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KOA - CHI

$211 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 10/24. 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
Thu 6/27
Thu 7/4

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 42,816,550 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
12:29 pm - 5:15 amKOA-ORD
11h 46m1 stop
9:22 pm - 9:00 pmORD-KOA
28h 38m1 stop
$422Alaska Airlines
Find Deal
Wed, Jul 31 - Tue, Aug 6
8:41 pm - 2:44 pmKOA-ORD
13h 03m2 stops
7:26 am - 5:22 pmORD-KOA
14h 56m1 stop
$467Delta
Find Deal
Mon, Aug 26 - Tue, Sep 24
8:41 pm - 2:44 pmKOA-ORD
13h 03m2 stops
7:10 am - 6:34 pmORD-KOA
16h 24m2 stops
$472Delta
Find Deal
Mon, Aug 26 - Tue, Sep 24
1:40 pm - 5:30 amKOA-ORD
10h 50m1 stop
1:18 pm - 12:30 pmORD-KOA
28h 12m1 stop
$500Alaska Airlines
Find Deal
Mon, Aug 26 - Tue, Sep 24
7:35 pm - 11:20 amKOA-ORD
10h 45m1 stop
12:55 pm - 9:22 pmORD-KOA
13h 27m1 stop
$512United Airlines
Find Deal
Sun, Jul 28 - Sun, Aug 4
8:41 pm - 6:38 pmKOA-MDW
16h 57m2 stops
9:35 am - 6:34 pmMDW-KOA
13h 59m2 stops
$525Delta
Find Deal
Mon, Aug 26 - Tue, Sep 24
1:35 pm - 12:40 pmKOA-ORD
18h 05m1 stop
6:25 pm - 12:05 pmORD-KOA
22h 40m1 stop
$537American Airlines
Find Deal
Fri, Oct 18 - Sat, Oct 19
1:30 pm - 5:30 amKOA-ORD
11h 00m1 stop
5:45 pm - 9:07 pmORD-KOA
32h 22m2 stops
$545Alaska Airlines
Find Deal
Fri, Oct 18 - Sat, Oct 19
9:30 pm - 1:05 pmKOA-ORD
10h 35m1 stop
7:00 am - 5:07 pmORD-KOA
15h 07m1 stop
$557Delta
Find Deal
Sun, Jul 28 - Sun, Aug 4
10:18 am - 4:56 amKOA-ORD
13h 38m2 stops
10:45 am - 9:22 pmORD-KOA
15h 37m2 stops
$730United Airlines
Find Deal
Wed, Jul 31 - Tue, Aug 6
3:09 pm - 4:15 pmKOA-ORD
20h 06m1 stop
$211Alaska Airlines
Find Deal
Thu, Oct 24
8:45 pm - 6:05 pmKOA-MDW
16h 20m2 stops
$216Delta
Find Deal
Wed, Oct 30
9:45 pm - 5:57 pmKOA-ORD
15h 12m2 stops
$216Delta
Find Deal
Thu, Oct 24
9:45 pm - 1:18 pmKOA-ORD
10h 33m1 stop
$233Delta
Find Deal
Thu, Oct 24
8:41 pm - 4:50 pmKOA-ORD
15h 09m2 stops
$238Delta
Find Deal
Fri, Aug 23
3:08 pm - 4:48 pmKOA-ORD
20h 40m2 stops
$255Alaska Airlines
Find Deal
Tue, Oct 29
10:25 pm - 3:14 pmKOA-ORD
11h 49m1 stop
$260American Airlines
Find Deal
Mon, Sep 16
1:52 pm - 8:52 amKOA-ORD
14h 00m2 stops
$265American Airlines
Find Deal
Mon, Sep 16
11:15 pm - 6:00 amKOA-ORD
25h 45m1 stop
$370United Airlines
Find Deal
Sun, Jun 23
11:15 pm - 9:01 pmKOA-ORD
16h 46m2 stops
$376United Airlines
Find Deal
Sun, Jun 23

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 $295 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 $1,274.

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, Monday 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 Wednesday, with Saturday being the most expensive.

Which airlines provide the cheapest flights from Kailua-Kona to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the past 3 days, the cheapest one-way tickets to Chicago from Kailua-Kona were found on Alaska Airlines ($211) and Delta ($216), and the lowest round-trip tickets were found on Alaska Airlines ($422) and Delta ($467).

Which cabin class options are there for flights between Kailua-Kona and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 3 cabin class options for the route. These are Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Good to know

Low season

August

High season

February

Cheapest flight

$211
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 19% 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 $211 for a one-way ticket and $422 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?

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

  • 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 $532 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 $644 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

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 9192 reviews
8.6Crew
7.9Comfort
8.2Boarding
7.3Entertainment
7.3Food
Airline reviews

Flights were on time. Check in was fine. Crew members were pleasant.

10.0 ExcellentAnonymous, May 2024TUS - SEA
Read more about Alaska Airlines reviews

Flights were on time. Check in was fine. Crew members were pleasant.

The boarding gate is literally just an aisle to the concourse. There is no seating and it's shared with several other airlines. It's crowded, hot, and standing-room only. It's difficult to hear gate announcements over the PA system with too many other carriers crammed into a small space. I've enjoyed flying AA in the past on the west coast, but the BNA single gate experience is horrendous! Never again from BNA to SEA with AA.

I would have liked it to have been easier to order food for the flight. My son was not happy with the snack pack I bought him and it was a very long flight for a little boy to go without food.

1309 on May had some very bumpy segments that seem to take too long to get to smoother air. My initial flight out of GRR was delayed and missed connections. Sure glad I made a different one in ORD so I could be in Anchorage.

It was warm on the plane. Perhaps the people who were coughing quite often should be encouraged to wear a mask?! It was a long 4 hours.

Flight was late but crew was very efficient and friendly.

Like South West(2 check in baggage free) if Alaskan Airlines could give at least one check in baggage free then it would be great.

Was not happy that we had to wait an additional 50 minutes for passengers that were still in TSA. This delay made us miss our connecting flight in Seattle to get home to tuck in our two little toddlers. We ran off the plane and ran across the entire airport trying to make this flight only to get to the gate to see that they have ended boarding. So they were willing to wait for passengers in Hawaii but not Seattle?? Especially when this wasn't even our fault. I expect to receive miles for missing our flight and spending an additional 4 hours in Seattle.

I usually choose Alaska Airlines over any other airline. They try the hardest to make flying a great experience.

Staff being friendly would have help since the flight was delayed, again. Folks answered questions but no one seemed happy to be working today and if showed.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

Our flight was great we left Kona earlier and got into LAX almost an 1hour earlier as well. LAX AA is in repair so to get out and found our bus to get pick up was a bit confusing.

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

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.
10/24Thu
1 stopAlaska Airlines
20h 06mKOA-ORD
$211
10/30Wed
2 stopsDelta
16h 20mKOA-MDW
$216
10/24Thu
2 stopsDelta
15h 12mKOA-ORD
$216
10/24Thu
1 stopDelta
10h 33mKOA-ORD
$233
8/23Fri
2 stopsDelta
15h 09mKOA-ORD
$238
10/29Tue
2 stopsAlaska Airlines
20h 40mKOA-ORD
$255
9/16Mon
1 stopAmerican Airlines
11h 49mKOA-ORD
$260
9/16Mon
2 stopsAmerican Airlines
14h 00mKOA-ORD
$265
6/23Sun
1 stopUnited Airlines
25h 45mKOA-ORD
$370
6/23Sun
2 stopsUnited Airlines
16h 46mKOA-ORD
$376

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Kailua-Kona - Chicago Flights

Departure:

Kailua-Kona (KOA)United States

Return flight deals:

Chicago - Kailua-Kona

Cabin classes:

$2,105
$1,274