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Cheap flights from Kailua-Kona to Chicago from $257

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 8/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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
12:38 pm - 6:20 am
KOA
-
ORD
12h 42m
1 stop
Alaska Airlines Logo
7:20 am - 2:48 pm
ORD
-
KOA
12h 28m
1 stop
$514Alaska Airlines
Thu, Sep 24 - Mon, Sep 28
Multiple Airlines Logo
12:38 pm - 6:20 am
KOA
-
ORD
12h 42m
1 stop
Multiple Airlines Logo
7:20 am - 6:17 pm
ORD
-
KOA
15h 57m
2 stops
$520Multiple Airlines
Thu, Sep 24 - Mon, Sep 28
Multiple Airlines Logo
6:00 am - 11:59 pm
KOA
-
ORD
12h 59m
2 stops
Multiple Airlines Logo
7:20 am - 7:32 pm
ORD
-
KOA
17h 12m
2 stops
$525Multiple Airlines
Thu, Sep 24 - Mon, Sep 28
Alaska Airlines Logo
10:36 am - 1:25 pm
KOA
-
ORD
21h 49m
1 stop
Alaska Airlines Logo
2:21 pm - 2:46 pm
ORD
-
KOA
29h 25m
1 stop
$554Alaska Airlines
Wed, Oct 14 - Mon, Oct 19
Multiple Airlines Logo
6:00 am - 11:49 pm
KOA
-
ORD
13h 49m
2 stops
Multiple Airlines Logo
7:25 am - 3:52 pm
ORD
-
KOA
12h 27m
1 stop
$560Multiple Airlines
Tue, Nov 3 - Wed, Nov 4
Multiple Airlines Logo
6:00 am - 11:49 pm
KOA
-
ORD
13h 49m
2 stops
Multiple Airlines Logo
7:00 am - 7:33 pm
ORD
-
KOA
16h 33m
2 stops
$565Multiple Airlines
Tue, Nov 3 - Wed, Nov 4
Multiple Airlines Logo
3:46 pm - 6:53 pm
KOA
-
ORD
22h 07m
2 stops
Multiple Airlines Logo
7:16 pm - 12:40 pm
ORD
-
KOA
22h 24m
2 stops
$577Multiple Airlines
Wed, Oct 14 - Mon, Oct 19
Southwest Logo
8:35 pm - 1:15 pm
KOA
-
MDW
11h 40m
1 stop
Southwest Logo
5:10 am - 2:10 pm
MDW
-
KOA
14h 00m
2 stops
$591Southwest
Wed, Oct 14 - Mon, Oct 19
Southwest Logo
7:05 pm - 1:05 pm
KOA
-
MDW
13h 00m
2 stops
Southwest Logo
5:10 am - 2:10 pm
MDW
-
KOA
14h 00m
2 stops
$642Southwest
Wed, Oct 14 - Mon, Oct 19
United Airlines Logo
7:00 am - 10:59 pm
KOA
-
ORD
10h 59m
1 stop
United Airlines Logo
3:26 pm - 9:45 pm
ORD
-
KOA
11h 19m
1 stop
$684United Airlines
Wed, Jul 15 - Tue, Jul 21

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United Airlines flights from Kailua-Kona to Chicago

Our best United Airlines deals on Kailua-Kona to Chicago flight tickets
United Airlines
Jul 15
KOA7:00 amKona Intl
10h 59m
1 stop
ORD10:59 pmChicago O'Hare Intl
Jul 21
ORD3:26 pmChicago O'Hare Intl
11h 19m
1 stop
KOA9:45 pmKona Intl
$684
United Airlines
Jul 10
KOA12:57 pmKona Intl
11h 49m
1 stop
ORD5:46 amChicago O'Hare Intl
Jul 16
ORD6:00 amChicago O'Hare Intl
10h 42m
1 stop
KOA11:42 amKona Intl
$700
United Airlines
Jun 27
KOA7:00 amKona Intl
10h 59m
1 stop
ORD10:59 pmChicago O'Hare Intl
Jul 1
ORD3:26 pmChicago O'Hare Intl
11h 19m
1 stop
KOA9:45 pmKona Intl
$748

Alaska Airlines flights from Kailua-Kona to Chicago

Our best Alaska Airlines deals on Kailua-Kona to Chicago flight tickets
Alaska Airlines
Sep 24
KOA12:38 pmKona Intl
12h 42m
1 stop
ORD6:20 amChicago O'Hare Intl
Sep 28
ORD7:20 amChicago O'Hare Intl
12h 28m
1 stop
KOA2:48 pmKona Intl
$514
Alaska Airlines
Oct 14
KOA10:36 amKona Intl
21h 49m
1 stop
ORD1:25 pmChicago O'Hare Intl
Oct 19
ORD2:21 pmChicago O'Hare Intl
29h 25m
1 stop
KOA2:46 pmKona Intl
$554
Alaska Airlines
Nov 3
KOA8:05 amKona Intl
11h 52m
1 stop
ORD11:57 pmChicago O'Hare Intl
Nov 4
ORD7:25 amChicago O'Hare Intl
12h 27m
1 stop
KOA3:52 pmKona Intl
$599

momondo Fare Finder

 
Customize your flight search to find flights from Kailua-Kona to Chicago 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 June 16, 2026.
Use the filters below to find and compare flights from Kailua-Kona to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 9/24

12:38 pm-6:20 am

1 stop12h 42m

Chicago O'Hare Intl

Mon 9/28

7:20 am-2:48 pm

1 stop12h 28m

$514

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 9/24

12:38 pm-6:20 am

1 stop12h 42m

Chicago O'Hare Intl

Mon 9/28

7:20 am-6:17 pm

2 stops15h 57m

$520

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 9/24

6:00 am-11:59 pm

2 stops12h 59m

Chicago O'Hare Intl

Mon 9/28

7:20 am-7:32 pm

2 stops17h 12m

$525

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 10/14

10:36 am-1:25 pm

1 stop21h 49m

Chicago O'Hare Intl

Mon 10/19

2:21 pm-2:46 pm

1 stop29h 25m

$554

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 11/3

6:00 am-11:49 pm

2 stops13h 49m

Chicago O'Hare Intl

Wed 11/4

7:25 am-3:52 pm

1 stop12h 27m

$560

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 11/3

6:00 am-11:49 pm

2 stops13h 49m

Chicago O'Hare Intl

Wed 11/4

7:00 am-7:33 pm

2 stops16h 33m

$565

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 10/14

3:46 pm-6:53 pm

2 stops22h 07m

Chicago O'Hare Intl

Mon 10/19

7:16 pm-12:40 pm

2 stops22h 24m

$577

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 10/14

8:35 pm-1:15 pm

1 stop11h 40m

Chicago Midway

Mon 10/19

5:10 am-2:10 pm

2 stops14h 00m

$591

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 10/14

7:05 pm-1:05 pm

2 stops13h 00m

Chicago Midway

Mon 10/19

5:10 am-2:10 pm

2 stops14h 00m

$642
Quickest round-trip

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 7/15

7:00 am-10:59 pm

1 stop10h 59m

Chicago O'Hare Intl

Tue 7/21

3:26 pm-9:45 pm

1 stop11h 19m

$684

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 typical price of a round-trip flight between Kailua-Kona and Chicago?

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Kailua-Kona, with most prices found around $335. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Kailua-Kona to Chicago during February average around $421.

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 21% 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 June 2026, prices for Kailua-Kona to Chicago flights are approximately 18% 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

$778

Fastest flight time

12h 30m

Direct flights

None
The best flight deal from Kailua-Kona to Chicago found on momondo in the last 72 hours is $778
The fastest flight from Kailua-Kona to Chicago takes 12h 30m
There are no direct flights from Kailua-Kona to Chicago. Popular non-direct route for this connection is Kona Intl Airport - Chicago O'Hare Intl Airport.
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 30m.

  • 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
11,666 reviews
Search American Airlines flights
United AirlinesPriceFrom $447Free CancellationRating
7.4
9,842 reviews
Search United 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
Benton Harbor
Portage
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
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

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport