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Cheap flights from Kailua-Kona to Chicago from $229

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.
Alaska Airlines Logo
11:34 am - 1:17 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
21h 43m1 stop San Diego
Alaska Airlines Logo
2:15 pm - 3:52 pmORD  Chicago O'Hare Intl-KOA Kona Intl
29h 37m1 stop San Diego
$470Alaska Airlines
Thu, Nov 5 - Sat, Nov 14
Delta Logo
9:06 pm - 4:53 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
14h 47m1 stop Seattle/Tacoma Intl
Delta Logo
7:35 am - 3:00 pmORD  Chicago O'Hare Intl-KOA Kona Intl
11h 25m1 stop Salt Lake City
$470Delta
Tue, Oct 27 - Tue, Nov 17
Southwest Logo
11:40 am - 5:55 amKOA  Kona Intl-MDW Chicago Midway
14h 15m2 stops Honolulu Oakland
Southwest Logo
5:20 am - 2:15 pmMDW  Chicago Midway-KOA Kona Intl
12h 55m2 stops Phoenix Sky Harbor Intl Kahului
$470Southwest
Wed, Nov 11 - Mon, Nov 16
Alaska Airlines Logo
11:34 am - 1:17 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
21h 43m1 stop San Diego
Alaska Airlines Logo
2:15 pm - 3:52 pmORD  Chicago O'Hare Intl-KOA Kona Intl
29h 37m1 stop San Diego
$470Alaska Airlines
Wed, Nov 11 - Mon, Nov 16
Multiple Airlines Logo
7:15 pm - 6:59 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
19h 44m2 stops Honolulu San Diego
Multiple Airlines Logo
2:15 pm - 3:52 pmORD  Chicago O'Hare Intl-KOA Kona Intl
29h 37m1 stop San Diego
$475Multiple Airlines
Thu, Nov 5 - Sat, Nov 14
Multiple Airlines Logo
7:15 pm - 6:59 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
19h 44m2 stops Honolulu San Diego
Multiple Airlines Logo
2:15 pm - 3:52 pmORD  Chicago O'Hare Intl-KOA Kona Intl
29h 37m1 stop San Diego
$475Multiple Airlines
Wed, Nov 11 - Mon, Nov 16
Delta Logo
9:06 pm - 1:30 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
11h 24m1 stop Seattle/Tacoma Intl
Delta Logo
6:23 am - 7:25 pmORD  Chicago O'Hare Intl-KOA Kona Intl
17h 02m2 stops Minneapolis St Paul Seattle/Tacoma Intl
$476Delta
Tue, Oct 27 - Tue, Nov 17
Multiple Airlines Logo
7:15 pm - 6:59 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
19h 44m2 stops Honolulu San Diego
Multiple Airlines Logo
7:57 pm - 2:08 pmORD  Chicago O'Hare Intl-KOA Kona Intl
22h 11m2 stops San Diego Honolulu
$481Multiple Airlines
Wed, Nov 11 - Mon, Nov 16
American Airlines Logo
9:45 pm - 12:59 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
10h 14m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
6:50 am - 3:02 pmORD  Chicago O'Hare Intl-KOA Kona Intl
12h 12m1 stop Phoenix Sky Harbor Intl
$636American Airlines
Thu, Oct 22 - Tue, Nov 10
American Airlines Logo
10:09 pm - 3:00 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
12h 51m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
8:48 pm - 3:02 pmORD  Chicago O'Hare Intl-KOA Kona Intl
22h 14m1 stop Phoenix Sky Harbor Intl
$694American Airlines
Wed, Nov 25 - Sun, Nov 29

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Delta flights from Kailua-Kona to Chicago

Our best Delta deals on Kailua-Kona to Chicago flight tickets
Delta
Oct 27
KOA9:06 pmKona Intl
14h 47m
1 stop
ORD4:53 pmChicago O'Hare Intl
Nov 17
ORD7:35 amChicago O'Hare Intl
11h 25m
1 stop
KOA3:00 pmKona Intl
$470
Delta
Oct 27
KOA9:06 pmKona Intl
11h 24m
1 stop
ORD1:30 pmChicago O'Hare Intl
Nov 17
ORD6:23 amChicago O'Hare Intl
17h 02m
2 stops
KOA7:25 pmKona Intl
$476
Delta
Oct 27
KOA9:06 pmKona Intl
16h 04m
2 stops
ORD6:10 pmChicago O'Hare Intl
Nov 17
ORD6:23 amChicago O'Hare Intl
17h 02m
2 stops
KOA7:25 pmKona Intl
$481

American Airlines flights from Kailua-Kona to Chicago

Our best American Airlines deals on Kailua-Kona to Chicago flight tickets
American Airlines
Oct 22
KOA9:45 pmKona Intl
10h 14m
1 stop
ORD12:59 pmChicago O'Hare Intl
Nov 10
ORD6:50 amChicago O'Hare Intl
12h 12m
1 stop
KOA3:02 pmKona Intl
$636
American Airlines
Oct 1
KOA3:34 pmKona Intl
20h 15m
1 stop
ORD4:49 pmChicago O'Hare Intl
Oct 5
ORD5:00 amChicago O'Hare Intl
14h 03m
1 stop
KOA2:03 pmKona Intl
$766
American Airlines
Oct 1
KOA3:34 pmKona Intl
15h 48m
1 stop
ORD12:22 pmChicago O'Hare Intl
Oct 5
ORD6:00 amChicago O'Hare Intl
14h 17m
2 stops
KOA3:17 pmKona Intl
$812

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 11/5

11:34 am-1:17 pm

1 stop21h 43m

Chicago O'Hare Intl

Sat 11/14

2:15 pm-3:52 pm

1 stop29h 37m

$470

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Tue 10/27

9:06 pm-4:53 pm

1 stop14h 47m

Chicago O'Hare Intl

Tue 11/17

7:35 am-3:00 pm

1 stop11h 25m

$470

Kailua-KonaChicago

KOA Kona Intl - MDW Chicago Midway

KOAMDW

Kona Intl

Wed 11/11

11:40 am-5:55 am

2 stops14h 15m

Chicago Midway

Mon 11/16

5:20 am-2:15 pm

2 stops12h 55m

$470

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Wed 11/11

11:34 am-1:17 pm

1 stop21h 43m

Chicago O'Hare Intl

Mon 11/16

2:15 pm-3:52 pm

1 stop29h 37m

$470

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Thu 11/5

7:15 pm-6:59 pm

2 stops19h 44m

Chicago O'Hare Intl

Sat 11/14

2:15 pm-3:52 pm

1 stop29h 37m

$475

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Wed 11/11

7:15 pm-6:59 pm

2 stops19h 44m

Chicago O'Hare Intl

Mon 11/16

2:15 pm-3:52 pm

1 stop29h 37m

$475

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Tue 10/27

9:06 pm-1:30 pm

1 stop11h 24m

Chicago O'Hare Intl

Tue 11/17

6:23 am-7:25 pm

2 stops17h 02m

$476

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Wed 11/11

7:15 pm-6:59 pm

2 stops19h 44m

Chicago O'Hare Intl

Mon 11/16

7:57 pm-2:08 pm

2 stops22h 11m

$481
Quickest round-trip

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Thu 10/22

9:45 pm-12:59 pm

1 stop10h 14m

Chicago O'Hare Intl

Tue 11/10

6:50 am-3:02 pm

1 stop12h 12m

$636

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Wed 11/25

10:09 pm-3:00 pm

1 stop12h 51m

Chicago O'Hare Intl

Sun 11/29

8:48 pm-3:02 pm

1 stop22h 14m

$694

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 $550. If you’re not able to fly to Chicago in October, then December is your next best option. Flight prices from Kailua-Kona to Chicago during December average around $653.

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 31% 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 September 2026, prices for Kailua-Kona to Chicago flights are approximately 52% more expensive 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

$229

Fastest flight time

13h 49m

Direct flights

Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Kailua-Kona in the past 72 hours is $229. The best round-trip flight deal from Kailua-Kona to Chicago found on momondo in the last 72 hours is $470.
The fastest flight from Kailua-Kona to Chicago takes 13h 49m
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 13h 49m.

  • 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
American AirlinesPriceFrom $422Free CancellationRating
7.1
12,075 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
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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