$171 Find Cheap Flights from Chicago O'Hare Airport to The Big Island

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to The Big Island 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.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to The Big Island

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to The Big Island.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to The Big Island.
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Flight Deals

Cheap Flights from O'Hare Intl to The Big Island

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Kailua-Kona
Kailua-Kona1 stop$382
Hilo
Hilo2 stops$445
Waimea (Big Island)
Waimea (Big Island)2 stops$1,026
Kailua-Kona
Kailua-Kona1 stop$382
Hilo
Hilo2 stops$445
Waimea (Big Island)
Waimea (Big Island)2 stops$1,026

Book Cheap O'Hare Intl to The Big Island Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to The Big Island 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from O'Hare Intl to The Big Island

Wed, Apr 29 - Mon, May 4
Alaska Airlines Logo
3:52 pm - 2:56 pm
ORD
-
KOA
28h 04m
1 stop
Alaska Airlines Logo
1:16 pm - 7:03 pm
KOA
-
ORD
24h 47m
1 stop
$382Alaska Airlines
Wed, Apr 29 - Wed, May 6
Alaska Airlines Logo
3:52 pm - 2:56 pm
ORD
-
KOA
28h 04m
1 stop
Alaska Airlines Logo
1:16 pm - 7:03 pm
KOA
-
ORD
24h 47m
1 stop
$392Alaska Airlines
Tue, Apr 28 - Mon, May 4
Multiple Airlines Logo
8:50 am - 10:16 pm
ORD
-
KOA
18h 26m
2 stops
Multiple Airlines Logo
1:16 pm - 7:03 pm
KOA
-
ORD
24h 47m
1 stop
$398Multiple Airlines
Mon, Apr 27 - Wed, May 6
Alaska Airlines Logo
3:52 pm - 2:56 pm
ORD
-
KOA
28h 04m
1 stop
Alaska Airlines Logo
1:16 pm - 7:03 pm
KOA
-
ORD
24h 47m
1 stop
$402Alaska Airlines
Tue, Feb 24 - Tue, Mar 3
Alaska Airlines Logo
3:07 pm - 3:53 pm
ORD
-
KOA
28h 46m
1 stop
Alaska Airlines Logo
1:10 pm - 2:58 pm
KOA
-
ORD
21h 48m
1 stop
$403Alaska Airlines
Tue, Apr 28 - Thu, May 7
Multiple Airlines Logo
8:50 am - 10:16 pm
ORD
-
KOA
18h 26m
2 stops
Multiple Airlines Logo
1:16 pm - 7:03 pm
KOA
-
ORD
24h 47m
1 stop
$408Multiple Airlines
Sun, May 3 - Thu, May 7
Alaska Airlines Logo
7:59 pm - 2:56 pm
ORD
-
KOA
23h 57m
1 stop
Alaska Airlines Logo
1:16 pm - 7:03 pm
KOA
-
ORD
24h 47m
1 stop
$412Alaska Airlines
Mon, Feb 23 - Tue, Mar 3
Alaska Airlines Logo
3:07 pm - 3:53 pm
ORD
-
KOA
28h 46m
1 stop
Alaska Airlines Logo
1:10 pm - 2:58 pm
KOA
-
ORD
21h 48m
1 stop
$413Alaska Airlines
Tue, Feb 24 - Tue, Mar 3
Multiple Airlines Logo
8:20 am - 7:17 am
ORD
-
KOA
26h 57m
2 stops
Multiple Airlines Logo
7:50 pm - 11:59 pm
KOA
-
ORD
24h 09m
2 stops
$415Multiple Airlines
Wed, Apr 1 - Wed, Apr 15
Southwest Logo
6:15 am - 6:10 pm
ORD
-
ITO
16h 55m
2 stops
Southwest Logo
6:55 pm - 6:50 pm
ITO
-
ORD
18h 55m
2 stops
$675Southwest
Booking Insights

KAYAK's insights & trends for O'Hare Intl to The Big Island flights

Get data-powered insights and trends into flights from O'Hare Intl to The Big Island to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago O'Hare Intl Airport to The Big Island flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to The Big Island from Chicago O'Hare Intl Airport found in the last 72 hours was to Kailua-Kona, at $1,194 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Kailua-Kona (KOA), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $1,194.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to The Big Island?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $425, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to The Big Island?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to The Big Island, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to The Big Island is January, when tickets cost $592 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $1,051 and $813 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to The Big Island?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to The Big Island, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to The Big Island, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$171
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 25% increase in price.
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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport to The Big Island?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport to 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 Chicago O'Hare Airport 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 from Chicago O'Hare Airport to The Big Island with an airline and back with another airline.

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

  • What is the cheapest time of day to fly to The Big Island?

    The cheapest time of day to fly to The Big Island is generally in the morning, when round-trip flights cost $1,392 on average. The most expensive time of day to fly to The Big Island is generally in the morning, which is peak travel time and where the average cost of a ticket is $1,392.

Reviews of the top 5 airlines serving from O'Hare Intl to The Big Island

 
See real verified KAYAK customer reviews for airlines flying from Chicago to The Big Island. 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 O'Hare Intl 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 11807 reviews
8.5Crew
8.1Boarding
7.0Entertainment
7.8Comfort
7.1Food
Airline reviews

The bathroom trash container under the sink fell out and was like that long before my flight. The plane smelled of canned fish and floor was Deteriorating

4.0 OkayTimothy, Jan 2026
LAX - OGG
Read more Alaska Airlines reviews

The bathroom trash container under the sink fell out and was like that long before my flight. The plane smelled of canned fish and floor was Deteriorating

No WiFi. Terrible food. Very long walk to the gate and from the gate after landing. Gate changed without notice.

I really hate the seat assignment at the gate. I understand it is so families can sit together but it caused me and others a lot of unnecessary stress and confusion, enough for me to not fly Alaska again. The app is so awful that it did not even update my seat assignment on the boarding pass but sent me a notification of my seat... it showed in Apple Wallet but not in the Alaska app itself. That only made the stress worse. I think most people like myself prefer to know where they are seated at check in 24 hours before so they don't have to anxiously hang out at the gate the entire time. This is not a good use of your agents time either to be dealing with all of us asking where we are sitting. You should automatically assign the multiple seat purchases to be together before they check in and fill us solo travelers in those gaps as we check in.

Great. Went right to the desk and the people were helpful and kind. I was able to get my boarding pass in under 5minutes. They made sure I received the text.

I behave had better flights this one was old and poor

See previous. It was the flight from Honolulu to Kapalua that was cancelled.

Short trip from Honolulu to Kauai. Not a major issue. Only concern was the drop off of the luggage for departure. Only one person handling all of the passengers. She was busting her butt.

The flight was delayed so we didn’t get into San Diego until almost 1 AM. Otherwise, it was lovely.

Good. Flight was good. Crew was good. Wish they offered coffee refills. Wish I didn’t have to pay for headphones. Otherwise good for a commercial flight.

Should have been forthcoming for reason for delay. Should have been able to check in for seat I'd like.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

The crew at Hawaiian Airlines was fantastic. Kind and hard working. The pilots were great with giving us all the updates to make sure we were informed.

Very good. Nice plane and we sat in economy plus - bigger seats, more room. They served a meal and snacks, and the meal was an apple stuffed pancake that was very good! The snack for us was a hummus sandwich - also very good. The flight attendants were helpful and nice. They have plenty of movies and shows to watch. My only negative -- they changed our flights around and did not adjust the layovers, so we ended up with a very long and unnecessary layover in Honolulu.

Flight scheduled to take off at 5.55pm but it did not take off until 7pm due to some food delivery delay.

The crew was quite good, they came by often with drinks or to collect trash. But what wasn't nice was the flight was over weigh and several people had to be rebooked. I was questioned whether I should have a seat when I was getting to it. The in-flight entertainment kept buffering and interrupting. And the route took the airplane through high winds which caused us a longer flight

Wasn’t on the flight due to Alaska cancellation…also after all the rerouting, I was going to be on a later flight that left SFO at 7:47pm, which meant an almost 6 hour layover. That same Hawaiian flight was delayed for another 2hours.

I always love flying Hawaii and I have nothing to add

Everything was great and smooth. Given the short flight there was no entertainment but the rating does not give this option. My first flight with Hawaiian was a success all around.

comfortable but the food is horrible. I have flown Hawaiian several times now and no matter what they say the food is its the same squashed bread with melted goop inside. Tastes fake and isnt what they represent, its quite nasty. What happend to real food? And there is NO entertainment!! so not sure why they are asking for a review on that.

I was very, very cold and a stranger loaned me her sweater next to me. I didn’t wanna buy a blanket just for a four hour trip when I did not need the pillow or the earphones. I don’t mind purchasing a blanket, but I only needed that not all of it accessories. Cold air pretty much blew the entire trip. Two people in front of me both bought the blanket packages. Maybe that’s the idea. The crew was exceptionally nice and passed through multiple times.. the restrooms were very clean and usually accessible.

3 hour wait on customer service after flight was cancelled. Was bumped to a flight where I wouldnt have gotten to my destination for another 2 days. Had to fully refund flight and book a new one the following morning. Paid twice the amount for the flight than I had originally booked. Very disappointed I was not offered any sort of discount or points for all of the frustration, in fact the airline profited twice as much off of me by cancelling my flight and and changing my entire trip.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

Everything you need to know for your flight to The Big Island

Information on your arrival and departure airports