$217 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 3/7. 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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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-Kona2 stops$408
Hilo
Hilo2 stops$455
Kailua-Kona
Kailua-Kona2 stops$408
Hilo
Hilo2 stops$455

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, Mar 10 - Tue, Mar 17
Multiple Airlines Logo
8:20 am - 8:27 pm
ORD
-
KOA
17h 07m
2 stops
Multiple Airlines Logo
12:10 pm - 7:02 pm
KOA
-
ORD
25h 52m
1 stop
$408Multiple Airlines
Tue, May 5 - Wed, May 13
Alaska Airlines Logo
3:52 pm - 2:56 pm
ORD
-
KOA
28h 04m
1 stop
Alaska Airlines Logo
8:00 am - 11:59 pm
KOA
-
ORD
10h 59m
1 stop
$412Alaska Airlines
Tue, Mar 3 - Tue, Mar 10
Multiple Airlines Logo
7:00 am - 5:13 pm
ORD
-
KOA
14h 13m
1 stop
Multiple Airlines Logo
2:41 pm - 2:58 pm
KOA
-
ORD
19h 17m
2 stops
$413Multiple Airlines
Tue, Feb 24 - Tue, Mar 3
Multiple Airlines Logo
8:20 am - 10:15 pm
ORD
-
KOA
17h 55m
2 stops
Multiple Airlines Logo
3:37 pm - 2:58 pm
KOA
-
ORD
19h 21m
2 stops
$415Multiple Airlines
Tue, Feb 24 - Tue, Mar 3
Multiple Airlines Logo
7:00 am - 5:13 pm
ORD
-
KOA
14h 13m
1 stop
Multiple Airlines Logo
9:01 pm - 2:58 pm
KOA
-
ORD
13h 57m
2 stops
$417Multiple Airlines
Tue, Feb 24 - Tue, Mar 3
American Airlines Logo
5:00 am - 3:30 pm
ORD
-
KOA
14h 30m
1 stop
American Airlines Logo
10:11 pm - 1:33 pm
KOA
-
ORD
11h 22m
1 stop
$422American Airlines
Tue, Feb 24 - Tue, Mar 3
Delta Logo
9:34 am - 7:39 pm
MDW
-
KOA
14h 05m
2 stops
Delta Logo
10:55 pm - 6:40 pm
KOA
-
MDW
15h 45m
2 stops
$462Delta
Tue, Mar 3 - Tue, Mar 10
Delta Logo
9:34 am - 7:39 pm
MDW
-
KOA
14h 05m
2 stops
Delta Logo
10:15 pm - 5:54 pm
KOA
-
MDW
14h 39m
2 stops
$465Delta
Wed, Mar 4 - Wed, Mar 18
Southwest Logo
6:10 am - 1:45 pm
MDW
-
KOA
11h 35m
1 stop
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m
1 stop
$481Southwest
Wed, Mar 4 - Wed, Mar 18
Southwest Logo
6:10 am - 1:45 pm
MDW
-
KOA
11h 35m
1 stop
Southwest Logo
10:00 am - 5:00 am
KOA
-
MDW
14h 00m
2 stops
$501Southwest
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 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 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 $412, 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 September, when tickets cost $591 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $1,073 and $953 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$217
Best time to beat the crowds with an average 19% 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.

  • 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 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.
8.0
Alaska AirlinesOverall score based on 11819 reviews
7.0Entertainment
8.5Crew
7.1Food
8.1Boarding
7.8Comfort
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.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

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.

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

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.

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

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.