KOA - CHI

$197 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 11/13. 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

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
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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

Mon, Nov 24 - Tue, Dec 2
Alaska Airlines Logo
1:40 pm - 7:53 pmKOA-ORD
26h 13m1 stop
Alaska Airlines Logo
8:59 pm - 4:00 pmORD-KOA
23h 01m1 stop
$411Alaska Airlines
Find Deal
Mon, Nov 24 - Tue, Dec 2
Alaska Airlines Logo
7:00 am - 11:32 pmKOA-ORD
12h 32m2 stops
Alaska Airlines Logo
8:59 pm - 4:00 pmORD-KOA
23h 01m1 stop
$473Alaska Airlines
Find Deal
Mon, Nov 24 - Tue, Dec 2
Alaska Airlines Logo
7:00 am - 11:32 pmKOA-ORD
12h 32m2 stops
Alaska Airlines Logo
3:05 pm - 12:55 pmORD-KOA
25h 50m2 stops
$491Alaska Airlines
Find Deal
Tue, Mar 3 - Wed, Mar 4
Alaska Airlines Logo
10:18 am - 5:04 amKOA-ORD
14h 46m2 stops
Alaska Airlines Logo
9:00 am - 6:42 pmORD-KOA
13h 42m2 stops
$502Alaska Airlines
Find Deal
Tue, Mar 3 - Wed, Mar 4
Hawaiian Airlines Logo
8:00 am - 11:59 pmKOA-ORD
11h 59m1 stop
Hawaiian Airlines Logo
2:00 pm - 10:35 pmORD-KOA
12h 35m1 stop
$549Hawaiian Airlines
Find Deal
Wed, Nov 26 - Sun, Nov 30
American Airlines Logo
9:35 pm - 2:13 pmKOA-ORD
12h 38m1 stop
American Airlines Logo
11:42 pm - 4:47 pmORD-KOA
21h 05m1 stop
$573American Airlines
Find Deal
Tue, Apr 7 - Sun, Apr 12
American Airlines Logo
9:31 pm - 12:17 pmKOA-ORD
9h 46m1 stop
American Airlines Logo
6:00 am - 1:33 pmORD-KOA
12h 33m1 stop
$692American Airlines
Find Deal
Wed, Oct 29 - Sun, Nov 2
Delta Logo
8:30 pm - 4:50 pmKOA-ORD
15h 20m2 stops
Delta Logo
7:37 am - 6:30 pmORD-KOA
14h 53m1 stop
$697Delta
Find Deal
Wed, Nov 26 - Sun, Nov 30
Delta Logo
8:30 pm - 1:55 pmKOA-ORD
13h 25m2 stops
Delta Logo
7:47 am - 6:13 pmORD-KOA
14h 26m1 stop
$699Delta
Find Deal
Wed, Nov 26 - Sun, Nov 30
United Airlines Logo
11:55 pm - 4:58 pmKOA-ORD
13h 03m2 stops
United Airlines Logo
11:55 pm - 4:18 pmORD-KOA
20h 23m2 stops
$733United Airlines
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
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 $411 (round-trip)
United Airlines
Best reviews • 7.4 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
October
Cheapest • 36% 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
Cheapest round-trip
$411
Overall average: $945
Alaska Airlines
Mon 11/24Tue 12/2
KOA - ORD • 1 stop
Cheapest one-way
$197
Typical prices: $236-$277
Multiple Airlines
Thu 11/13
KOA - ORD • 1 stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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 $440 on the route between Kailua-Kona (KOA) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

What’s the cheapest day of the week to fly from Kailua-Kona to Chicago?

The average price of all round-trip flights from Kailua-Kona to Chicago clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Chicago on a Monday and more expensive on a Saturday. On your return trip to Kailua-Kona, you should consider flying back on a Tuesday, and avoid Saturdays for better deals.

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 October, where tickets cost $455 (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.

Find deals
Expert advice

Expert advice for your flight from Kailua-Kona to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
KOA

Prepare for USDA checkpoints at KOA; all carry-on baggage will be inspected. Factor this into your travel plans to avoid delays.

Read more about KOAby Blane Bachelor
ORD

Take the CTA Blue Line from ORD to downtown Chicago. It's a 45-minute ride and unaffected by traffic, costing $5 one-way.

Read more about ORDby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD

Stefanie Waldek

Stefanie Waldek

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

Blane Bachelor

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$197
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly and prices are also 9% 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 $197 for a one-way ticket and $411 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.

  • 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 $376 or less one-way.

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.
7.4
United AirlinesOverall score based on 8976 reviews
6.6Food
8.1Crew
7.3Comfort
7.1Entertainment
7.7Boarding
Airline reviews

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

8.0 ExcellentAnonymous, Oct 2025MEM - ORD
Read more United Airlines reviews

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

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

Information on your arrival and departure airports

Kailua-Kona (KOA)

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