KOA - CHI

$268 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 3/10. 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.
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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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Cheap Flight Deals 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.

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.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
8:30 pm - 1:31 pmKOA-ORD
12h 01m1 stop
7:30 am - 5:42 pmORD-KOA
15h 12m1 stop
$435Delta
Find Deal
Tue, Apr 22 - Wed, Apr 30
8:30 pm - 1:31 pmKOA-ORD
12h 01m1 stop
6:40 am - 6:39 pmORD-KOA
16h 59m2 stops
$461Delta
Find Deal
Tue, Apr 22 - Wed, Apr 30
1:37 pm - 5:53 amKOA-ORD
11h 16m1 stop
5:38 pm - 12:07 pmORD-KOA
23h 29m1 stop
$651American Airlines
Find Deal
Tue, May 20 - Tue, Jun 3
11:23 am - 5:40 amKOA-ORD
13h 17m2 stops
6:00 am - 1:34 pmORD-KOA
12h 34m1 stop
$669Alaska Airlines
Find Deal
Tue, May 20 - Tue, Jun 3
11:23 am - 5:40 amKOA-ORD
13h 17m2 stops
6:00 am - 3:25 pmORD-KOA
14h 25m2 stops
$674Alaska Airlines
Find Deal
Tue, May 20 - Tue, Jun 3
1:37 pm - 5:08 amKOA-ORD
10h 31m1 stop
5:38 pm - 12:07 pmORD-KOA
23h 29m1 stop
$720American Airlines
Find Deal
Wed, May 21 - Tue, Jun 3
1:30 pm - 5:04 amKOA-ORD
10h 34m1 stop
9:10 pm - 11:20 amORD-KOA
19h 10m2 stops
$830United Airlines
Find Deal
Mon, Jul 21 - Thu, Jul 24
1:15 pm - 11:46 amKOA-ORD
17h 31m2 stops
6:00 am - 7:16 pmORD-KOA
18h 16m2 stops
$868United Airlines
Find Deal
Mon, Jul 21 - Thu, Jul 24
6:00 am - 12:30 amKOA-MDW
13h 30m2 stops
5:30 am - 12:10 pmMDW-KOA
11h 40m1 stop
$938Southwest
Find Deal
Mon, Jul 21 - Thu, Jul 24
6:00 am - 12:30 amKOA-MDW
13h 30m2 stops
5:50 am - 5:55 pmMDW-KOA
17h 05m2 stops
$944Southwest
Find Deal
Mon, Jul 21 - Thu, Jul 24

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 round-trip flights from Kailua-Kona to Chicago.
Our data shows that the cheapest route for a return flight from Kailua-Kona to Chicago cost $725 and was between Kailua-Kona (KOA) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $725.

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.

Good to know

Low season

August

High season

February

Cheapest flight

$268
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 16% 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 $268 for a one-way ticket and $435 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 $324 or less one-way.

Prefer to fly direct from Kailua-Kona 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

Lufthansa, United Airlines

Lufthansa, United Airlines

See more direct flights

Direct 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 9688 reviews
7.1Food
7.1Entertainment
8.2Boarding
8.5Crew
7.9Comfort
Airline reviews

We had TSA pre check and paid to get it! They told us we would not have to do many of the things such as take your shoes off which I had to do! I’m 78 years old with NO criminal record and. they also patted my ankles down, Why? We boarded the plane in an orderly fashion only to sit there while they perform repairs to the lavatory. Why didn’t they do that before we boarded? I also paid extra to have more room because of my age but that was not what I had hoped for. I know you can’t control who sit in what seat but the guy next to me was bigger than average and took up part of my space.

8.0 ExcellentMichael Deon, Dec 2024HNL - PDX
Read more Alaska Airlines reviews

We had TSA pre check and paid to get it! They told us we would not have to do many of the things such as take your shoes off which I had to do! I’m 78 years old with NO criminal record and. they also patted my ankles down, Why? We boarded the plane in an orderly fashion only to sit there while they perform repairs to the lavatory. Why didn’t they do that before we boarded? I also paid extra to have more room because of my age but that was not what I had hoped for. I know you can’t control who sit in what seat but the guy next to me was bigger than average and took up part of my space.

I was able to upgrade to first class, which was great. Food and drinks were underwhelming compared to other first class flights I have taken.

I purchased a flight to Hawaii, changing planes in San Diego. My flight change location was later changed to Seattle then on to Kona, adding hours to my already long flight. Also, my flight home was run through Portland rather than through San Diego, once again, adding hours to my flight. At 81 years old I don’t want hours robbed from me.

I flew from San Francisco to Honolulu on Hawaiian Airlines. The flight was operated by Alaska Airlines. Everything was fantastic. On the return flight from Honolulu to San Francisco, boarding was chaotic. They called each boarding group 1 through 6 very quickly, and everyone just ran and got in a very long line. There was no enforcement of boarding groups. Carry-on rules were not followed, and by the time I boarded the plane, there was barely any overhead space. I was boarding group 4. The crew was very professional, and the Hawaiian Airlines terminal in Honolulu was beautiful. I wish the rest of Honolulu Airport looked like the Hawaiian Airlines Terminal.

Broke the wheels of my luggage. Should be more gentle with other peoples belongings. Very upset about needing a new suitcase before Christmas.

I was able to upgrade easily on the way home to first class. No problems with luggage. Efficient time management getting us to our destination on time

Rated meals and entertainment poor because we didn’t have any.

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.

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

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.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

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.

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

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