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Cheap flights from Kailua-Kona to Chicago from $211

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 2/27. 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
0 bags

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Find the cheapest flights from Kailua-Kona to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
10:11 pm - 12:31 pm
KOA
-
ORD
10h 20m
1 stop
American Airlines Logo
9:25 am - 6:59 pm
ORD
-
KOA
13h 34m
1 stop
$422American Airlines
Wed, Feb 18 - Sun, Feb 22
Multiple Airlines Logo
6:56 pm - 6:26 pm
KOA
-
ORD
18h 30m
2 stops
Multiple Airlines Logo
8:20 am - 2:59 pm
ORD
-
KOA
11h 39m
1 stop
$431Multiple Airlines
Tue, Apr 7 - Tue, Apr 14
American Airlines Logo
10:11 pm - 12:31 pm
KOA
-
ORD
10h 20m
1 stop
American Airlines Logo
11:31 am - 6:59 pm
ORD
-
KOA
11h 28m
1 stop
$445American Airlines
Tue, Feb 17 - Thu, Feb 26
Multiple Airlines Logo
6:56 pm - 6:26 pm
KOA
-
ORD
18h 30m
2 stops
Multiple Airlines Logo
8:20 am - 8:26 pm
ORD
-
KOA
17h 06m
2 stops
$456Multiple Airlines
Tue, Apr 7 - Tue, Apr 14
Alaska Airlines Logo
10:07 pm - 6:39 am
KOA
-
ORD
27h 32m
1 stop
Alaska Airlines Logo
8:20 am - 2:59 pm
ORD
-
KOA
11h 39m
1 stop
$483Alaska Airlines
Tue, Apr 7 - Tue, Apr 14
Alaska Airlines Logo
1:10 pm - 2:58 pm
KOA
-
ORD
21h 48m
1 stop
Alaska Airlines Logo
3:07 pm - 3:53 pm
ORD
-
KOA
28h 46m
1 stop
$497Alaska Airlines
Wed, Feb 18 - Sun, Feb 22
Delta Logo
10:55 pm - 6:59 pm
KOA
-
ORD
16h 04m
2 stops
Delta Logo
6:15 am - 7:39 pm
ORD
-
KOA
17h 24m
2 stops
$515Delta
Wed, Feb 18 - Sun, Feb 22
Southwest Logo
9:25 pm - 3:00 pm
KOA
-
MDW
13h 35m
1 stop
Southwest Logo
7:55 am - 6:10 pm
MDW
-
KOA
14h 15m
2 stops
$568Southwest
Thu, Feb 12 - Tue, Feb 17
Southwest Logo
9:25 pm - 3:05 pm
KOA
-
MDW
13h 40m
2 stops
Southwest Logo
7:55 am - 9:20 pm
MDW
-
KOA
17h 25m
2 stops
$573Southwest
Thu, Feb 12 - Tue, Feb 17
Delta Logo
10:55 pm - 5:37 pm
KOA
-
MDW
14h 42m
2 stops
Delta Logo
9:34 am - 7:39 pm
MDW
-
KOA
14h 05m
2 stops
$615Delta
Wed, Feb 18 - Sun, Feb 22

Alaska Airlines flights from Kailua-Kona to Chicago

Our best Alaska Airlines deals on Kailua-Kona to Chicago flight tickets
Alaska Airlines
Feb 28
KOA12:53 pmKona Intl
31h 06m
1 stop
ORD11:59 pmChicago O'Hare Intl
Mar 7
ORD3:07 pmChicago O'Hare Intl
27h 46m
1 stop
KOA2:53 pmKona Intl
$482
Alaska Airlines
Apr 7
KOA10:07 pmKona Intl
27h 32m
1 stop
ORD6:39 amChicago O'Hare Intl
Apr 14
ORD8:20 amChicago O'Hare Intl
11h 39m
1 stop
KOA2:59 pmKona Intl
$483
Alaska Airlines
Feb 18
KOA1:10 pmKona Intl
21h 48m
1 stop
ORD2:58 pmChicago O'Hare Intl
Feb 22
ORD3:07 pmChicago O'Hare Intl
28h 46m
1 stop
KOA3:53 pmKona Intl
$497

Delta flights from Kailua-Kona to Chicago

Our best Delta deals on Kailua-Kona to Chicago flight tickets
Delta
Feb 18
KOA10:55 pmKona Intl
16h 04m
2 stops
ORD6:59 pmChicago O'Hare Intl
Feb 22
ORD6:15 amChicago O'Hare Intl
17h 24m
2 stops
KOA7:39 pmKona Intl
$515
Delta
Feb 16
KOA9:55 pmKona Intl
11h 27m
1 stop
ORD1:22 pmChicago O'Hare Intl
Feb 26
ORD7:15 amChicago O'Hare Intl
15h 15m
2 stops
KOA6:30 pmKona Intl
$532
Delta
Feb 16
KOA8:55 pmKona Intl
15h 46m
2 stops
ORD4:41 pmChicago O'Hare Intl
Feb 26
ORD7:15 amChicago O'Hare Intl
15h 15m
2 stops
KOA6:30 pmKona Intl
$537

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 January 26, 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

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 2/18

10:11 pm-12:31 pm

1 stop10h 20m

Chicago O'Hare Intl

Sun 2/22

9:25 am-6:59 pm

1 stop13h 34m

$422

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 4/7

6:56 pm-6:26 pm

2 stops18h 30m

Chicago O'Hare Intl

Tue 4/14

8:20 am-2:59 pm

1 stop11h 39m

$431

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 2/17

10:11 pm-12:31 pm

1 stop10h 20m

Chicago O'Hare Intl

Thu 2/26

11:31 am-6:59 pm

1 stop11h 28m

$445

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 4/7

6:56 pm-6:26 pm

2 stops18h 30m

Chicago O'Hare Intl

Tue 4/14

8:20 am-8:26 pm

2 stops17h 06m

$456

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 4/7

10:07 pm-6:39 am

1 stop27h 32m

Chicago O'Hare Intl

Tue 4/14

8:20 am-2:59 pm

1 stop11h 39m

$483

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 2/18

1:10 pm-2:58 pm

1 stop21h 48m

Chicago O'Hare Intl

Sun 2/22

3:07 pm-3:53 pm

1 stop28h 46m

$497

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 2/18

10:55 pm-6:59 pm

2 stops16h 04m

Chicago O'Hare Intl

Sun 2/22

6:15 am-7:39 pm

2 stops17h 24m

$515

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 2/12

9:25 pm-3:00 pm

1 stop13h 35m

Chicago Midway

Tue 2/17

7:55 am-6:10 pm

2 stops14h 15m

$568

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Thu 2/12

9:25 pm-3:05 pm

2 stops13h 40m

Chicago Midway

Tue 2/17

7:55 am-9:20 pm

2 stops17h 25m

$573

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 2/18

10:55 pm-5:37 pm

2 stops14h 42m

Chicago Midway

Sun 2/22

9:34 am-7:39 pm

2 stops14h 05m

$615

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 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 2 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 January 2026, prices for Kailua-Kona to Chicago flights are approximately 20% 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

$322

Fastest flight time

12h 30m

Direct flights

Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Kailua-Kona in the past 72 hours is $322. The best round-trip 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
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

  • 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
United AirlinesPriceFrom $447Free CancellationRating
7.4
9,199 reviews
Search United Airlines flights
American AirlinesPriceFrom $468Free CancellationRating
7.2
11,189 reviews
Search American Airlines flights

  • United Airlines Flights From Kailua-Kona to Chicago

    United Airlines flies from Kailua-Kona to Chicago around 1 time per week, with 9,199 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Kailua-Kona to Chicago in the last 72 hours was $447 (round-trip), much lower than the average airfare cost of $792 for United Airlines flights on this route.

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
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