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Cheap flights from Kailua-Kona to Chicago from $269

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Kailua-Kona to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:00 am - 11:59 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
13h 59m2 stops Honolulu San Diego
Multiple Airlines Logo
7:40 am - 4:50 pmORD  Chicago O'Hare Intl-KOA Kona Intl
13h 10m1 stop San Diego
$544Multiple Airlines
Thu, Feb 4 - Mon, Feb 8
Alaska Airlines Logo
11:29 pm - 2:21 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
10h 52m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
7:40 am - 4:50 pmORD  Chicago O'Hare Intl-KOA Kona Intl
13h 10m1 stop San Diego
$585Alaska Airlines
Thu, Feb 4 - Mon, Feb 8
Multiple Airlines Logo
6:00 am - 11:59 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
13h 59m2 stops Honolulu San Diego
Multiple Airlines Logo
2:13 pm - 12:00 pmORD  Chicago O'Hare Intl-KOA Kona Intl
25h 47m2 stops San Diego San Francisco
$623Multiple Airlines
Thu, Feb 4 - Mon, Feb 8
Multiple Airlines Logo
6:00 am - 11:59 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
13h 59m2 stops Honolulu San Diego
Multiple Airlines Logo
2:13 pm - 12:00 pmORD  Chicago O'Hare Intl-KOA Kona Intl
25h 47m2 stops San Diego San Francisco
$643Multiple Airlines
Thu, Feb 4 - Mon, Feb 8
Delta Logo
8:45 pm - 12:03 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
11h 18m1 stop Salt Lake City
Delta Logo
6:40 am - 7:25 pmORD  Chicago O'Hare Intl-KOA Kona Intl
16h 45m1 stop Seattle/Tacoma Intl
$734Delta
Sat, Nov 14 - Wed, Nov 18
Delta Logo
10:45 pm - 1:37 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
10h 52m1 stop Los Angeles
Delta Logo
7:30 am - 7:25 pmORD  Chicago O'Hare Intl-KOA Kona Intl
15h 55m2 stops Salt Lake City Seattle/Tacoma Intl
$740Delta
Sat, Nov 14 - Wed, Nov 18
Delta Logo
10:45 pm - 6:05 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
15h 20m2 stops Los Angeles Salt Lake City
Delta Logo
7:30 am - 7:25 pmORD  Chicago O'Hare Intl-KOA Kona Intl
15h 55m2 stops Salt Lake City Seattle/Tacoma Intl
$745Delta
Sat, Nov 14 - Wed, Nov 18
American Airlines Logo
9:44 pm - 1:52 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
12h 08m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
9:18 pm - 5:33 pmORD  Chicago O'Hare Intl-KOA Kona Intl
24h 15m1 stop Los Angeles
$943American Airlines
Thu, Dec 24 - Mon, Dec 28
American Airlines Logo
10:52 pm - 1:52 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
11h 00m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
9:18 pm - 5:33 pmORD  Chicago O'Hare Intl-KOA Kona Intl
24h 15m1 stop Los Angeles
$943American Airlines
Mon, Dec 21 - Mon, Dec 28
American Airlines Logo
10:52 pm - 1:52 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
11h 00m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
9:18 pm - 5:33 pmORD  Chicago O'Hare Intl-KOA Kona Intl
24h 15m1 stop Los Angeles
$943American Airlines
Wed, Dec 23 - Mon, Dec 28

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American Airlines flights from Kailua-Kona to Chicago

Our best American Airlines deals on Kailua-Kona to Chicago flight tickets
American Airlines
Dec 21
KOA10:52 pmKona Intl
11h 00m
1 stop
ORD1:52 pmChicago O'Hare Intl
Dec 28
ORD9:18 pmChicago O'Hare Intl
24h 15m
1 stop
KOA5:33 pmKona Intl
$943
American Airlines
Dec 23
KOA4:30 pmKona Intl
13h 30m
2 stops
ORD10:00 amChicago O'Hare Intl
Dec 28
ORD9:18 pmChicago O'Hare Intl
24h 15m
1 stop
KOA5:33 pmKona Intl
$948
American Airlines
Dec 18
KOA9:44 pmKona Intl
12h 59m
1 stop
ORD2:43 pmChicago O'Hare Intl
Dec 28
ORD9:18 pmChicago O'Hare Intl
24h 15m
1 stop
KOA5:33 pmKona Intl
$1,002

United Airlines flights from Kailua-Kona to Chicago

Our best United Airlines deals on Kailua-Kona to Chicago flight tickets
United Airlines
Dec 23
KOA2:20 pmKona Intl
10h 49m
1 stop
ORD5:09 amChicago O'Hare Intl
Dec 24
ORD8:40 amChicago O'Hare Intl
16h 05m
1 stop
KOA8:45 pmKona Intl
$1,071
United Airlines
Dec 22
KOA3:33 pmKona Intl
11h 26m
1 stop
ORD6:59 amChicago O'Hare Intl
Dec 24
ORD6:50 amChicago O'Hare Intl
17h 55m
1 stop
KOA8:45 pmKona Intl
$1,076

momondo Fare Finder

 
Use the filters below to find and compare flights from Kailua-Kona to Chicago that are best for you.

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Route

Depart

Return

Price

Cheapest round-trip

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Thu 2/4

6:00 am-11:59 pm

2 stops13h 59m

Chicago O'Hare Intl

Mon 2/8

7:40 am-4:50 pm

1 stop13h 10m

$544
Quickest round-trip

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Thu 2/4

11:29 pm-2:21 pm

1 stop10h 52m

Chicago O'Hare Intl

Mon 2/8

7:40 am-4:50 pm

1 stop13h 10m

$585

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Thu 2/4

6:00 am-11:59 pm

2 stops13h 59m

Chicago O'Hare Intl

Mon 2/8

2:13 pm-12:00 pm

2 stops25h 47m

$623

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Thu 2/4

6:00 am-11:59 pm

2 stops13h 59m

Chicago O'Hare Intl

Mon 2/8

2:13 pm-12:00 pm

2 stops25h 47m

$643

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Sat 11/14

8:45 pm-12:03 pm

1 stop11h 18m

Chicago O'Hare Intl

Wed 11/18

6:40 am-7:25 pm

1 stop16h 45m

$734

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Sat 11/14

10:45 pm-1:37 pm

1 stop10h 52m

Chicago O'Hare Intl

Wed 11/18

7:30 am-7:25 pm

2 stops15h 55m

$740

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Sat 11/14

10:45 pm-6:05 pm

2 stops15h 20m

Chicago O'Hare Intl

Wed 11/18

7:30 am-7:25 pm

2 stops15h 55m

$745

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Thu 12/24

9:44 pm-1:52 pm

1 stop12h 08m

Chicago O'Hare Intl

Mon 12/28

9:18 pm-5:33 pm

1 stop24h 15m

$943

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Mon 12/21

10:52 pm-1:52 pm

1 stop11h 00m

Chicago O'Hare Intl

Mon 12/28

9:18 pm-5:33 pm

1 stop24h 15m

$943

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Wed 12/23

10:52 pm-1:52 pm

1 stop11h 00m

Chicago O'Hare Intl

Mon 12/28

9:18 pm-5:33 pm

1 stop24h 15m

$943

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Kailua-Kona to Chicago

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?

The month of October is, on average, the cheapest month to fly to Chicago from Kailua-Kona, with most prices found around $570. If you’re not able to fly to Chicago in October, then November is your next best option. Flight prices from Kailua-Kona to Chicago during November average around $616.

What is the cheapest Kona Intl to Chicago flight route?

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

What cabin class options are available on Kailua-Kona to Chicago flights?

There is only 1 cabin class available to choose from on Kailua-Kona to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Kailua-Kona to Chicago flights?

You could potentially save up to 37% on your flight if you consider stops on a Kailua-Kona to Chicago flight.

How have Kailua-Kona to Chicago flight prices changed over time?

As of November 2026, prices for Kailua-Kona to Chicago flights are approximately 23% cheaper when compared to flights at the same time last year.

When to book flights from Kailua-Kona to Chicago

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

Cheap Kailua-Kona to Chicago (KOA to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Kailua-Kona to Chicago

Best Price Found

$269

Fastest flight time

12h 05m

Direct flights

Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Kailua-Kona in the past 72 hours is $269. The best round-trip flight deal from Kailua-Kona to Chicago found on momondo in the last 72 hours is $544.
The fastest flight from Kailua-Kona to Chicago takes 12h 05m
Direct flights go from Kailua-Kona to Chicago on Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Kailua-Kona there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Kailua-Kona to Chicago

  • How far is Kona Intl to Chicago by plane?

    There are 4220.2 mi between Kona Intl and Chicago. A reasonable flight in good conditions will take 12h 05m.

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

    Prices for flights from Kona Intl Airport to Chicago were last updated today.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Kona Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Kailua-Kona to Chicago?

Best airlines flying from Kailua-Kona to Chicago

Compare and see reviews for airlines that fly from Kailua-Kona to Chicago with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $217Free CancellationRating
7.8
8,697 reviews
Search Delta flights
American AirlinesPriceFrom $422Free CancellationRating
7.0
12,230 reviews
Search American Airlines flights

Traveling to a place near Chicago?

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

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Kailua-Kona.

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

Yes. All flights to Chicago from Kailua-Kona on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Kailua-Kona.

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

If you are not ready to book a flight from Kailua-Kona to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport