ORD

$258 Find Cheap Flights from The Big Island to Chicago O'Hare Airport - Compare and Save

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 8/11. 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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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

Thu, Sep 24 - Mon, Sep 28
Alaska Airlines Logo
12:38 pm - 6:20 am
KOA
-
ORD
12h 42m
1 stop
Alaska Airlines Logo
7:20 am - 2:48 pm
ORD
-
KOA
12h 28m
1 stop
$514Alaska Airlines
Thu, Sep 24 - Mon, Sep 28
Multiple Airlines Logo
12:38 pm - 6:20 am
KOA
-
ORD
12h 42m
1 stop
Multiple Airlines Logo
7:20 am - 6:17 pm
ORD
-
KOA
15h 57m
2 stops
$520Multiple Airlines
Thu, Sep 24 - Mon, Sep 28
Multiple Airlines Logo
6:30 pm - 2:54 pm
KOA
-
ORD
15h 24m
2 stops
Multiple Airlines Logo
7:20 am - 6:17 pm
ORD
-
KOA
15h 57m
2 stops
$525Multiple Airlines
Wed, Sep 16 - Wed, Sep 30
Multiple Airlines Logo
8:45 pm - 11:59 pm
ITO
-
ORD
22h 14m
2 stops
Multiple Airlines Logo
7:20 am - 7:12 pm
ORD
-
ITO
16h 52m
2 stops
$525Multiple Airlines
Wed, Oct 14 - Mon, Oct 19
Alaska Airlines Logo
10:36 am - 1:25 pm
KOA
-
ORD
21h 49m
1 stop
Alaska Airlines Logo
2:21 pm - 2:46 pm
ORD
-
KOA
29h 25m
1 stop
$554Alaska Airlines
Tue, Nov 3 - Wed, Nov 4
Multiple Airlines Logo
6:00 am - 11:49 pm
KOA
-
ORD
13h 49m
2 stops
Multiple Airlines Logo
7:25 am - 3:52 pm
ORD
-
KOA
12h 27m
1 stop
$560Multiple Airlines
Tue, Nov 3 - Wed, Nov 4
Multiple Airlines Logo
6:00 am - 11:49 pm
KOA
-
ORD
13h 49m
2 stops
Multiple Airlines Logo
7:00 am - 7:33 pm
ORD
-
KOA
16h 33m
2 stops
$565Multiple Airlines
Mon, Oct 26 - Mon, Nov 2
American Airlines Logo
3:45 pm - 7:10 am
ITO
-
ORD
10h 25m
1 stop
American Airlines Logo
10:00 am - 4:59 pm
ORD
-
ITO
10h 59m
1 stop
$769American Airlines
Mon, Oct 26 - Mon, Nov 2
American Airlines Logo
8:45 pm - 4:03 pm
ITO
-
ORD
14h 18m
2 stops
American Airlines Logo
10:00 am - 5:27 pm
ORD
-
ITO
11h 27m
1 stop
$778American Airlines
Wed, Sep 16 - Wed, Sep 30
United Airlines Logo
11:27 am - 5:04 am
ITO
-
ORD
12h 37m
1 stop
United Airlines Logo
9:30 am - 3:13 pm
ORD
-
ITO
10h 43m
1 stop
$883United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$258
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 8% increase in price.
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 3 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.
7.9
SouthwestOverall score based on 4237 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
Airline reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

4.0 OkaySteven, Jun 2026
ONT - LAS
Read more Southwest reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

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

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

Traveling to a place near O'Hare Intl?

Book flights to O'Hare Intl if you plan to visit one of these locations
Gurnee
South Haven
Merrillville
Oak Brook
Saint Joseph
Tinley Park
Hammond
Elk Grove Village
Des Plaines
Hoffman Estates
Portage
Willowbrook
South Holland
Delavan
Lansing
Northbrook
Lisle
Elmhurst
Pleasant Prairie
Alsip

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