$173 Find Cheap Flights from The Big Island to Chicago

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 3/24. 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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Everything you should know

Cheapest round-trip
$416
Overall average: $586
Multiple Airlines
Wed 2/18Wed 2/25
KOA - ORD • 1 stop
Cheapest one-way
$173
Typical prices: $333-$548
Multiple Airlines
Tue 3/24
KOA - ORD • 2 stops
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We hope you love your trip to Chicago!
Flight Deals
Useful Info
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

Wed, Feb 18 - Wed, Feb 25
Multiple Airlines Logo
1:10 pm - 11:59 pm
KOA
-
ORD
30h 49m
1 stop
Multiple Airlines Logo
8:20 am - 10:15 pm
ORD
-
KOA
17h 55m
2 stops
$416Multiple Airlines
Wed, Feb 18 - Wed, Feb 25
American Airlines Logo
6:30 pm - 9:45 am
KOA
-
ORD
11h 15m
1 stop
American Airlines Logo
11:31 am - 6:59 pm
ORD
-
KOA
11h 28m
1 stop
$422American Airlines
Wed, Apr 29 - Mon, May 4
Multiple Airlines Logo
8:00 am - 11:59 pm
KOA
-
ORD
10h 59m
1 stop
Multiple Airlines Logo
8:50 am - 10:16 pm
ORD
-
KOA
18h 26m
2 stops
$428Multiple Airlines
Wed, Feb 18 - Sun, Feb 22
Delta Logo
10:55 pm - 9:52 pm
KOA
-
ORD
18h 57m
2 stops
Delta Logo
7:15 am - 3:51 pm
ORD
-
KOA
12h 36m
1 stop
$430Delta
Wed, Apr 29 - Mon, May 4
Multiple Airlines Logo
9:00 pm - 11:43 pm
KOA
-
ORD
21h 43m
2 stops
Multiple Airlines Logo
8:50 am - 10:16 pm
ORD
-
KOA
18h 26m
2 stops
$433Multiple Airlines
Wed, Feb 18 - Wed, Feb 25
Delta Logo
10:55 pm - 5:37 pm
KOA
-
MDW
14h 42m
2 stops
Delta Logo
9:34 am - 7:39 pm
MDW
-
KOA
14h 05m
2 stops
$462Delta
Wed, Feb 18 - Wed, Feb 25
Delta Logo
10:55 pm - 6:59 pm
KOA
-
ORD
16h 04m
2 stops
Delta Logo
6:30 am - 7:39 pm
ORD
-
KOA
17h 09m
2 stops
$462Delta
Wed, Apr 29 - Mon, May 4
Alaska Airlines Logo
1:16 pm - 1:13 pm
KOA
-
ORD
18h 57m
1 stop
Alaska Airlines Logo
8:48 pm - 1:36 pm
ORD
-
KOA
21h 48m
1 stop
$492Alaska Airlines
Wed, Feb 18 - Wed, Feb 25
Southwest Logo
7:00 pm - 12:10 pm
KOA
-
MDW
13h 10m
2 stops
Southwest Logo
6:10 am - 1:45 pm
MDW
-
KOA
11h 35m
1 stop
$592Southwest
Wed, Feb 18 - Wed, Feb 25
Southwest Logo
9:25 pm - 1:45 pm
KOA
-
MDW
12h 20m
1 stop
Southwest Logo
6:10 am - 1:45 pm
MDW
-
KOA
11h 35m
1 stop
$596Southwest
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$173
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 2% lower on average.
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.

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
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

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.
First Class flights to Chicagofrom $329
Business Class flights to Chicagofrom $242
Premium Economy Class flights to Chicagofrom $182
Economy Class flights to Chicagofrom $50