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Find cheap flights from The Big Island to Chicago from $211

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 5/28. 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
Fri 6/7
Fri 6/14

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Good to know

Low season

August

High season

February

Cheapest flight

$211
Best time to beat the crowds with an average 5% 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

FAQs for booking flights from The Big Island to Chicago

  • How does KAYAK find such low prices on flights from The Big Island 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 The Big Island to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from The Big Island to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from The Big Island 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 The Big Island 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 The Big Island with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from The Big Island 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 The Big Island up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from The Big Island to Chicago?

Find which airlines fly direct from The Big Island to Chicago, which days they fly and book direct flights.

Nonstop departures

The Big Island to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to The Big Island

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

Top 3 airlines serving from The Big Island to Chicago

 
Need help choosing which airline to fly with from The Big Island 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 9141 reviews
7.9Comfort
8.2Boarding
8.6Crew
7.3Food
7.3Entertainment
Airline reviews

No tv, movies for a 6 hour flight! Worst airline I have ever travelled!

6.0 GoodAnonymous, May 2024JFK - SFO
Read more about Alaska Airlines reviews

No tv, movies for a 6 hour flight! Worst airline I have ever travelled!

boarding was easy and the 737 Max was comfortable and roomy but that was the only good.. there was a child screaming at the top of his lungs for the entire loading, taxiing and part of the flight and no one in the crew said anything or offered any assistance.

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.

Quick easy boarding. Airport was unprepared for early landing and we were waiting in the plane for 20 minutes before getting a gate.

Due to delayed flight, we missed our connecting flight as well as had to wait for 11 hours for next availaible flight. Not good experience

All employees were very nice and I was very comfortable

Seat did not recline yet fare was the same as one that did !!!

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

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.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Book cheap flights from The Big Island to Chicago

Recent round-trip flight deals

8/26Mon
2 stopsDelta
15h 14mKOA-ORD
9/24Tue
1 stopDelta
14h 56mORD-KOA
$466
8/26Mon
2 stopsDelta
15h 14mKOA-ORD
9/24Tue
2 stopsDelta
14h 39mORD-KOA
$471
8/26Mon
1 stopAmerican Airlines
11h 33mKOA-ORD
9/24Tue
1 stopAmerican Airlines
22h 56mORD-KOA
$479
10/24Thu
1 stopDelta
10h 33mKOA-ORD
11/1Fri
1 stopDelta
14h 56mORD-KOA
$542
10/24Thu
2 stopsDelta
15h 12mKOA-ORD
11/1Fri
1 stopDelta
14h 56mORD-KOA
$547
6/16Sun
1 stopDelta
10h 34mKOA-ORD
8/8Thu
1 stopDelta
14h 44mORD-KOA
$556
6/7Fri
1 stopUnited Airlines
11h 57mKOA-ORD
6/14Fri
1 stopUnited Airlines
13h 12mORD-KOA
$624
6/7Fri
2 stopsAmerican Airlines
14h 49mKOA-ORD
6/14Fri
1 stopAmerican Airlines
11h 51mORD-KOA
$691
6/20Thu
1 stopAlaska Airlines
11h 46mKOA-ORD
6/30Sun
1 stopAlaska Airlines
28h 38mORD-KOA
$723
6/16Sun
2 stopsUnited Airlines
16h 46mKOA-ORD
8/8Thu
2 stopsUnited Airlines
18h 54mORD-KOA
$728

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Recent one-way flight deals

5/28Tue
1 stopAmerican Airlines
10h 55mKOA-ORD
$211
5/28Tue
2 stopsAmerican Airlines
13h 30mKOA-ORD
$216
5/16Thu
1 stopUnited Airlines
11h 29mKOA-ORD
$220
7/3Wed
1 stopUnited Airlines
10h 45mKOA-ORD
$243
8/23Fri
2 stopsDelta
15h 14mKOA-ORD
$248
8/5Mon
1 stopDelta
10h 43mKOA-ORD
$251
9/16Mon
1 stopDelta
10h 33mKOA-ORD
$252
9/16Mon
2 stopsDelta
15h 58mKOA-ORD
$257
7/3Wed
2 stopsAlaska Airlines
13h 16mKOA-ORD
$281
8/6Tue
2 stopsAlaska Airlines
26h 23mKOA-ORD
$332

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Last minute flights from The Big Island to Chicago

Last minute flight, train and bus deals

5/12Sun
multi-stopAlaska Airlines
22h 33mKOA-ORD
5/14Tue
multi-stopAlaska Airlines
17h 55mORD-KOA
$520
5/12Sun
multi-stopAlaska Airlines
22h 33mKOA-ORD
5/14Tue
multi-stopAlaska Airlines
19h 55mORD-KOA
$594
5/12Sun
multi-stopDelta
21h 25mKOA-ORD
5/14Tue
multi-stopDelta
15h 50mORD-KOA
$620
5/12Sun
multi-stopDelta
17h 01mKOA-ORD
5/14Tue
multi-stopDelta
15h 50mORD-KOA
$641
5/12Sun
multi-stopDelta
17h 54mKOA-ORD
5/14Tue
multi-stopDelta
15h 50mORD-KOA
$642
5/12Sun
multi-stopDelta
17h 54mKOA-ORD
5/14Tue
multi-stopDelta
17h 28mORD-KOA
$664

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Flights to Chicago

Return flight deals:

Chicago - The Big Island

Cabin classes:

$333
$301
$219
$38