$257 Find Cheap Flights from Chicago 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 Chicago to The Big Island departing on 8/16. 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, 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 Chicago to The Big Island

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Kailua-Kona
Kailua-Kona1 stop$440
Hilo
Hilo2 stops$525
Kailua-Kona
Kailua-Kona1 stop$440
Hilo
Hilo2 stops$525

Book Cheap Chicago 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 Chicago 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 Chicago to The Big Island

Tue, Nov 3 - Mon, Nov 9
Delta Logo
2:55 pm - 7:39 pm
ORD
-
KOA
32h 44m
1 stop
Delta Logo
9:40 pm - 5:21 pm
KOA
-
ORD
15h 41m
1 stop
$440Delta
Tue, Nov 3 - Tue, Nov 10
Delta Logo
2:55 pm - 7:39 pm
ORD
-
KOA
32h 44m
1 stop
Delta Logo
9:40 pm - 9:34 pm
KOA
-
ORD
19h 54m
2 stops
$446Delta
Wed, Sep 9 - Sun, Sep 20
Delta Logo
6:30 pm - 6:34 pm
ORD
-
KOA
29h 04m
1 stop
Delta Logo
9:55 pm - 5:33 pm
KOA
-
ORD
14h 38m
1 stop
$456Delta
Sat, Oct 31 - Mon, Nov 9
Delta Logo
6:00 am - 6:39 pm
ORD
-
KOA
17h 39m
2 stops
Delta Logo
9:40 pm - 5:21 pm
KOA
-
ORD
15h 41m
1 stop
$461Delta
Mon, Nov 2 - Mon, Nov 9
Delta Logo
7:35 am - 7:39 pm
ORD
-
KOA
16h 04m
1 stop
Delta Logo
9:40 pm - 5:57 pm
KOA
-
ORD
16h 17m
2 stops
$462Delta
Mon, Sep 28 - Mon, Oct 5
Delta Logo
6:15 am - 7:23 pm
ORD
-
KOA
18h 08m
2 stops
Delta Logo
9:55 pm - 9:34 pm
KOA
-
ORD
18h 39m
2 stops
$466Delta
Mon, Aug 24 - Tue, Sep 1
Southwest Logo
6:40 am - 12:40 pm
MDW
-
KOA
11h 00m
1 stop
Southwest Logo
8:35 pm - 11:55 am
KOA
-
MDW
10h 20m
1 stop
$514Southwest
Mon, Aug 24 - Tue, Sep 1
Southwest Logo
6:40 am - 12:40 pm
MDW
-
KOA
11h 00m
1 stop
Southwest Logo
8:35 pm - 2:45 pm
KOA
-
MDW
13h 10m
2 stops
$520Southwest
Tue, Sep 8 - Fri, Sep 18
Multiple Airlines Logo
7:20 am - 7:12 pm
ORD
-
ITO
16h 52m
2 stops
Multiple Airlines Logo
6:00 am - 11:59 pm
ITO
-
ORD
12h 59m
2 stops
$525Multiple Airlines
Mon, Aug 24 - Tue, Sep 1
Southwest Logo
5:40 am - 2:10 pm
MDW
-
KOA
13h 30m
2 stops
Southwest Logo
8:35 pm - 2:45 pm
KOA
-
MDW
13h 10m
2 stops
$526Southwest
Booking Insights

KAYAK's insights & trends for Chicago to The Big Island flights

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

What is the cheapest Chicago 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 found in the last 5 days was to Kailua-Kona, at $1,004 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 5 days was $1,004.

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

The average price for all round-trip flights from Chicago to The Big Island depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to The Big Island is generally in the morning, when round-trip flights cost $1,415 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 $1,415.

Can I save money by flying with a layover from Chicago 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 $468, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago 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 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 to The Big Island is January, when tickets cost $262 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $653 and $632 respectively.

How far in advance should I book a flight from Chicago 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 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 to The Big Island, you should book around 4 weeks before departure, which saves you about 30% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$257
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 14% 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 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 from Chicago 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 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 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 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 to 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 5 airlines serving from Chicago 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 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.
7.9
Alaska AirlinesOverall score based on 12509 reviews
7.8Comfort
7.0Food
8.1Boarding
7.0Entertainment
8.5Crew
Airline reviews

The flight attendant and first class were very friendly, efficient, and wanted to make sure that service was great. Highly recommend this airline.

10.0 ExcellentAnonymous, May 2026
SEA - LIH
Read more Alaska Airlines reviews

The flight attendant and first class were very friendly, efficient, and wanted to make sure that service was great. Highly recommend this airline.

Extremely professional crew there are very friendly and first class. Everything worked well on the plane. Food was to be expected. Drinks were very good. Shout out to Charlie in first class who was an excellent flight attendant.

Comfortable seats, good drinks with lots of water refills, staff was kind and understanding of my disabled mother!

The crew seem untrained and uncertain no one ever checked up on us in our first class cabin. I had to ask for water four times and the lady kept saying she was busy when they weren't really doing anything. Had to walk to the back of the plane to get water for myself. Crew seem new and unexperience. You can tell this by the fumbling they kept making trying to fight. (I miss Hawaiian air.)

Our meal order was screwed up. We had to choose from basic boxes. I was not happy.

You can standby to get on earlier flight if the seat is open.

Thanks for all you do to keep us safe and on time!

Boarding was easy and quick. Staff was very friendly. Service of snacks and drinks by staff was outstanding.

Our flight when we finally got rerouted to a different destination than we were going was fine. But 2 days was taken out of our vacation because our flit was cancelled. We understand mechanical problems and of course don’t want to be on a plane that has mechanical problems.Wish there had been another solution.

I like flying Alaska Airlines. I think the staff are happy, the plane is comfortable, the entertainment reasonable, the food acceptable.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

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

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.