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Cheap flights from Kailua-Kona to Chicago from $166

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 1/20. 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

Alaska Airlines Logo
2:20 pm - 7:54 pmKOA-ORD
25h 34m1 stop
Alaska Airlines Logo
8:59 pm - 4:00 pmORD-KOA
23h 01m1 stop
$335Alaska Airlines
Find Deal
Wed, Dec 3 - Sun, Dec 7
Alaska Airlines Logo
2:20 pm - 7:54 pmKOA-ORD
25h 34m1 stop
Alaska Airlines Logo
8:59 pm - 5:52 pmORD-KOA
24h 53m2 stops
$372Alaska Airlines
Find Deal
Wed, Dec 3 - Sun, Dec 7
Alaska Airlines Logo
1:42 pm - 1:59 pmKOA-ORD
20h 17m2 stops
Alaska Airlines Logo
9:00 am - 2:46 pmORD-KOA
33h 46m1 stop
$402Alaska Airlines
Find Deal
Sun, Feb 1 - Sun, Feb 8
Alaska Airlines Logo
9:20 pm - 6:24 amKOA-ORD
28h 04m1 stop
Alaska Airlines Logo
9:20 am - 1:43 pmORD-KOA
33h 23m1 stop
$405Alaska Airlines
Find Deal
Thu, Oct 23 - Thu, Oct 30
Delta Logo
9:55 pm - 1:25 pmKOA-ORD
11h 30m1 stop
Delta Logo
7:30 am - 7:50 pmORD-KOA
16h 20m1 stop
$426Delta
Find Deal
Mon, Feb 2 - Mon, Feb 9
Delta Logo
8:45 pm - 1:25 pmKOA-ORD
12h 40m1 stop
Delta Logo
7:30 am - 7:50 pmORD-KOA
16h 20m1 stop
$447Delta
Find Deal
Thu, Jan 29 - Thu, Feb 5
American Airlines Logo
6:25 pm - 9:52 amKOA-ORD
11h 27m1 stop
American Airlines Logo
7:00 am - 4:47 pmORD-KOA
13h 47m1 stop
$481American Airlines
Find Deal
Wed, Nov 26 - Sun, Nov 30
United Airlines Logo
8:30 pm - 11:25 amKOA-ORD
10h 55m1 stop
United Airlines Logo
1:04 pm - 9:10 pmORD-KOA
12h 06m1 stop
$535United Airlines
Find Deal
Sat, Dec 20 - Fri, Jan 2
Southwest Logo
7:00 pm - 12:30 pmKOA-MDW
13h 30m2 stops
Southwest Logo
6:10 am - 1:15 pmMDW-KOA
12h 05m1 stop
$587Southwest
Find Deal
Wed, Jan 14 - Wed, May 6
Southwest Logo
7:00 pm - 12:30 pmKOA-MDW
13h 30m2 stops
Southwest Logo
10:00 am - 6:05 pmMDW-KOA
13h 05m2 stops
$593Southwest
Find Deal
Wed, Jan 14 - Wed, May 6

Alaska Airlines flights from Kailua-Kona to Chicago

Our best Alaska Airlines deals on Kailua-Kona to Chicago flight tickets
Alaska Airlines
Dec 3
KOA2:20 pmKona Intl
25h 34m
1 stop
ORD7:54 pmChicago O'Hare Intl
Dec 7
ORD8:59 pmChicago O'Hare Intl
23h 01m
1 stop
KOA4:00 pmKona Intl
$335
Find similar
Alaska Airlines
Dec 3
KOA2:20 pmKona Intl
25h 34m
1 stop
ORD7:54 pmChicago O'Hare Intl
Dec 7
ORD8:59 pmChicago O'Hare Intl
24h 53m
2 stops
KOA5:52 pmKona Intl
$372
Find similar
Alaska Airlines
Feb 1
KOA1:42 pmKona Intl
20h 17m
2 stops
ORD1:59 pmChicago O'Hare Intl
Feb 8
ORD9:00 amChicago O'Hare Intl
33h 46m
1 stop
KOA2:46 pmKona Intl
$402
Find similar

Delta flights from Kailua-Kona to Chicago

Our best Delta deals on Kailua-Kona to Chicago flight tickets
Delta
Feb 2
KOA9:55 pmKona Intl
11h 30m
1 stop
ORD1:25 pmChicago O'Hare Intl
Feb 9
ORD7:30 amChicago O'Hare Intl
16h 20m
1 stop
KOA7:50 pmKona Intl
$426
Find similar
Delta
Jan 29
KOA8:45 pmKona Intl
12h 40m
1 stop
ORD1:25 pmChicago O'Hare Intl
Feb 5
ORD7:30 amChicago O'Hare Intl
16h 20m
1 stop
KOA7:50 pmKona Intl
$447
Find similar
Delta
Oct 23
KOA9:30 pmKona Intl
11h 00m
1 stop
ORD1:30 pmChicago O'Hare Intl
Oct 30
ORD7:50 amChicago O'Hare Intl
14h 40m
2 stops
KOA5:30 pmKona Intl
$452
Find similar

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 September 26, 2025.
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

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 12/3

2:20 pm-7:54 pm

1 stop25h 34m

Chicago O'Hare Intl

Sun 12/7

8:59 pm-4:00 pm

1 stop23h 01m

$335

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 12/3

2:20 pm-7:54 pm

1 stop25h 34m

Chicago O'Hare Intl

Sun 12/7

8:59 pm-5:52 pm

2 stops24h 53m

$372

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sun 2/1

1:42 pm-1:59 pm

2 stops20h 17m

Chicago O'Hare Intl

Sun 2/8

9:00 am-2:46 pm

1 stop33h 46m

$402

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 10/23

9:20 pm-6:24 am

1 stop28h 04m

Chicago O'Hare Intl

Thu 10/30

9:20 am-1:43 pm

1 stop33h 23m

$405

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 2/2

9:55 pm-1:25 pm

1 stop11h 30m

Chicago O'Hare Intl

Mon 2/9

7:30 am-7:50 pm

1 stop16h 20m

$426

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 1/29

8:45 pm-1:25 pm

1 stop12h 40m

Chicago O'Hare Intl

Thu 2/5

7:30 am-7:50 pm

1 stop16h 20m

$447

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 11/26

6:25 pm-9:52 am

1 stop11h 27m

Chicago O'Hare Intl

Sun 11/30

7:00 am-4:47 pm

1 stop13h 47m

$481

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 12/20

8:30 pm-11:25 am

1 stop10h 55m

Chicago O'Hare Intl

Fri 1/2

1:04 pm-9:10 pm

1 stop12h 06m

$535

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 1/14

7:00 pm-12:30 pm

2 stops13h 30m

Chicago Midway

Wed 5/6

6:10 am-1:15 pm

1 stop12h 05m

$587

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 1/14

7:00 pm-12:30 pm

2 stops13h 30m

Chicago Midway

Wed 5/6

10:00 am-6:05 pm

2 stops13h 05m

$593

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 day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Monday when prices can be found for as low as $467. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Kailua-Kona to Chicago for around $1,188.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Kailua-Kona to Chicago during this time can be as low as $456. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $1,135.

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 Kona Intl to Chicago flights?

There are 3 cabin classes available to choose from on Kona Intl to Chicago 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 flight prices changed over time?

As of September 2025, prices for Kailua-Kona to Chicago flights are approximately 10% 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

Fastest flight time

7h 55m

Direct flights

Sun

Airports in Chicago

1 airport
The fastest flight from Kailua-Kona to Chicago takes 7h 55m
Direct flights go from Kailua-Kona to Chicago on Sunday. There are no airlines offering direct flights.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

  • 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 10h 25m.

  • 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
United AirlinesPriceFrom $429Free CancellationRating
7.4
8,928 reviews
Search United Airlines flights
American AirlinesPriceFrom $447Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $458Free 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
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