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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

$233 CHEAP FLIGHTS from The Big Island to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

...and more

Travelers love KAYAK

41,299,237 searches in the past 7 days on KAYAK

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Filter your dealsChoose cabin class, free Wi-Fi and more.

Cheapest round-trip

$399

Overall average: $705

Alaska Airlines

Tue 3/3Wed 3/4

KOA - ORD • 2 stops

Cheapest one-way

$233

Typical prices: $239-$298

Alaska Airlines

Sun 11/23

KOA - ORD • 1 stop

Start a new search

KAYAK searches 100s of sites at once to find you the best travel deals.

We hope you love your trip to Chicago!

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.

Round-trip

One-way

Last minute

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

Tue, Mar 3 - Wed, Mar 4

6:00 am - 11:10 pmKOA-ORD

13h 10m2 stops

2:59 pm - 2:46 pmORD-KOA

27h 47m1 stop

$399Alaska Airlines

Find Deal

Tue, Mar 3 - Wed, Mar 4

12:00 pm - 1:59 pmKOA-ORD

21h 59m1 stop

6:50 pm - 10:35 pmORD-KOA

31h 45m1 stop

$433Alaska Airlines

Find Deal

Tue, Mar 3 - Wed, Mar 4

6:00 am - 11:10 pmKOA-ORD

13h 10m2 stops

9:00 am - 7:25 pmORD-KOA

14h 25m2 stops

$436Alaska Airlines

Find Deal

Sun, Feb 1 - Fri, Feb 6

6:00 am - 11:37 pmITO-ORD

13h 37m2 stops

3:49 pm - 4:13 pmORD-ITO

28h 24m2 stops

$520Alaska Airlines

Find Deal

Tue, Dec 23 - Sat, Dec 27

2:23 pm - 4:37 amKOA-ORD

10h 14m1 stop

9:05 pm - 8:36 pmORD-KOA

27h 31m1 stop

$824United Airlines

Find Deal

Tue, Dec 23 - Sat, Dec 27

11:20 pm - 4:59 pmKOA-ORD

13h 39m2 stops

9:05 pm - 8:36 pmORD-KOA

27h 31m1 stop

$834United Airlines

Find Deal

Tue, Dec 23 - Sat, Dec 27

10:55 pm - 2:24 pmKOA-ORD

11h 29m1 stop

10:40 am - 6:51 pmORD-KOA

12h 11m1 stop

$954American Airlines

Find Deal

Sun, Mar 29 - Sat, Apr 4

9:00 pm - 2:21 pmKOA-ORD

12h 21m1 stop

7:00 am - 9:27 pmORD-KOA

19h 27m2 stops

$1,059Multiple Airlines

Find Deal

Sun, Mar 29 - Sat, Apr 4

9:40 pm - 3:55 pmKOA-ORD

13h 15m1 stop

6:00 am - 2:12 pmORD-KOA

13h 12m1 stop

$1,063American Airlines

Find Deal

Tue, Dec 23 - Sat, Dec 27

10:55 pm - 5:19 pmKOA-MDW

14h 24m2 stops

6:00 am - 8:27 pmMDW-KOA

18h 27m2 stops

$1,420Delta

Find Deal

Useful Info

Low season	January
High season	November
Cheapest flight	$233

Best time to beat the crowds with an average 11% drop in price.

Most popular time to fly with an average 1% increase in price.

Flight from Kailua-Kona to Chicago O'Hare Airport

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.

Merrillville

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Chesterton

Schererville

Munster

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

Cabin class

Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to The Big Island

First Class flights to Chicagofrom $248

Business Class flights to Chicagofrom $190

Prem Econ Class flights to Chicagofrom $78

Economy Class flights to Chicagofrom $24

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.

$233 Find Cheap Flights from The Big Island to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Everything you should know

Cheap Flights from The Big Island to Chicago

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

Recent one-way flight deals from The Big Island to Chicago

Recent last minute flight deals from The Big Island to Chicago

Good to know

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?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to The Big Island

Complete your trip to Chicago with a hotel stay or car rental

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to The Big Island

Choose which airport to fly into in Chicago

Find deals for your return flight