KOA - CHI

$221 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 12/24. 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
0 bags

Search 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
In the last 7 days travelers have searched 47,107,125 times on KAYAK, and here is why:

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Cheap Flight Deals from Kailua-Kona to Chicago (KOA-CHI)

 
These are the cheapest deals for flights from Kailua-Kona to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Kailua-Kona to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Kailua-Kona to Chicago.

Recent one-way flight deals from Kailua-Kona to Chicago

Only flying one-way? Below are some of the best one-way flight deals from Kailua-Kona to Chicago found on KAYAK recently.

Recent last minute flight deals from Kailua-Kona to Chicago

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Kailua-Kona to Chicago.

Recent direct flight deals from Kailua-Kona to Chicago

The latest deals for direct flights from Kailua-Kona to Chicago so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Kailua-Kona to Chicago

Find recent round-trip train or bus tickets from Kailua-Kona to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
9:20 pm - 11:47 pmKOA-ORD
22h 27m1 stop
6:55 pm - 11:44 pmORD-KOA
32h 49m1 stop
$576Alaska Airlines
Find Deal
Fri, Dec 6 - Sat, Jan 11
8:05 pm - 3:50 pmKOA-ORD
15h 45m2 stops
6:55 pm - 11:44 pmORD-KOA
32h 49m1 stop
$582Alaska Airlines
Find Deal
Fri, Dec 6 - Sat, Jan 11
6:10 am - 11:20 pmKOA-MDW
13h 10m2 stops
7:20 am - 3:50 pmMDW-KOA
12h 30m1 stop
$635Southwest
Find Deal
Wed, Jan 8 - Wed, Jan 22
6:10 am - 11:20 pmKOA-MDW
13h 10m2 stops
8:35 pm - 3:50 pmMDW-KOA
23h 15m2 stops
$640Southwest
Find Deal
Wed, Jan 8 - Wed, Jan 22
1:15 pm - 12:46 pmKOA-MDW
19h 31m2 stops
5:07 pm - 6:10 pmMDW-KOA
29h 03m2 stops
$692Delta
Find Deal
Wed, Jan 8 - Tue, Jan 21
10:30 pm - 5:47 pmKOA-MDW
15h 17m2 stops
6:00 am - 8:55 pmMDW-KOA
18h 55m2 stops
$735Delta
Find Deal
Thu, Jan 9 - Thu, Jan 23
9:40 pm - 2:11 pmKOA-ORD
12h 31m1 stop
6:00 am - 6:34 pmORD-KOA
16h 34m1 stop
$823American Airlines
Find Deal
Wed, Dec 18 - Wed, Dec 25
3:03 pm - 5:12 amKOA-ORD
10h 09m1 stop
8:30 pm - 3:57 pmORD-KOA
23h 27m1 stop
$832American Airlines
Find Deal
Fri, Dec 20 - Sat, Dec 28
2:20 pm - 5:01 amKOA-ORD
10h 41m1 stop
11:15 am - 4:30 pmORD-KOA
9h 15mnonstop
$983United Airlines
Find Deal
Fri, Dec 6 - Sat, Jan 11
8:55 pm - 11:25 amKOA-ORD
10h 30m1 stop
9:20 am - 2:38 pmORD-KOA
9h 18mnonstop
$1,358United Airlines
Find Deal
Fri, Dec 20 - Sat, Dec 28
9:45 pm - 2:11 pmKOA-ORD
12h 26m1 stop
$221American Airlines
Find Deal
Tue, Dec 24
3:03 pm - 8:25 amKOA-ORD
13h 22m2 stops
$226American Airlines
Find Deal
Tue, Dec 24
11:17 am - 4:58 pmKOA-ORD
24h 41m2 stops
$257Alaska Airlines
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Mon, Mar 17
11:15 pm - 11:59 pmKOA-ORD
20h 44m1 stop
$267Alaska Airlines
Find Deal
Sun, Jan 26
10:30 pm - 6:14 pmKOA-MDW
15h 44m2 stops
$316Delta
Find Deal
Wed, Jan 8
9:30 pm - 6:05 pmKOA-ORD
16h 35m2 stops
$326Delta
Find Deal
Fri, Dec 20
6:10 am - 10:40 pmKOA-MDW
12h 30m2 stops
$351Southwest
Find Deal
Sat, Feb 8
8:30 pm - 2:00 pmKOA-ORD
12h 30m2 stops
$381Southwest
Find Deal
Sat, May 10
11:43 pm - 2:44 pmKOA-ORD
11h 01m1 stop
$534United Airlines
Find Deal
Wed, Jan 1
6:00 pm - 6:10 amKOA-ORD
8h 10mnonstop
$557United Airlines
Find Deal
Sat, Feb 8
9:45 pm - 12:16 pmKOA-ORD
10h 31m1 stop
6:50 pm - 3:36 pmORD-KOA
24h 46m1 stop
$760American Airlines
Find Deal
Thu, Nov 21 - Fri, Nov 29
4:35 pm - 9:25 amKOA-ORD
12h 50m2 stops
5:02 pm - 3:36 pmORD-KOA
26h 34m1 stop
$765American Airlines
Find Deal
Thu, Nov 21 - Fri, Nov 29
9:25 pm - 5:02 pmKOA-MDW
15h 37m2 stops
9:31 am - 7:53 pmMDW-KOA
14h 22m2 stops
$797Delta
Find Deal
Thu, Nov 21 - Fri, Nov 29
9:00 pm - 5:09 pmKOA-ORD
16h 09m2 stops
7:05 am - 7:53 pmORD-KOA
16h 48m2 stops
$797Delta
Find Deal
Thu, Nov 21 - Fri, Nov 29

Flights from Kailua-Kona to Chicago - Travel Insights & Trends

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Kailua-Kona to Chicago.
Our data shows that the cheapest route for a one-way flight from Kailua-Kona to Chicago cost $347 and was between Kailua-Kona and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $685.

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

The average price of all flights from Kailua-Kona to Chicago clicked on KAYAK for each day over the last 12 months.
For Kailua-Kona to Chicago, Tuesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago back to Kailua-Kona, the best deals are generally found on Tuesday, with Saturday being the most expensive.

Good to know

Low season

August

High season

February

Cheapest flight

$221
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 14% 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

  • How many flights are there between Kailua-Kona and Chicago per day?

    There is a maximum of 1 nonstop flight a day that takes off from Kailua-Kona and lands in Chicago, with an average flight time of 8h 10m. The most common departure time is 6:00 pm and most flights take off in the evening. Each week, there are 1 flights.

  • 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 $221 for a one-way ticket and $576 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 is the only airline alliance operating flights between Kailua-Kona and Chicago.

  • 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.

  • Which is the best airline for flights from Kailua-Kona to Chicago, Alaska Airlines or United Airlines?

    The two airlines most popular with KAYAK users for flights from Kailua-Kona to Chicago are Alaska Airlines and United Airlines. With an average price for the route of $462 and an overall rating of 8.0, Alaska Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $577 and an overall rating of 7.4.

  • 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.

See more FAQs

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 $514 or less one-way.

Prefer to fly non-stop from Kailua-Kona to Chicago?

Find which airlines fly direct from Kona Intl Airport to Chicago, which days they fly and book direct flights.

Nonstop departures

Kona Intl to Chicago

Saturday

Lufthansa, United Airlines

Lufthansa, United Airlines

See more direct flights

Nonstop returns

Chicago to Kona Intl

Saturday

United Airlines

United Airlines

See more direct flights
See more direct flights

Top 3 airlines serving 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.
8.0
Alaska AirlinesOverall score based on 9460 reviews
7.9Comfort
7.1Entertainment
8.5Crew
7.2Food
8.2Boarding
Airline reviews

The airline was great. What was annoying as hell were the inaccurate emails from KAYAK telling me the boarding gate changed and the date of my flight was 1 day later then the actual flight 😡

8.0 ExcellentTerry, Nov 2024PDX - ORD
Read more Alaska Airlines reviews

The airline was great. What was annoying as hell were the inaccurate emails from KAYAK telling me the boarding gate changed and the date of my flight was 1 day later then the actual flight 😡

Paid additional for seat upgrade, but got same seat as no upgrade.

We're an hour late to leave airport due to not enough crew to load baggage onto the aircraft. Missed my connecting flight. The customer service was helpful, but the second plane was also late to depart and was very hot inside. Not a great experience, but the crew did the best they could.

As expected cyst service up front was very good we needed assistance at the gates and they were very accommodating

Always delayed, inadequate availability of room for baggage but the crew were good & approachable.

I had wonderful flight. Only negative was the entertainment. Because there was not any entertainment on the plane.

It would have been perfect if it had not been the fact that departure was delayed.

No food, no entertainment, three and three seating is the worst. Aisle is too narrow and probably a safety violation but no problem in the aircraft industry. Crew was good and pleasant. Ground crew was bad. Previous passenger’s rubbish was not picked up. Of course the seats we’re cleaned either.

On time flights, their system for pre-registering what food you want is buggy and missed our food order twice.

Smoothest landing ever, great flight. No window was a bummer, I checked seat guru but it didn’t say anything about 11a not having a window, but my wife and I had all three seats to ourselves and it was a night flight so no big deal.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

I was pleased and I had a very good experience. The staff was friendly and attentive.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

The staff was very friendly. The seats seemed quite small. Overall the flight was pleasant.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

Charging and entertainment didn't work. The meal was horrible. They only came by with the drink cart one time for the 8 hour flight. They did come by with water a couple times.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.

The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.

Airplane was cold. Flight attendants were rude. Phone charger did not work. No food available.

3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed

My initial flight to ORD was extended without reason. We circled the airport a few time and then drove on the ground for at least 20 minutes. These kinds of delays are annoying but somewhat expected… it would be nice if the crew would make an announcement to give updates on how long we could expect to be delayed.

The flight was uneventful. What was a problem was I was delayed getting home one entire day because the flight from Sacramento was delayed. That made getting to my connecting flight impossible. I had to stay another night at the hotel and incur that expense as a result.

This flight was fine but had no time to breathe as the connection was late from Sea to ORD.. Super stressful. If we checked bags, the trip would have been very distressed.

Seats were very uncomfortable. I paid extra for a seat with more leg room, the seat was no different than a seat at the back of the plane. Flight attendant was rude.

the food choice of packaged chips and popcorn was utterly ridiculous for first class

Book cheap flights from Kailua-Kona to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Kailua-Kona to Chicago found on KAYAK in the last 72 hours.
12/24Tue
1 stopAmerican Airlines
12h 26mKOA-ORD
$221
12/24Tue
2 stopsAmerican Airlines
13h 22mKOA-ORD
$226
3/17Mon
2 stopsAlaska Airlines
24h 41mKOA-ORD
$257
1/26Sun
1 stopAlaska Airlines
20h 44mKOA-ORD
$267
1/8Wed
2 stopsDelta
15h 44mKOA-MDW
$316
12/20Fri
2 stopsDelta
16h 35mKOA-ORD
$326
2/8Sat
2 stopsSouthwest
12h 30mKOA-MDW
$351
5/10Sat
2 stopsSouthwest
12h 30mKOA-ORD
$381
1/1Wed
1 stopUnited Airlines
11h 01mKOA-ORD
$534
2/8Sat
nonstopUnited Airlines
8h 10mKOA-ORD
$557

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Last minute flights from Kailua-Kona to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Kailua-Kona to Chicago that are departing in the next 10 days.
11/21Thu
multi-stopAmerican Airlines
10h 31mKOA-ORD
11/29Fri
multi-stopAmerican Airlines
24h 46mORD-KOA
$760
11/21Thu
multi-stopAmerican Airlines
12h 50mKOA-ORD
11/29Fri
multi-stopAmerican Airlines
26h 34mORD-KOA
$765
11/21Thu
multi-stopDelta
15h 37mKOA-MDW
11/29Fri
multi-stopDelta
14h 22mMDW-KOA
$797
11/21Thu
multi-stopDelta
16h 09mKOA-ORD
11/29Fri
multi-stopDelta
16h 48mORD-KOA
$797

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

Information on your arrival and departure airports

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