$237 Find Cheap Flights from The Big Island to Chicago - 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 Chicago departing on 9/16. 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

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Flight Deals

Cheap Flights from The Big Island to Chicago

 
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 Chicago 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 Chicago

Tue, Sep 1 - Tue, Sep 8
Delta Logo
10:05 pm - 3:51 pm
KOA
-
ORD
12h 46m
1 stop
Delta Logo
7:00 am - 5:31 pm
ORD
-
KOA
15h 31m
1 stop
$454Delta
Wed, Sep 9 - Sun, Sep 13
Delta Logo
8:55 pm - 6:01 pm
KOA
-
ORD
16h 06m
1 stop
Delta Logo
7:00 am - 5:31 pm
ORD
-
KOA
15h 31m
1 stop
$454Delta
Tue, Sep 1 - Tue, Sep 8
Delta Logo
10:05 pm - 6:19 pm
KOA
-
ORD
15h 14m
2 stops
Delta Logo
7:00 am - 5:31 pm
ORD
-
KOA
15h 31m
1 stop
$460Delta
Wed, Sep 9 - Sun, Sep 13
Alaska Airlines Logo
10:35 am - 1:22 pm
KOA
-
ORD
21h 47m
1 stop
Alaska Airlines Logo
7:20 am - 2:48 pm
ORD
-
KOA
12h 28m
1 stop
$474Alaska Airlines
Tue, Sep 8 - Sun, Sep 13
American Airlines Logo
3:35 pm - 2:20 pm
KOA
-
ORD
17h 45m
1 stop
American Airlines Logo
5:00 am - 2:03 pm
ORD
-
KOA
14h 03m
1 stop
$512American Airlines
Wed, Sep 9 - Sun, Sep 13
American Airlines Logo
9:45 pm - 6:03 pm
KOA
-
ORD
15h 18m
1 stop
American Airlines Logo
6:00 am - 4:00 pm
ORD
-
KOA
15h 00m
2 stops
$517American Airlines
Tue, Sep 1 - Tue, Sep 8
American Airlines Logo
9:45 pm - 3:55 pm
KOA
-
ORD
13h 10m
2 stops
American Airlines Logo
6:00 am - 4:15 pm
ORD
-
KOA
15h 15m
2 stops
$580American Airlines
Tue, Oct 27 - Wed, Oct 28
United Airlines Logo
12:04 pm - 7:13 am
KOA
-
ORD
14h 09m
1 stop
United Airlines Logo
9:57 pm - 7:32 pm
ORD
-
KOA
26h 35m
1 stop
$752United Airlines
Tue, Oct 27 - Wed, Oct 28
United Airlines Logo
12:04 pm - 7:13 am
KOA
-
ORD
14h 09m
1 stop
United Airlines Logo
9:57 pm - 10:49 am
ORD
-
KOA
17h 52m
1 stop
$772United Airlines
Sun, Aug 16 - Thu, Aug 20
United Airlines Logo
10:50 pm - 2:50 pm
KOA
-
ORD
11h 00m
1 stop
United Airlines Logo
10:55 am - 7:35 pm
ORD
-
KOA
13h 40m
2 stops
$970United Airlines
Useful Info

Good to know

Low season

February

Cheapest flight

$237
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 24% increase in price.
Flight from Kailua-Kona to Chicago O'Hare Airport

FAQs for booking flights from The Big Island to Chicago

  • 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.
7.4
United AirlinesOverall score based on 10061 reviews
7.3Comfort
8.1Crew
6.6Food
7.7Boarding
7.1Entertainment
Airline reviews

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

4.0 OkayN, Jul 2026
PHL - ORD
Read more United Airlines reviews

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

The flight did not have its customary snacks during the flight. Apparently they were never loaded on the plane.

Charging and entertainment didn't work. The meal was horrible. They only came by with the drink cart one time for the 8 hour flight. They did come by with water a couple times.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Munster
Schererville
Chesterton
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to The Big Island

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.