ORD
-
KOA
13h 15m
2 stops
$434Southwest
Thu, Apr 16 - Mon, Apr 20
Delta Logo
10:00 pm - 9:18 pm
KOA
-
ORD
18h 18m
2 stops
Delta Logo
6:25 am - 5:43 pm
ORD
-
KOA
16h 18m
2 stops
$435Delta
Tue, Apr 7 - Sun, Apr 12
Delta Logo
8:55 pm - 1:25 pm
KOA
-
ORD
11h 30m
1 stop
Delta Logo
7:20 am - 2:53 pm
ORD
-
KOA
12h 33m
1 stop
$464Delta
Booking Insights

KAYAK's insights & trends for Kailua-Kona to Chicago flights

Get data-powered insights and trends into flights from Kailua-Kona to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Kailua-Kona to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Kailua-Kona to Chicago costs $334 on the route between Kailua-Kona (KOA) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

What is the cheapest month to fly from Kailua-Kona to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Kailua-Kona to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Kailua-Kona to Chicago is February, where tickets cost $421 (return) on average. On the other hand, the most expensive months are March and May, where the average cost of round-trip tickets is $1,221 and $887 respectively.

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Expert advice

Expert advice for your flight from Kailua-Kona to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Blane Bachelor

Blane Bachelor

Expert on KOA

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more

Good to know

Low seasonJanuary
Cheapest flight$173
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Kailua-Kona to Chicago O'Hare Airport

When to book flights from Kailua-Kona to Chicago

Are your dates flexible? Find out the best times to travel from Kailua-Kona to Chicago 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 flights from Kailua-Kona to Chicago

  • What is the cheapest flight from Kailua-Kona to Chicago?

    In the last 3 days, the lowest price for a flight from Kailua-Kona to Chicago was $173 for a one-way ticket and $395 for a round-trip.

  • Do I need a passport to fly between Kailua-Kona and Chicago?

    A passport is not required to fly from Kailua-Kona to Chicago.

  • Which aircraft models fly most regularly from Kailua-Kona to Chicago?

    The Boeing 787-8 Dreamliner is the aircraft model that flies most regularly on the Kailua-Kona to Chicago flight route.

  • Which airline alliances offer flights from Kailua-Kona to Chicago?

    Star Alliance, and oneworld are the airline alliances operating flights between Kailua-Kona and Chicago, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Kailua-Kona to Chicago?

    You can catch a nonstop flight from Kailua-Kona to Chicago on on Saturday.

  • How does KAYAK find such low prices on flights from Kailua-Kona to Chicago?

    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 Kailua-Kona to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Kailua-Kona to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Kailua-Kona 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 Kailua-Kona to Chicago?

    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 Chicago with an airline and back to Kailua-Kona with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Kailua-Kona to Chicago?

    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 Chicago from Kailua-Kona up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Kailua-Kona to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $360 or less one-way and $778 or less round-trip.

Prefer to fly direct from Kailua-Kona to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Kona Intl to Chicago.
Find which airlines fly direct from Kona Intl Airport to Chicago, which days they fly and book direct flights.

Direct departures

Kona Intl to Chicago

Saturday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago to Kona Intl

Saturday

United Airlines

United Airlines

See more direct flights

Reviews of the top airline flying from Kailua-Kona to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Kailua-Kona to Chicago. 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 Kailua-Kona to Chicago? 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.
7.2
American AirlinesOverall score based on 11262 reviews
8.0Crew
7.2Comfort
6.4Food
7.5Boarding
6.9Entertainment
Airline reviews

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

8.0 ExcellentAnonymous, Feb 2026
SFO - ORD
Read more American Airlines reviews

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

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

Information on your arrival and departure airports

Kailua-Kona (KOA)