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Find cheap flights from Chicago to The Big Island 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 from Chicago to The Big Island departing on 6/3. 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
Sun 5/26
Sun 6/2

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Best The Big Island Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Kailua-Kona
Kailua-Kona1 stop$422
Hilo
Hilo2 stops$1,469

Good to know

Low season

September

High season

February

Cheapest flight

$211
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Chicago O'Hare Airport to Kailua-Kona

FAQs - booking The Big Island flights

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

    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 Chicago to The Big Island.

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

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

    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 The Big Island with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to The Big Island?

    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 The Big Island from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 airlines serving from Chicago to The Big Island

 
Need help choosing which airline to fly with from Chicago to The Big Island? 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 9115 reviews
8.6crew
7.3entertainment
7.3food
7.9comfort
8.2boarding
Airline reviews

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

10.0 ExcellentAnonymous, Apr 2024SEA - ORD
Read more about Alaska Airlines reviews

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.

It was our baby’s first flight and everything went perfect. The flight attendant gave him his first set of wings and we were smooth flying from there.

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

While the flight and the legroom was good boarding took a long time. The different groups Boarding made no sense as those in the back of the flight boarded last causing delays as people try to find room for their luggage in the upper bins. While there were plenty of seats on the flights We were spaced so that some rows were filled and others were empty. My first flight was very crowded and uncomfortable. On the way back both flights did not have Wi-Fi nor the entertainment package. We were only made aware of this a few hours before the flight. Since the flight was in the morning, I was asleep and was not able to download Books or other media to my phone. This is my first time flying Alaska airlines and I will admit to thinking twice before I do so again.

Our flight was delayed by six hours, our plane never left Portland the night before but the airline didn’t inform anyone till two hours before a six am flight. The plane, our plane never left the west coast! No plane no flight, simply let folks know when you know, not hours and hours later. No one apologized, no one said much of anything, we were just expected to wait quietly and await instructions.

I liked the fast internet and twice serving of snacks and drinks. Paid food options could have included more.

I’m a first time mom and traveled with my 18mo old boy and it was not a great experience with the flight attendants. They were not friendly or helpful at all. It’s hard enough traveling with a toddler and have people be rude and unkind does not help.

Pretty terrible. The aisles on this flight were too narrow so we had to carry our baby, care seat, luggage, travel stroller step by step down the aisle slowing down a lot of passengers in the process. Not only was this a safety hazard but remember that scene from game of thrones where Cersei walks naked through the streets? It felt about as excruciating as that except both me and my husband were carrying 50lbs of weight while everyone from the flight attendants and passengers dolled out comments like “that stroller doesn’t fit in the overhead compartment and you should check it at the gate” when it is a travel stroller that absolutely fits and did fit in the overhead compartment. The flight said it was 30 min delayed but in actuality we did not take off until 1.5 hours past the original time. It was absolutely terrible. Alaska also charged us 200 dollars just in baggage fees even tho we took the time to buy two check on baggages via their app and bought an extra seat for our child and they still refused to overlook our first time flying with them. Everyone in general looked super miserable and traveling with them with a child is pretty much untenable. Lastly I originally thought I had booked an AM flight for my family but it was a PM flight which I knew was not going to end well since we had a 1.5 year old with us on a flight that gets in 9p. I ended up calling Alaska to try to change the first leg for a change fee, and would even have accepted half of a refund to book a completely different flight but of course they refused and absolutely allowed no flexibility to plans so I guess my revenge was our baby cried for 3 out of the four hour flight and hopefully convinced every miserable person on that flight to never fly Alaska again 🤷🏻‍♀️

Window seat and a packed plane. A very uncomfortable flight.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Unfortunately our flight was delayed by 45 minutes due to Kate arriving aircraft. Once we stated everything was great.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Book cheap flights from Chicago to The Big Island

Recent round-trip flight deals

5/12Sun
1 stopAlaska Airlines
20h 26mORD-KOA
5/17Fri
1 stopAlaska Airlines
27h 42mKOA-ORD
$422
5/10Fri
2 stopsAmerican Airlines
15h 28mORD-KOA
5/19Sun
1 stopAmerican Airlines
21h 30mKOA-ORD
$483
5/31Fri
1 stopAlaska Airlines
33h 37mORD-KOA
6/5Wed
1 stopAlaska Airlines
27h 33mKOA-ORD
$503
5/11Sat
2 stopsDelta
16h 26mORD-KOA
5/19Sun
1 stopDelta
10h 54mKOA-ORD
$507
5/12Sun
1 stopAlaska Airlines
20h 26mORD-KOA
5/17Fri
2 stopsAlaska Airlines
28h 22mKOA-ORD
$510
5/9Thu
1 stopAlaska Airlines
32h 09mORD-KOA
5/13Mon
1 stopAlaska Airlines
22h 33mKOA-ORD
$515
5/3Fri
1 stopDelta
16h 32mORD-KOA
5/10Fri
2 stopsDelta
13h 00mKOA-ORD
$521
5/13Mon
1 stopUnited Airlines
13h 24mORD-KOA
5/21Tue
1 stopUnited Airlines
12h 38mKOA-ORD
$562
5/11Sat
2 stopsUnited Airlines
17h 37mORD-KOA
5/18Sat
1 stopUnited Airlines
11h 29mKOA-ORD
$567
5/15Wed
1 stopAmerican Airlines
12h 23mORD-KOA
5/22Wed
1 stopAmerican Airlines
10h 55mKOA-ORD
$581

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Recent one-way flight deals

6/3Mon
1 stopAlaska Airlines
19h 59mORD-KOA
$211
6/11Tue
1 stopAlaska Airlines
18h 50mORD-KOA
$255
6/5Wed
1 stopAlaska Airlines
19h 59mORD-KOA
$292
6/8Sat
1 stopAlaska Airlines
32h 31mORD-KOA
$305
6/7Fri
1 stopDelta
14h 34mORD-KOA
$321
6/20Thu
1 stopUnited Airlines
13h 12mORD-KOA
$390
6/2Sun
1 stopUnited Airlines
26h 54mORD-KOA
$398
8/6Tue
2 stopsDelta
15h 49mMDW-ITO
$450
5/1Wed
2 stopsAmerican Airlines
15h 33mORD-KOA
$474
5/19Sun
2 stopsAmerican Airlines
16h 48mORD-ITO
$609

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Last minute flights from Chicago to The Big Island

Last minute flight, train and bus deals

4/27Sat
multi-stopAlaska Airlines
30h 44mORD-KOA
5/4Sat
multi-stopAlaska Airlines
10h 45mKOA-ORD
$609
4/27Sat
multi-stopAmerican Airlines
11h 08mORD-KOA
5/4Sat
multi-stopAmerican Airlines
9h 58mKOA-ORD
$610
4/27Sat
multi-stopAmerican Airlines
15h 33mORD-KOA
5/4Sat
multi-stopAmerican Airlines
10h 37mKOA-ORD
$613
4/27Sat
multi-stopAmerican Airlines
15h 33mORD-KOA
5/4Sat
multi-stopAmerican Airlines
13h 55mKOA-ORD
$618
5/1Wed
multi-stopAlaska Airlines
32h 09mORD-KOA
5/7Tue
multi-stopAlaska Airlines
10h 45mKOA-ORD
$731
5/1Wed
multi-stopAlaska Airlines
32h 09mORD-KOA
5/8Wed
multi-stopAlaska Airlines
30h 58mKOA-ORD
$735
5/1Wed
multi-stopUnited Airlines
14h 12mORD-KOA
5/7Tue
multi-stopUnited Airlines
26h 02mKOA-ORD
$847
5/1Wed
multi-stopUnited Airlines
14h 12mORD-KOA
5/8Wed
multi-stopUnited Airlines
10h 45mKOA-ORD
$877
5/1Wed
multi-stopDelta
17h 04mMDW-KOA
5/7Tue
multi-stopDelta
15h 27mKOA-MDW
$911
4/27Sat
multi-stopDelta
15h 58mORD-ITO
5/2Thu
multi-stopDelta
16h 31mITO-ORD
$918

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Flights to The Big Island

Return flight deals:

The Big Island - Chicago

Cabin classes:

$311
$328
$277
$32