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Cheap flights from Kailua-Kona to Chicago from $224

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 9/17. 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 (KOA-ORD)

Cheap round-trip flights

Alaska Airlines Logo
12:09 pm - 6:59 pmKOA-ORD
26h 50m1 stop
Alaska Airlines Logo
2:54 pm - 2:43 pmORD-KOA
27h 49m1 stop
$446Alaska Airlines
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Mon, Nov 10 - Mon, Nov 17
Delta Logo
9:30 pm - 1:20 pmKOA-ORD
10h 50m1 stop
Delta Logo
7:10 am - 5:29 pmORD-KOA
15h 19m1 stop
$447Delta
Find Deal
Thu, Sep 25 - Tue, Sep 30
Alaska Airlines Logo
12:09 pm - 6:59 pmKOA-ORD
26h 50m1 stop
Alaska Airlines Logo
9:20 am - 8:27 pmORD-KOA
15h 07m2 stops
$451Alaska Airlines
Find Deal
Mon, Nov 10 - Mon, Nov 17
Alaska Airlines Logo
12:16 pm - 5:00 amKOA-ORD
11h 44m1 stop
Alaska Airlines Logo
1:01 pm - 10:13 pmORD-KOA
14h 12m2 stops
$452Alaska Airlines
Find Deal
Thu, Sep 18 - Tue, Sep 30
Delta Logo
9:30 pm - 1:20 pmKOA-ORD
10h 50m1 stop
Delta Logo
7:10 am - 5:29 pmORD-KOA
15h 19m1 stop
$456Delta
Find Deal
Sat, Sep 20 - Tue, Sep 30
Logo
8:10 am - 9:32 pmKOA-ORD
32h 22m2 stops
Logo
1:01 pm - 10:09 pmORD-KOA
14h 08m1 stop
$610
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Thu, Sep 4 - Mon, Sep 8
Southwest Logo
8:30 pm - 2:25 pmKOA-ORD
12h 55m1 stop
Southwest Logo
6:15 am - 12:10 pmORD-KOA
10h 55m1 stop
$623Southwest
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Thu, Sep 4 - Mon, Sep 8
United Airlines Logo
11:00 pm - 8:25 pmKOA-ORD
16h 25m2 stops
United Airlines Logo
7:47 pm - 11:26 amORD-KOA
20h 39m2 stops
$627United Airlines
Find Deal
Tue, Sep 23 - Wed, Oct 1
Hawaiian Airlines Logo
8:00 am - 11:59 pmKOA-ORD
10h 59m1 stop
Hawaiian Airlines Logo
5:59 pm - 9:40 pmORD-KOA
32h 41m1 stop
$630Hawaiian Airlines
Find Deal
Sat, Oct 4 - Sat, Oct 11
Southwest Logo
8:30 pm - 4:45 pmKOA-ORD
15h 15m2 stops
Southwest Logo
6:15 am - 6:10 pmORD-KOA
16h 55m2 stops
$634Southwest
Find Deal
Thu, Sep 4 - Mon, Sep 8

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

Our best Delta deals on Kailua-Kona to Chicago O'Hare Intl Airport flight tickets
Delta
Sep 25
KOA9:30 pmKona Intl
10h 50m
1 stop
ORD1:20 pmChicago O'Hare Intl
Sep 30
ORD7:10 amChicago O'Hare Intl
15h 19m
1 stop
KOA5:29 pmKona Intl
$447
Find similar
Delta
Sep 20
KOA9:30 pmKona Intl
10h 50m
1 stop
ORD1:20 pmChicago O'Hare Intl
Sep 30
ORD7:10 amChicago O'Hare Intl
15h 19m
1 stop
KOA5:29 pmKona Intl
$456
Find similar
Delta
Sep 20
KOA9:30 pmKona Intl
10h 50m
1 stop
ORD1:20 pmChicago O'Hare Intl
Sep 28
ORD7:10 amChicago O'Hare Intl
15h 19m
1 stop
KOA5:29 pmKona Intl
$465
Find similar

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

Our best United Airlines deals on Kailua-Kona to Chicago O'Hare Intl Airport flight tickets
United Airlines
Sep 23
KOA11:00 pmKona Intl
16h 25m
2 stops
ORD8:25 pmChicago O'Hare Intl
Oct 1
ORD7:47 pmChicago O'Hare Intl
20h 39m
2 stops
KOA11:26 amKona Intl
$627
Find similar
United Airlines
Aug 24
KOA7:40 pmKona Intl
16h 25m
2 stops
ORD5:05 pmChicago O'Hare Intl
Aug 31
ORD10:49 amChicago O'Hare Intl
13h 35m
1 stop
KOA7:24 pmKona Intl
$832
Find similar
United Airlines
Aug 25
KOA7:40 pmKona Intl
12h 35m
2 stops
ORD1:15 pmChicago O'Hare Intl
Aug 30
ORD9:30 amChicago O'Hare Intl
12h 13m
1 stop
KOA4:43 pmKona Intl
$940
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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 August 21, 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

Mon 11/10

12:09 pm-6:59 pm

1 stop26h 50m

Chicago O'Hare Intl

Mon 11/17

2:54 pm-2:43 pm

1 stop27h 49m

$446

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 9/25

9:30 pm-1:20 pm

1 stop10h 50m

Chicago O'Hare Intl

Tue 9/30

7:10 am-5:29 pm

1 stop15h 19m

$447

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 11/10

12:09 pm-6:59 pm

1 stop26h 50m

Chicago O'Hare Intl

Mon 11/17

9:20 am-8:27 pm

2 stops15h 07m

$451

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 9/18

12:16 pm-5:00 am

1 stop11h 44m

Chicago O'Hare Intl

Tue 9/30

1:01 pm-10:13 pm

2 stops14h 12m

$452

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 9/20

9:30 pm-1:20 pm

1 stop10h 50m

Chicago O'Hare Intl

Tue 9/30

7:10 am-5:29 pm

1 stop15h 19m

$456

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 9/4

8:10 am-9:32 pm

2 stops32h 22m

Chicago O'Hare Intl

Mon 9/8

1:01 pm-10:09 pm

1 stop14h 08m

$610

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 9/4

8:30 pm-2:25 pm

1 stop12h 55m

Chicago O'Hare Intl

Mon 9/8

6:15 am-12:10 pm

1 stop10h 55m

$623

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 9/23

11:00 pm-8:25 pm

2 stops16h 25m

Chicago O'Hare Intl

Wed 10/1

7:47 pm-11:26 am

2 stops20h 39m

$627

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 10/4

8:00 am-11:59 pm

1 stop10h 59m

Chicago O'Hare Intl

Sat 10/11

5:59 pm-9:40 pm

1 stop32h 41m

$630

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 9/4

8:30 pm-4:45 pm

2 stops15h 15m

Chicago O'Hare Intl

Mon 9/8

6:15 am-6:10 pm

2 stops16h 55m

$634

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 September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Kailua-Kona averaging around $503.

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 $1,135.

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 $1,066. 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 3 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 August 2025, prices for Kailua-Kona to Chicago O'Hare Intl Airport flights are approximately 26% more expensive 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 55m

Direct flights

Sun
The fastest flight from Kailua-Kona to Chicago O'Hare Intl Airport takes 7h 55m
Direct flights go from Kailua-Kona to Chicago O'Hare Intl Airport on Sunday. There are no airlines offering direct flights.
Search flight deals

  • 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 30m 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
American AirlinesPriceFrom $399Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $429Free CancellationRating
7.4
8,930 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $507Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights

Traveling to a place near Chicago?

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