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Cheap flights from Kailua-Kona to Chicago from $200

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 9/26. 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 (KOA-CHI)

Cheap round-trip flights

Alaska Airlines Logo
8:00 am - 12:03 amKOA-ORD
11h 03m1 stop
Alaska Airlines Logo
6:20 am - 4:00 pmORD-KOA
14h 40m1 stop
$409Alaska Airlines
Find Deal
Thu, Sep 4 - Mon, Sep 8
Alaska Airlines Logo
8:00 am - 11:59 pmKOA-ORD
11h 59m1 stop
Alaska Airlines Logo
9:00 am - 7:24 pmORD-KOA
14h 24m2 stops
$414Alaska Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
Alaska Airlines Logo
8:00 am - 11:59 pmKOA-ORD
11h 59m1 stop
Alaska Airlines Logo
2:00 pm - 10:35 pmORD-KOA
12h 35m1 stop
$416Alaska Airlines
Find Deal
Thu, Dec 4 - Tue, Dec 9
Alaska Airlines Logo
9:00 pm - 1:59 pmKOA-ORD
12h 59m2 stops
Alaska Airlines Logo
7:00 am - 4:26 pmORD-KOA
13h 26m2 stops
$420Alaska Airlines
Find Deal
Thu, Dec 4 - Tue, Dec 9
Delta Logo
8:45 pm - 1:28 pmKOA-ORD
12h 43m1 stop
Delta Logo
7:30 am - 7:10 pmORD-KOA
15h 40m1 stop
$423Delta
Find Deal
Wed, Dec 3 - Tue, Dec 9
Hawaiian Airlines Logo
8:00 am - 12:03 amKOA-ORD
11h 03m1 stop
Hawaiian Airlines Logo
10:00 am - 4:44 pmORD-KOA
11h 44m1 stop
$458Hawaiian Airlines
Find Deal
Wed, Sep 24 - Sat, Sep 27
Delta Logo
8:45 pm - 1:28 pmKOA-ORD
12h 43m1 stop
Delta Logo
7:30 am - 7:10 pmORD-KOA
15h 40m1 stop
$465Delta
Find Deal
Sat, Dec 6 - Mon, Dec 8
American Airlines Logo
4:42 pm - 4:00 pmKOA-ORD
19h 18m1 stop
American Airlines Logo
7:00 am - 2:50 pmORD-KOA
11h 50m1 stop
$467American Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
Southwest Logo
9:15 pm - 11:35 amKOA-MDW
10h 20m1 stop
Southwest Logo
5:15 am - 1:40 pmMDW-KOA
12h 25m1 stop
$508Southwest
Find Deal
Wed, Dec 3 - Wed, Dec 10
Southwest Logo
9:15 pm - 1:40 pmKOA-MDW
12h 25m1 stop
Southwest Logo
5:15 am - 6:10 pmMDW-KOA
16h 55m2 stops
$646Southwest
Find Deal
Wed, Dec 3 - Wed, Dec 10

Alaska Airlines flights from Kailua-Kona to Chicago

Our best Alaska Airlines deals on Kailua-Kona to Chicago flight tickets
Alaska Airlines
Sep 4
KOA8:00 amKona Intl
11h 03m
1 stop
ORD12:03 amChicago O'Hare Intl
Sep 8
ORD6:20 amChicago O'Hare Intl
14h 40m
1 stop
KOA4:00 pmKona Intl
$409
Find similar
Alaska Airlines
Dec 4
KOA8:00 amKona Intl
11h 59m
1 stop
ORD11:59 pmChicago O'Hare Intl
Dec 8
ORD9:00 amChicago O'Hare Intl
14h 24m
2 stops
KOA7:24 pmKona Intl
$414
Find similar
Alaska Airlines
Dec 4
KOA8:00 amKona Intl
11h 59m
1 stop
ORD11:59 pmChicago O'Hare Intl
Dec 9
ORD2:00 pmChicago O'Hare Intl
12h 35m
1 stop
KOA10:35 pmKona Intl
$416
Find similar

Delta flights from Kailua-Kona to Chicago

Our best Delta deals on Kailua-Kona to Chicago flight tickets
Delta
Dec 3
KOA8:45 pmKona Intl
12h 43m
1 stop
ORD1:28 pmChicago O'Hare Intl
Dec 9
ORD7:30 amChicago O'Hare Intl
15h 40m
1 stop
KOA7:10 pmKona Intl
$423
Find similar
Delta
Dec 6
KOA8:45 pmKona Intl
12h 43m
1 stop
ORD1:28 pmChicago O'Hare Intl
Dec 8
ORD7:30 amChicago O'Hare Intl
15h 40m
1 stop
KOA7:10 pmKona Intl
$465
Find similar
Delta
Sep 24
KOA9:30 pmKona Intl
10h 50m
1 stop
ORD1:20 pmChicago O'Hare Intl
Sep 27
ORD5:15 pmChicago O'Hare Intl
29h 20m
2 stops
KOA5:35 pmKona Intl
$487
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 August 10, 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

Thu 9/4

8:00 am-12:03 am

1 stop11h 03m

Chicago O'Hare Intl

Mon 9/8

6:20 am-4:00 pm

1 stop14h 40m

$409

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 12/4

8:00 am-11:59 pm

1 stop11h 59m

Chicago O'Hare Intl

Mon 12/8

9:00 am-7:24 pm

2 stops14h 24m

$414

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 12/4

8:00 am-11:59 pm

1 stop11h 59m

Chicago O'Hare Intl

Tue 12/9

2:00 pm-10:35 pm

1 stop12h 35m

$416

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 12/4

9:00 pm-1:59 pm

2 stops12h 59m

Chicago O'Hare Intl

Tue 12/9

7:00 am-4:26 pm

2 stops13h 26m

$420

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 12/3

8:45 pm-1:28 pm

1 stop12h 43m

Chicago O'Hare Intl

Tue 12/9

7:30 am-7:10 pm

1 stop15h 40m

$423

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 9/24

8:00 am-12:03 am

1 stop11h 03m

Chicago O'Hare Intl

Sat 9/27

10:00 am-4:44 pm

1 stop11h 44m

$458

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Sat 12/6

8:45 pm-1:28 pm

1 stop12h 43m

Chicago O'Hare Intl

Mon 12/8

7:30 am-7:10 pm

1 stop15h 40m

$465

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 12/3

4:42 pm-4:00 pm

1 stop19h 18m

Chicago O'Hare Intl

Wed 12/10

7:00 am-2:50 pm

1 stop11h 50m

$467

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 12/3

9:15 pm-11:35 am

1 stop10h 20m

Chicago Midway

Wed 12/10

5:15 am-1:40 pm

1 stop12h 25m

$508

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Wed 12/3

9:15 pm-1:40 pm

1 stop12h 25m

Chicago Midway

Wed 12/10

5:15 am-6:10 pm

2 stops16h 55m

$646

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 $1,135.

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 $1,066.

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?

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

$200

Fastest flight time

10h 14m

Direct flights

None

Airports in Chicago

2 airports
The best one-way flight to Chicago from Kailua-Kona in the past 72 hours is $200. The best round-trip flight deal from Kailua-Kona to Chicago found on momondo in the last 72 hours is $409.
The fastest flight from Kailua-Kona to Chicago takes 10h 14m
There are no direct flights from Kailua-Kona to Chicago. Popular non-direct routes for this connection are Kona Intl Airport - Chicago O'Hare Intl Airport and Kona Intl Airport - Chicago Midway Airport.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
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  • 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 20m.

  • 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 $399Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $429Free CancellationRating
7.4
8,920 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $507Free 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
Lansing
Portage
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