ORD

$190 Find Cheap Flights from The Big Island to Chicago O'Hare Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to O'Hare Intl departing on 12/14. 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

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Everything you should know

Cheapest round-trip
$389
Overall average: $705
Alaska Airlines
Tue 3/3Wed 3/4
KOA - ORD • 2 stops
Cheapest one-way
$190
Typical prices: $376-$500
Multiple Airlines
Sun 12/14
KOA - ORD • 2 stops
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Flight Deals
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Flight Deals

Cheap Flights from The Big Island to O'Hare Intl

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from The Big Island to O'Hare Intl 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 The Big Island to O'Hare Intl

Tue, Mar 3 - Wed, Mar 4
Alaska Airlines Logo
6:00 am - 11:10 pmKOA-ORD
13h 10m2 stops
Alaska Airlines Logo
2:59 pm - 2:46 pmORD-KOA
27h 47m1 stop
$389Alaska Airlines
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Tue, Mar 3 - Wed, Mar 4
Alaska Airlines Logo
6:00 am - 11:10 pmKOA-ORD
13h 10m2 stops
Alaska Airlines Logo
2:59 pm - 2:46 pmORD-KOA
27h 47m1 stop
$399Alaska Airlines
Find Deal
Tue, Mar 3 - Wed, Mar 4
Alaska Airlines Logo
12:00 pm - 1:59 pmKOA-ORD
21h 59m1 stop
Alaska Airlines Logo
6:50 pm - 10:35 pmORD-KOA
31h 45m1 stop
$433Alaska Airlines
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Tue, Nov 25 - Sun, Nov 30
American Airlines Logo
6:25 pm - 10:36 amKOA-ORD
12h 11m1 stop
American Airlines Logo
6:00 am - 3:01 pmORD-KOA
13h 01m1 stop
$572American Airlines
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Tue, Nov 25 - Sun, Nov 30
Southwest Logo
9:15 pm - 2:45 pmKOA-ORD
13h 30m1 stop
Southwest Logo
7:15 am - 9:20 pmORD-KOA
18h 05m2 stops
$798Southwest
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Tue, Nov 25 - Sun, Nov 30
Southwest Logo
6:00 am - 10:35 pmKOA-ORD
12h 35m2 stops
Southwest Logo
7:15 am - 6:10 pmORD-KOA
14h 55m2 stops
$814Southwest
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Tue, Dec 23 - Mon, Dec 29
Delta Logo
1:50 pm - 9:36 amKOA-ORD
15h 46m2 stops
Delta Logo
6:00 am - 8:27 pmORD-KOA
18h 27m2 stops
$894Delta
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Wed, Nov 26 - Sun, Nov 30
United Airlines Logo
4:33 pm - 11:23 amITO-ORD
14h 50m2 stops
United Airlines Logo
9:35 am - 8:28 pmORD-ITO
14h 53m1 stop
$951United Airlines
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Sun, Feb 1 - Fri, Feb 6
United Airlines Logo
3:02 pm - 6:16 amITO-ORD
11h 14m1 stop
United Airlines Logo
9:30 am - 8:29 pmORD-ITO
14h 59m1 stop
$1,840United Airlines
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Sun, Feb 1 - Fri, Feb 6
American Airlines Logo
3:02 pm - 7:00 amITO-ORD
11h 58m1 stop
American Airlines Logo
9:02 am - 10:34 pmORD-ITO
17h 32m2 stops
$2,709American Airlines
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Good to know

Low seasonJanuary
Cheapest flight$190
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Kailua-Kona to Chicago O'Hare Airport

FAQs for booking The Big Island to Chicago O'Hare Airport flights

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

    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 O'Hare Airport.

  • 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 O'Hare Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport 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 O'Hare Airport?

    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 O'Hare Airport 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 O'Hare Airport?

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

Reviews of the top 4 airlines serving from The Big Island to O'Hare Intl

 
Need help choosing which airline to fly with from The Big Island to O'Hare Intl? 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 11214 reviews
7.8Comfort
7.0Entertainment
8.5Crew
8.1Boarding
7.1Food
Airline reviews

Check in online didn't accept my confirmation number so i could only check in with assistance at the airport and ended up with s creepy middle seat.

4.0 OkayMarco, Oct 2025SAN - ORD
Read more Alaska Airlines reviews

Check in online didn't accept my confirmation number so i could only check in with assistance at the airport and ended up with s creepy middle seat.

It was the most expensive Alaska Airlines ticket I’ve ever purchased. I had a middle seat with no legroom or space compared to any other middle seat I’ve hadThere was a silver box under the seat that took up 70% of my legroom on the most narrow 737 max the crew flat out would not help they would not help with bags they would not help with garbage there was no coffee,It was definitely not one of my better experiences on Alaska.

Once again, Hawaiian Airlines upon checking in for our return flight, told us that we hadn’t paid for our extra comfort seats. This had happened on our incoming flight as well. Hawaiian Airlines had changed our flight and put us in standard seats. I sent them confirmation emails and receipts showing that I had paid for extra comfort seats and they ignored me and refused to accept my proof of payment. I ended up having to pay for our extra comfort seats again. On our return flight, once again, we were told we hadn’t paid for our extra comfort seats, which we had. I argued until a supervisor was summoned and researched further in their system and found that we had paid for them. If I hadn’t insisted, we would’ve been forced to buy our seats again or be assigned a standard seat. This kind of Customer Service is totally unacceptable. I would never use Hawaiian Airlines again if I have a choice.

The stewards were too loud and chatty with each other

If the flight from Seattle to Eugene hadn’t been delayed for mechanical reasons we never would have made it. 45 minutes is not enough time to deplane and get clear across a big airport like SeaTac.

This was a smooth ride all the way with plenty of space in main cabin for my 6 foot frame over 5.5 hours. The stewards were pleasant and attentive. We bought the tapas box which proved to adequate for us on this flight. It was pretty hard to find restaurant food to go that is vegan for us in Kona Airport so buying this helped lots.

set room is an issue and I am not obese.

Look at my previous review I just wrote on this survey. It was awful!

My experience from Lihue Airport was the “Flight Experience from Hell!” First, I was pulled aside by the Lihue TSA and searched thoroughly! Not once, but twice I was molested by 5 different TSA agents using some sort of smear cloth testing to see if I had been exposed to something dangerous! I can’t tell you what because they never gave me an explanation by the end of a near delaying incident of boarding my plane. More importantly, I was generously provided an airport wheel chair and personal porter because of my health condition. TSA even took your wheelchair apart! What’s up with that? I’m near 75, caucasian, never been arrested for anything, don’t do drugs or alcohol, and patiently and politely abided to their instructions for a full damn 20 minutes! Awful and humiliating experience especially when two different agents literally groped my testicles and crack of my butt! Then they lost the cap to my inhaler. When I got to my destination, a whole bottle of prescribed pills were emptied because of them not tightening the cap back on! Total BS and unprofessional by the lot of them! The short flight to my connecting flight to the mainland on Maui fortunately was uneventful. However the Hawaiian aircraft to San Jose was one of the worst flights I’ve ever experienced without crashing. I believe it was a 330 Neo. May I ask, why did you put three more rows of seats in the damn plane since I last flew on a Hawaiian aircraft? I had absolutely NO legroom compared to the last time I flew with you. And I’ve done a few Hawaii/mainland trips, even a RT to New Zealand before. Then, the icing on the cake was a couple with a one year old baby that literally cried and screamed for all but 15 minutes of the 5 hour flight to San Jose! Further, I couldn’t move my seat back even a millimeter because a car seat was placed from their window seat to the back of my seat! My Hawaiian flight was a freaking nightmare and fortunately will be flying back to Lihue direct with Alaska!

I only give it a bad rating because I missed my flight

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

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