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Cheap flights from Kailua-Kona to Chicago from $292

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 10/9. 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
3:51 pm - 7:21 pm-
22h 30m
Alaska Airlines Logo
7:20 am - 9:32 am-
31h 12m
$573Alaska Airlines
Tue, Sep 15 - Tue, Sep 22
Delta Logo
9:06 pm - 11:50 pm-
21h 44m
Delta Logo
6:59 pm - 7:26 pm-
29h 27m
$578Delta
Wed, Oct 14 - Tue, Oct 20
Delta Logo
9:06 pm - 11:50 pm-
21h 44m
Delta Logo
7:16 am - 7:26 pm-
17h 10m
$578Delta
Wed, Oct 14 - Wed, Oct 21
Delta Logo
9:06 pm - 1:29 pm-
11h 23m
Delta Logo
2:45 pm - 7:26 pm-
33h 41m
$578Delta
Wed, Oct 14 - Wed, Oct 21
American Airlines Logo
9:45 pm - 4:09 pm-
13h 24m
American Airlines Logo
6:48 am - 2:03 pm-
12h 15m
$584American Airlines
Thu, Oct 15 - Wed, Oct 21
American Airlines Logo
9:45 pm - 4:09 pm-
13h 24m
American Airlines Logo
5:00 am - 2:03 pm-
14h 03m
$584American Airlines
Thu, Oct 15 - Tue, Oct 20
American Airlines Logo
9:45 pm - 4:05 pm-
13h 20m
American Airlines Logo
7:09 am - 4:00 pm-
13h 51m
$590American Airlines
Wed, Sep 9 - Sun, Sep 13
United Airlines Logo
12:04 pm - 7:13 am-
14h 09m
United Airlines Logo
9:57 pm - 10:49 am-
17h 52m
$772United Airlines
Tue, Oct 27 - Wed, Oct 28
United Airlines Logo
10:50 pm - 2:50 pm-
11h 00m
United Airlines Logo
10:55 am - 7:35 pm-
13h 40m
$970United Airlines
Sun, Aug 16 - Thu, Aug 20
United Airlines Logo
10:50 pm - 7:00 pm-
15h 10m
United Airlines Logo
5:00 am - 12:48 pm-
12h 48m
$975United Airlines
Sun, Aug 16 - Thu, Aug 20

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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
Sep 9
KOA9:45 pmKona Intl
13h 20m
1 stop
ORD4:05 pmChicago O'Hare Intl
Sep 13
ORD7:09 amChicago O'Hare Intl
13h 51m
2 stops
KOA4:00 pmKona Intl
$590
American Airlines
Sep 2
KOA9:45 pmKona Intl
13h 20m
1 stop
ORD4:05 pmChicago O'Hare Intl
Sep 8
ORD8:20 amChicago O'Hare Intl
12h 55m
2 stops
KOA4:15 pmKona Intl
$600
American Airlines
Sep 9
KOA9:45 pmKona Intl
13h 15m
2 stops
ORD4:00 pmChicago O'Hare Intl
Sep 13
ORD6:00 amChicago O'Hare Intl
15h 00m
2 stops
KOA4:00 pmKona Intl
$640

Delta flights from Kailua-Kona to Chicago

Our best Delta deals on Kailua-Kona to Chicago flight tickets
Delta
Oct 14
KOA9:06 pmKona Intl
21h 44m
2 stops
ORD11:50 pmChicago O'Hare Intl
Oct 20
ORD6:59 pmChicago O'Hare Intl
29h 27m
1 stop
KOA7:26 pmKona Intl
$578
Delta
Oct 14
KOA9:06 pmKona Intl
35h 32m
2 stops
ORD1:38 pmChicago O'Hare Intl
Oct 20
ORD7:15 pmChicago O'Hare Intl
29h 11m
2 stops
KOA7:26 pmKona Intl
$583
Delta
Sep 8
KOA8:55 pmKona Intl
11h 34m
1 stop
ORD1:29 pmChicago O'Hare Intl
Sep 13
ORD7:00 amChicago O'Hare Intl
15h 31m
1 stop
KOA5:31 pmKona Intl
$639

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 August 5, 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

Tue 9/15

3:51 pm-7:21 pm

2 stops22h 30m

Chicago O'Hare Intl

Tue 9/22

7:20 am-9:32 am

2 stops31h 12m

$573

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 10/14

9:06 pm-11:50 pm

2 stops21h 44m

Chicago O'Hare Intl

Tue 10/20

6:59 pm-7:26 pm

1 stop29h 27m

$578

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 10/14

9:06 pm-11:50 pm

2 stops21h 44m

Chicago O'Hare Intl

Wed 10/21

7:16 am-7:26 pm

1 stop17h 10m

$578

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 10/14

9:06 pm-1:29 pm

1 stop11h 23m

Chicago O'Hare Intl

Wed 10/21

2:45 pm-7:26 pm

1 stop33h 41m

$578

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 10/15

9:45 pm-4:09 pm

1 stop13h 24m

Chicago O'Hare Intl

Wed 10/21

6:48 am-2:03 pm

1 stop12h 15m

$584

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 10/15

9:45 pm-4:09 pm

1 stop13h 24m

Chicago O'Hare Intl

Tue 10/20

5:00 am-2:03 pm

1 stop14h 03m

$584

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 9/9

9:45 pm-4:05 pm

1 stop13h 20m

Chicago O'Hare Intl

Sun 9/13

7:09 am-4:00 pm

2 stops13h 51m

$590

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 10/27

12:04 pm-7:13 am

1 stop14h 09m

Chicago O'Hare Intl

Wed 10/28

9:57 pm-10:49 am

1 stop17h 52m

$772
Quickest round-trip

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sun 8/16

10:50 pm-2:50 pm

1 stop11h 00m

Chicago O'Hare Intl

Thu 8/20

10:55 am-7:35 pm

2 stops13h 40m

$970

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sun 8/16

10:50 pm-7:00 pm

2 stops15h 10m

Chicago O'Hare Intl

Thu 8/20

5:00 am-12:48 pm

2 stops12h 48m

$975

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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 February is, on average, the cheapest month to fly to Chicago from Kailua-Kona, with most prices found around $422. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from Kailua-Kona to Chicago during September average around $458.

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 47% 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 August 2026, prices for Kailua-Kona to Chicago flights are approximately 102% 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

Fastest flight time

10h 30m

Direct flights

Sun

Airports in Chicago

3 airports
The fastest flight from Kailua-Kona to Chicago takes 10h 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

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 10h 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?

  • What is the most popular airline 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
11,848 reviews
Search American Airlines flights
United AirlinesPriceFrom $447Free CancellationRating
7.4
10,058 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
Portage
Benton Harbor
Lansing
Saint Joseph
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

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