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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 7/21. 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
Δευ 6/3
Δευ 6/10

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Good to know

Low season

December

High season

May

Cheapest flight

$211
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 14% increase in price.
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 9137 reviews
7.9Comfort
8.6Crew
8.2Boarding
7.3Food
7.3Entertainment
Airline reviews

There was a row with three women who were very loud - talking and laughing. In an open, outdoor setting that's fine. On an airplane, no. The flight attendants told the women they were the fun row. It took the woman sitting in the row ahead of the loud women to tell them they were too loud, but everyone in the general vicinity was irritated. I didn't think it would be possible to be so rowdy for so long. Then when we landed we weren't let off at a gate. We had to be bussed in and the bus contended with airline traffic. After dealing with the loud passengers, this was not what I was expecting. An incredibly disappointing experience with an airline that I have always regarded as one of the better ones.

4.0 OkayElizabeth, May 2024ATL - SEA
Read more about Alaska Airlines reviews

There was a row with three women who were very loud - talking and laughing. In an open, outdoor setting that's fine. On an airplane, no. The flight attendants told the women they were the fun row. It took the woman sitting in the row ahead of the loud women to tell them they were too loud, but everyone in the general vicinity was irritated. I didn't think it would be possible to be so rowdy for so long. Then when we landed we weren't let off at a gate. We had to be bussed in and the bus contended with airline traffic. After dealing with the loud passengers, this was not what I was expecting. An incredibly disappointing experience with an airline that I have always regarded as one of the better ones.

I bought the cheapest ticket. No meal, no checked luggage so I didn't expect much and was surprised by how good the flight and service was. Alaska is now my favorite airline.

Comfortable seat, plenty of leg room which is so rare, overhead bin comfortably accommodated my carry-on bag. Deli box was tasty, service was good, bathrooms were clean. Uneventful flight, which I appreciate. Departed on time and landed early.

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

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

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.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Book cheap flights from The Big Island to Chicago

Recent round-trip flight deals

10/24Πεμ
1 stopDelta
10h 33mKOA-ORD
11/1Παρ
1 stopDelta
14h 56mORD-KOA
$542
10/24Πεμ
2 stopsDelta
15h 12mKOA-ORD
11/1Παρ
1 stopDelta
14h 56mORD-KOA
$547
10/24Πεμ
2 stopsDelta
15h 12mKOA-ORD
11/1Παρ
2 stopsDelta
16h 08mORD-KOA
$577

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Recent one-way flight deals

7/21Κυρ
1 stopDelta
14h 42mKOA-ORD
$211
7/17Τετ
1 stopDelta
14h 42mKOA-ORD
$251
7/16Τρι
2 stopsDelta
15h 45mKOA-ORD
$256
7/22Δευ
1 stopUnited Airlines
10h 45mKOA-ORD
$261
7/23Τρι
2 stopsAlaska Airlines
13h 16mKOA-ORD
$296
7/22Δευ
2 stopsAlaska Airlines
34h 16mKOA-ORD
$300
6/16Κυρ
1 stopAmerican Airlines
11h 06mKOA-ORD
$305
6/17Δευ
1 stopUnited Airlines
11h 00mKOA-ORD
$316
7/17Τετ
2 stopsAmerican Airlines
13h 47mKOA-ORD
$380
7/20Σαβ
2 stops
16h 40mKOA-ORD
$509

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Last minute flights from The Big Island to Chicago

Last minute flight, train and bus deals

5/7Τρι
multi-stopDelta
10h 54mKOA-ORD
5/14Τρι
multi-stopDelta
17h 28mORD-KOA
$567
5/7Τρι
multi-stopDelta
15h 37mKOA-ORD
5/14Τρι
multi-stopDelta
17h 28mORD-KOA
$572
5/8Τετ
multi-stopAlaska Airlines
16h 58mKOA-ORD
5/14Τρι
multi-stopAlaska Airlines
11h 40mORD-KOA
$580
5/7Τρι
multi-stopDelta
10h 54mKOA-ORD
5/10Παρ
multi-stopDelta
16h 27mORD-KOA
$586
5/7Τρι
multi-stopDelta
10h 54mKOA-ORD
5/10Παρ
multi-stopDelta
15h 50mORD-KOA
$591
5/7Τρι
multi-stopAlaska Airlines
12h 45mKOA-ORD
5/10Παρ
multi-stopAlaska Airlines
27h 54mORD-KOA
$670
5/6Δευ
multi-stopAmerican Airlines
9h 51mKOA-ORD
5/13Δευ
multi-stopAmerican Airlines
12h 23mORD-KOA
$704
5/6Δευ
multi-stopAmerican Airlines
11h 33mKOA-ORD
5/13Δευ
multi-stopAmerican Airlines
15h 33mORD-KOA
$709
5/7Τρι
multi-stopUnited Airlines
10h 45mKOA-ORD
5/13Δευ
multi-stopUnited Airlines
15h 20mORD-KOA
$725
5/7Τρι
multi-stopUnited Airlines
13h 12mKOA-ORD
5/10Παρ
multi-stopUnited Airlines
14h 11mORD-KOA
$961

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Flights to Chicago

Return flight deals:

Chicago - The Big Island

Cabin classes:

$274
$293
$219
$38