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Cheap flights from Kailua-Kona to Chicago from $192

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Kailua-Kona to Chicago departing on 2/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Kailua-Kona to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Hawaiian Airlines Logo
9:10 pm - 2:38 pmKOA-ORD
13h 28m1 stop
Hawaiian Airlines Logo
8:00 am - 9:30 pmORD-KOA
17h 30m1 stop
$382Hawaiian Airlines
Find Deal
Thu, Jan 29 - Mon, Feb 2
Alaska Airlines Logo
6:00 am - 11:37 pmKOA-ORD
13h 37m2 stops
Alaska Airlines Logo
3:44 pm - 3:27 pmORD-KOA
27h 43m1 stop
$402Alaska Airlines
Find Deal
Thu, Jan 29 - Mon, Feb 2
Alaska Airlines Logo
2:24 pm - 11:37 pmKOA-ORD
29h 13m1 stop
Alaska Airlines Logo
9:00 am - 6:26 amORD-KOA
25h 26m2 stops
$407Alaska Airlines
Find Deal
Mon, Jan 19 - Thu, Jan 22
Alaska Airlines Logo
2:24 pm - 11:37 pmKOA-ORD
29h 13m1 stop
Alaska Airlines Logo
8:00 am - 9:30 pmORD-KOA
17h 30m1 stop
$411Alaska Airlines
Find Deal
Mon, Jan 19 - Thu, Jan 22
Delta Logo
8:45 pm - 4:57 pmKOA-ORD
16h 12m2 stops
Delta Logo
7:30 am - 6:30 pmORD-KOA
15h 00m2 stops
$444Delta
Find Deal
Mon, Jan 19 - Thu, Jan 22
Delta Logo
9:30 pm - 4:38 pmKOA-ORD
15h 08m2 stops
Delta Logo
7:30 am - 7:10 pmORD-KOA
15h 40m2 stops
$517Delta
Find Deal
Thu, Jan 29 - Mon, Feb 2
Alaska Airlines Logo
9:10 pm - 4:55 pmKOA-ORD
15h 45m1 stop
Alaska Airlines Logo
3:05 pm - 10:40 amORD-KOA
23h 35m2 stops
$592Alaska Airlines
Find Deal
Sat, Dec 6 - Wed, Dec 10
Alaska Airlines Logo
5:00 pm - 2:09 pmKOA-ORD
17h 09m2 stops
Alaska Airlines Logo
3:05 pm - 10:40 amORD-KOA
23h 35m2 stops
$597Alaska Airlines
Find Deal
Sat, Dec 6 - Wed, Dec 10
Alaska Airlines Logo
1:00 pm - 6:21 amKOA-ORD
13h 21m1 stop
Alaska Airlines Logo
3:05 pm - 4:00 pmORD-KOA
28h 55m1 stop
$665Alaska Airlines
Find Deal
Sat, Dec 6 - Wed, Dec 10
Alaska Airlines Logo
1:00 pm - 6:21 amKOA-ORD
13h 21m1 stop
Alaska Airlines Logo
8:55 am - 4:00 pmORD-KOA
11h 05m1 stop
$698Alaska Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7

Hawaiian Airlines flights from Kailua-Kona to Chicago O'Hare Intl Airport

Our best Hawaiian Airlines deals on Kailua-Kona to Chicago O'Hare Intl Airport flight tickets
Hawaiian Airlines
Jan 29
KOA9:10 pmKona Intl
16h 00m
1 stop
ORD5:10 pmChicago O'Hare Intl
Feb 2
ORD8:00 amChicago O'Hare Intl
17h 30m
1 stop
KOA9:30 pmKona Intl
$382
Find similar
Hawaiian Airlines
Dec 11
KOA9:00 amKona Intl
10h 59m
1 stop
ORD11:59 pmChicago O'Hare Intl
Dec 20
ORD8:58 pmChicago O'Hare Intl
23h 07m
1 stop
KOA4:05 pmKona Intl
$1,084
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Alaska Airlines flights from Kailua-Kona to Chicago O'Hare Intl Airport

Our best Alaska Airlines deals on Kailua-Kona to Chicago O'Hare Intl Airport flight tickets
Alaska Airlines
Jan 29
KOA6:38 pmKona Intl
15h 51m
2 stops
ORD2:29 pmChicago O'Hare Intl
Feb 2
ORD6:06 pmChicago O'Hare Intl
31h 24m
1 stop
KOA9:30 pmKona Intl
$402
Find similar
Alaska Airlines
Jan 19
KOA2:24 pmKona Intl
29h 13m
1 stop
ORD11:37 pmChicago O'Hare Intl
Jan 22
ORD9:00 amChicago O'Hare Intl
25h 26m
2 stops
KOA6:26 amKona Intl
$407
Find similar
Alaska Airlines
Jan 19
KOA2:24 pmKona Intl
29h 13m
1 stop
ORD11:37 pmChicago O'Hare Intl
Jan 22
ORD8:00 amChicago O'Hare Intl
17h 30m
1 stop
KOA9:30 pmKona Intl
$411
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Kailua-Kona to Chicago O'Hare Intl Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 24, 2025.
Use the filters below to find and compare flights from Kailua-Kona to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 1/29

9:10 pm-2:38 pm

1 stop13h 28m

Chicago O'Hare Intl

Mon 2/2

8:00 am-9:30 pm

1 stop17h 30m

$382

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 1/29

6:00 am-11:37 pm

2 stops13h 37m

Chicago O'Hare Intl

Mon 2/2

3:44 pm-3:27 pm

1 stop27h 43m

$402

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 1/19

2:24 pm-11:37 pm

1 stop29h 13m

Chicago O'Hare Intl

Thu 1/22

9:00 am-6:26 am

2 stops25h 26m

$407

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 1/19

2:24 pm-11:37 pm

1 stop29h 13m

Chicago O'Hare Intl

Thu 1/22

8:00 am-9:30 pm

1 stop17h 30m

$411

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 1/19

8:45 pm-4:57 pm

2 stops16h 12m

Chicago O'Hare Intl

Thu 1/22

7:30 am-6:30 pm

2 stops15h 00m

$444

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 1/29

9:30 pm-4:38 pm

2 stops15h 08m

Chicago O'Hare Intl

Mon 2/2

7:30 am-7:10 pm

2 stops15h 40m

$517

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 12/6

9:10 pm-4:55 pm

1 stop15h 45m

Chicago O'Hare Intl

Wed 12/10

3:05 pm-10:40 am

2 stops23h 35m

$592

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 12/6

5:00 pm-2:09 pm

2 stops17h 09m

Chicago O'Hare Intl

Wed 12/10

3:05 pm-10:40 am

2 stops23h 35m

$597

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 12/6

1:00 pm-6:21 am

1 stop13h 21m

Chicago O'Hare Intl

Wed 12/10

3:05 pm-4:00 pm

1 stop28h 55m

$665

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 12/4

1:00 pm-6:21 am

1 stop13h 21m

Chicago O'Hare Intl

Sun 12/7

8:55 am-4:00 pm

1 stop11h 05m

$698

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Kailua-Kona to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Kailua-Kona averaging around $567.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Monday when prices can be found for as low as $484. This is often the case because there is less demand to fly during this day of the week. On the other hand, Saturday is the most expensive day to depart from Kailua-Kona because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,188.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Kailua-Kona in the morning is the least expensive time of day to depart. momondo users have found prices as low as $251 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $1,188. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Kona Intl to Chicago O'Hare Intl flight route?

Fly from Kona Intl to Chicago O'Hare Intl for the best Kona Intl - Chicago O'Hare Intl flight prices

What cabin class options are available on Kona Intl to Chicago O'Hare Intl flights?

There are 2 cabin classes available to choose from on Kona Intl to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Kailua-Kona to Chicago O'Hare Intl Airport flight prices changed over time?

As of November 2025, prices for Kailua-Kona to Chicago O'Hare Intl Airport flights are approximately 18% cheaper when compared to flights at the same time last year.

When to book flights from Kailua-Kona to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Kailua-Kona to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Kailua-Kona to Chicago O'Hare Intl Airport (KOA to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Kailua-Kona to Chicago O'Hare Intl Airport

Fastest flight time

7h 58m

Direct flights

Sun
The fastest flight from Kailua-Kona to Chicago O'Hare Intl Airport takes 7h 58m
Direct flights go from Kailua-Kona to Chicago O'Hare Intl Airport on Sunday. There are no airlines offering direct flights.
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  • How far is Kona Intl to Chicago O'Hare Intl by plane?

    The distance between Kona Intl and Chicago O'Hare Intl is about 4205.9 mi. Typically, this will take 10h 34m by plane in normal conditions.

  • When did momondo last update prices for flights from Kona Intl Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Kona Intl Airport to Chicago O'Hare Intl Airport are updated daily.

  • How many operators does momondo search for flights from Kona Intl Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Kona Intl Airport to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Kona Intl Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Kailua-Kona to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Kailua-Kona to Chicago O'Hare Intl Airport?

Best airlines flying from Kailua-Kona to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Kailua-Kona to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $447Free CancellationRating
7.4
9,036 reviews
Search United Airlines flights
American AirlinesPriceFrom $545Free CancellationRating
7.2
11,046 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Tinley Park
Janesville
Aurora
Elgin
Benton Harbor

Why use momondo?

Why should I use momondo to find a flight deal from Kailua-Kona to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Kailua-Kona to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Kailua-Kona to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Kailua-Kona which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Kailua-Kona to Chicago?

Once you have performed a search for Kailua-Kona to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Kailua-Kona to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Kailua-Kona are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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