$205 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 9/6. 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

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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to The Big Island, as well as popular online travel agencies
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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$405
Hilo
Hilo2 stops$419
Kailua-Kona
Kailua-Kona1 stop$405
Hilo
Hilo2 stops$419

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

Tue, Nov 11 - Mon, Nov 17
Alaska Airlines Logo
9:20 am - 2:43 pmORD-KOA
33h 23m1 stop
Alaska Airlines Logo
12:09 pm - 1:54 pmKOA-ORD
21h 45m1 stop
$405Alaska Airlines
Find Deal
Wed, Oct 8 - Wed, Oct 22
American Airlines Logo
6:03 am - 1:58 pmORD-KOA
12h 55m1 stop
American Airlines Logo
9:45 pm - 2:15 pmKOA-ORD
11h 30m1 stop
$406American Airlines
Find Deal
Wed, Oct 8 - Wed, Oct 22
American Airlines Logo
6:03 am - 1:58 pmORD-KOA
12h 55m1 stop
American Airlines Logo
9:45 pm - 2:15 pmKOA-ORD
11h 30m1 stop
$407American Airlines
Find Deal
Thu, Jan 15 - Sun, Jan 25
Alaska Airlines Logo
2:59 pm - 2:46 pmORD-KOA
27h 47m1 stop
Alaska Airlines Logo
12:00 pm - 1:59 pmKOA-ORD
21h 59m1 stop
$408Alaska Airlines
Find Deal
Sun, Jan 11 - Mon, Jan 19
Delta Logo
7:15 am - 3:50 pmORD-KOA
12h 35m1 stop
Delta Logo
8:45 pm - 1:25 pmKOA-ORD
12h 40m1 stop
$423Delta
Find Deal
Thu, Oct 30 - Fri, Nov 7
Delta Logo
7:37 am - 5:30 pmORD-KOA
14h 53m1 stop
Delta Logo
9:30 pm - 5:18 pmKOA-ORD
15h 48m1 stop
$435Delta
Find Deal
Tue, Sep 2 - Tue, Sep 9
Southwest Logo
6:15 am - 6:10 pmORD-ITO
16h 55m2 stops
Southwest Logo
3:25 pm - 2:25 pmITO-ORD
18h 00m2 stops
$532Southwest
Find Deal
Tue, Aug 12 - Fri, Sep 12
Southwest Logo
6:15 am - 6:10 pmORD-ITO
16h 55m2 stops
Southwest Logo
6:55 pm - 5:55 pmITO-ORD
18h 00m2 stops
$697Southwest
Find Deal
Mon, Nov 3 - Mon, Nov 10
United Airlines Logo
9:35 am - 7:01 pmORD-ITO
13h 26m1 stop
United Airlines Logo
7:43 pm - 6:08 amITO-ORD
30h 25m1 stop
$733United Airlines
Find Deal
Mon, Nov 3 - Mon, Nov 10
United Airlines Logo
9:35 am - 7:01 pmORD-ITO
13h 26m1 stop
United Airlines Logo
7:43 pm - 6:08 amITO-ORD
30h 25m1 stop
$735United Airlines
Find Deal
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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago O'Hare Intl Airport to The Big Island.

The cheapest ticket to The Big Island from Chicago O'Hare Intl Airport found in the last 72 hours was to Kailua-Kona, at $1,243 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 $1,243.

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 $1,038, 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 November, when tickets cost $593 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $831 and $826 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to The Big Island?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to The Big Island clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to The Big Island on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Chicago O'Hare Airport to The Big Island. For your return ticket, we recommend flying on a Monday and avoiding Saturdays for the best deals.

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 2 weeks before departure, which saves you about 14% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.


Good to know

Low seasonNovember
Cheapest flight$205
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 12% 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 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 at night, when round-trip flights cost $639 on average. Morning departures are around 59% more expensive than evening flights, 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 $1,190.

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 10000 reviews
8.5Crew
8.1Boarding
7.1Entertainment
7.8Comfort
7.1Food
Airline reviews

Very nice as always. Not that it’s anyone’s fault really but for some reason the seat (16C) was really hard…. Not typical for your planes… dunno what or why… maybe it was just me ?, The flight was great otherwise

10.0 ExcellentLee, Jul 2025ORD - SEA
Read more Alaska Airlines reviews

Very nice as always. Not that it’s anyone’s fault really but for some reason the seat (16C) was really hard…. Not typical for your planes… dunno what or why… maybe it was just me ?, The flight was great otherwise

Tickets we booked together in January became two different connecting flights. VERY PISSED a about this and a terrible start to our bucket list vacation

Could not check in online - had to get boarding passes at the ticket counter and our daughter got bumped off our connecting flight. NOT OK!

would have been nice for flight to not be delayed by 2 hours so that we had to pay $80 to get home since BART had shut down. i thought a 10pm arrival would leave enough time to account for delays but i was wrong.

I needed more space to sleep on an overnight flight.

Our flight time was drastically changed which caused us to lose a day of vacation

10 hour delay. Fuel spill. Crew had to drive to Indianapolis to a get a plane. The longest day of travel ever. Poor service.Little to no communication.

Wonderful respectful staff for a short flight late at night...lots of considerations all met!

Flight was delayed which led to missed connection, but rebooked on a more direct flight at the last minute and arrived in Juneau on time with all our luggage. Little stressful and our family seating got split, but it all worked out in the end.

Only issue was the 2 hr delay after an 8 hr layover. Very long day.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Food was surprisingly good but the WiFi was not great

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

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