ORD

$235 Find Cheap Flights from The Big Island to Chicago - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Useful Info
Flight Deals

Cheap Flights from The Big Island to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from The Big Island to Chicago

Wed, Nov 11 - Mon, Nov 16
Alaska Airlines Logo
11:34 am - 1:17 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
21h 43m1 stop San Diego
Alaska Airlines Logo
2:15 pm - 3:52 pmORD  Chicago O'Hare Intl-KOA Kona Intl
29h 37m1 stop San Diego
$470Alaska Airlines
Wed, Nov 11 - Mon, Nov 16
Multiple Airlines Logo
7:15 pm - 6:59 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
19h 44m2 stops Honolulu San Diego
Multiple Airlines Logo
2:15 pm - 3:52 pmORD  Chicago O'Hare Intl-KOA Kona Intl
29h 37m1 stop San Diego
$475Multiple Airlines
Wed, Nov 11 - Mon, Nov 16
Multiple Airlines Logo
7:15 pm - 6:59 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
19h 44m2 stops Honolulu San Diego
Multiple Airlines Logo
7:57 pm - 2:08 pmORD  Chicago O'Hare Intl-KOA Kona Intl
22h 11m2 stops San Diego Honolulu
$481Multiple Airlines
Wed, Nov 11 - Mon, Nov 16
Delta Logo
8:55 pm - 12:03 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
11h 08m1 stop Salt Lake City
Delta Logo
7:35 am - 3:00 pmORD  Chicago O'Hare Intl-KOA Kona Intl
11h 25m1 stop Salt Lake City
$490Delta
Wed, Nov 11 - Mon, Nov 16
Multiple Airlines Logo
8:45 pm - 6:59 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
18h 14m2 stops Honolulu San Diego
Multiple Airlines Logo
7:57 pm - 3:52 pmORD  Chicago O'Hare Intl-KOA Kona Intl
23h 55m1 stop San Diego
$495Multiple Airlines
Wed, Nov 11 - Mon, Nov 16
Multiple Airlines Logo
8:45 pm - 6:59 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
18h 14m2 stops Honolulu San Diego
Multiple Airlines Logo
7:57 pm - 2:08 pmORD  Chicago O'Hare Intl-KOA Kona Intl
22h 11m2 stops San Diego Honolulu
$501Multiple Airlines
Tue, Nov 17 - Tue, Nov 24
Delta Logo
10:40 pm - 1:37 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
10h 57m1 stop Seattle/Tacoma Intl
Delta Logo
6:40 am - 7:25 pmORD  Chicago O'Hare Intl-KOA Kona Intl
16h 45m1 stop Seattle/Tacoma Intl
$562Delta
Mon, Nov 16 - Tue, Nov 24
Delta Logo
8:55 pm - 12:03 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
11h 08m1 stop Salt Lake City
Delta Logo
6:40 am - 7:25 pmORD  Chicago O'Hare Intl-KOA Kona Intl
16h 45m1 stop Seattle/Tacoma Intl
$562Delta
Thu, Oct 22 - Tue, Nov 10
American Airlines Logo
9:45 pm - 12:59 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
10h 14m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
6:50 am - 3:02 pmORD  Chicago O'Hare Intl-KOA Kona Intl
12h 12m1 stop Phoenix Sky Harbor Intl
$636American Airlines
Wed, Nov 25 - Sun, Nov 29
American Airlines Logo
10:09 pm - 3:00 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
12h 51m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
8:48 pm - 3:02 pmORD  Chicago O'Hare Intl-KOA Kona Intl
22h 14m1 stop Phoenix Sky Harbor Intl
$694American Airlines
Useful Info

Good to know

Low season

January

Cheapest flight

$235
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Kailua-Kona to Chicago O'Hare Airport

FAQs for booking The Big Island to Chicago flights

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

    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.

  • 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?

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

    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 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?

    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 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 airline flying from The Big Island to Chicago

 
Need help choosing which airline to fly with from The Big Island to Chicago? 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.
7.1
American AirlinesOverall score based on 12061 reviews
7.4Boarding
6.8Entertainment
7.9Crew
7.2Comfort
6.4Food
Airline reviews

We were stuck with no gate upon landing for 90 minutes. Unacceptable.

2.0 MediocreKatherine, Sep 2026
Read more American Airlines reviews

We were stuck with no gate upon landing for 90 minutes. Unacceptable.

Horrible. Flight was delayed for 4 hours first till 7pm. Then for one more hour. Then again and around 9pm we were finally boarded and waited for catering delivery for another hour. At 10pm we were not interested on food at all. Tired, sleepy we arrived after midnight. Insane.

I've never seen such poor lack of information at a gate station in 69 years. The flight from COS was to depart at 12:37pm. At boarding time, the gate agent in the microphone mumbled something completely unintelligible. I understood one word. "mechanical". Nothing else. Absolutely nothing else was reported for the next 1-1/2 hours. Past the time for departure, at 12:37pm, the gate agent simply walked away and the station was left unattended, as all of the passengers waited expectantly. The board still said that the flight was ON TIME. That was hard to believe since it was then well past 12:37pm and we all were sitting at the gate and there was absolutely no gate agent anywhere in site. I stopped an employee who was standing somewhere else and said that we can use some information. Much later, the same gate agent said that he will have information for us about 5 minutes but he "doesn't know any more than you do." Of course, five minutes came and went and he did absolutely nothing. One and a half hours after 12:37pm, he opened the door and began boarding. No explanation, no apology. Once we were boarded, the same happened on the plane. We sat. No explanation, no apology, from any flight attendants. Finally, finally, a pilot apologized and explained that there would be a delay. WELL NO KIDDING !

Our flight from Chicago to Des Moines was the problem flight due to a dismissive flight attendant. His conduct was unnecessary and unprofessional.. I will avoid using Americam Airlines again because of the situation. Very disappointing.

Mostly excellent. However, many too many gate changes. Connecting flight at ORD changed gate 6 times.

Mechanical issues and delays. I get it but bad experience. Turned my 3 hour airport experience into a 9 hours

The baggage process at the gate was terrible. Stay was not friendly at all

Flight was delayed because of mechanical. Could not get landing space which caused me to miss my connection. Messy and not organized.

We landed slightly early but then sat in holding area waiting for our gate to clear out for about an hour, so technically we arrived one hour late at the gate at ORD. The airport may be partially responsible here, but regardless of who is responsible, it was a bad experience to be so close yet unable to get off the plane.

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Gurnee
South Haven
Oak Brook
Tinley Park
Hammond
Saint Joseph
Des Plaines
Elk Grove Village
Hoffman Estates
Portage
South Holland
Oakbrook Terrace
Willowbrook
Lansing
Alsip
Delavan
Lisle
Northbrook
Valparaiso

More options for your flight to Chicago