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Cheap flights from Kailua-Kona to Chicago from $207

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 1/14. 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

Enter your travel dates to find the best prices.
Alaska Airlines Logo
2:51 pm - 2:29 pm
KOA
-
ORD
19h 38m1 stop
Alaska Airlines Logo
9:00 am - 6:26 am
ORD
-
KOA
25h 26m2 stops
$399Alaska Airlines
Wed, Jan 14 - Wed, Feb 4
Alaska Airlines Logo
1:43 pm - 2:29 pm
KOA
-
ORD
20h 46m2 stops
Alaska Airlines Logo
9:00 am - 6:26 am
ORD
-
KOA
25h 26m2 stops
$404Alaska Airlines
Wed, Jan 14 - Wed, Feb 4
Alaska Airlines Logo
2:51 pm - 2:29 pm
KOA
-
ORD
19h 38m1 stop
Alaska Airlines Logo
8:20 am - 10:15 pm
ORD
-
KOA
17h 55m2 stops
$409Alaska Airlines
Tue, Feb 10 - Wed, Feb 18
Alaska Airlines Logo
2:51 pm - 2:29 pm
KOA
-
ORD
19h 38m1 stop
Alaska Airlines Logo
8:00 am - 9:30 pm
ORD
-
KOA
17h 30m1 stop
$414Alaska Airlines
Wed, Jan 14 - Wed, Feb 4
Alaska Airlines Logo
2:24 pm - 11:37 pm
KOA
-
ORD
29h 13m1 stop
Alaska Airlines Logo
3:07 pm - 12:53 pm
ORD
-
KOA
25h 46m2 stops
$420Alaska Airlines
Mon, Feb 9 - Mon, Feb 16
Delta Logo
8:45 pm - 1:22 pm
KOA
-
ORD
12h 37m1 stop
Delta Logo
7:30 am - 6:47 pm
ORD
-
KOA
15h 17m1 stop
$434Delta
Mon, Jan 19 - Thu, Jan 22
Delta Logo
10:55 pm - 9:52 pm
KOA
-
ORD
18h 57m2 stops
Delta Logo
7:40 am - 6:30 pm
ORD
-
KOA
14h 50m2 stops
$435Delta
Tue, Feb 10 - Tue, Feb 17
Southwest Logo
9:25 pm - 2:55 pm
KOA
-
MDW
13h 30m2 stops
Southwest Logo
5:35 am - 1:50 pm
MDW
-
KOA
12h 15m1 stop
$843Southwest
Sat, Jan 10 - Sat, Jan 17
Southwest Logo
9:25 pm - 2:55 pm
KOA
-
MDW
13h 30m2 stops
Southwest Logo
8:20 am - 9:20 pm
MDW
-
KOA
17h 00m2 stops
$914Southwest
Sat, Jan 10 - Sat, Jan 17
Southwest Logo
9:25 pm - 1:45 pm
KOA
-
MDW
12h 20m1 stop
Southwest Logo
5:35 am - 1:50 pm
MDW
-
KOA
12h 15m1 stop
$973Southwest
Sat, Jan 10 - Sat, Jan 17

American Airlines flights from Kailua-Kona to Chicago

Our best American Airlines deals on Kailua-Kona to Chicago flight tickets
American Airlines
Dec 31
KOA6:30 pmKona Intl
11h 14m
1 stop
ORD9:44 amChicago O'Hare Intl
Jan 6
ORD7:00 amChicago O'Hare Intl
11h 54m
1 stop
KOA2:54 pmKona Intl
$616
Find similar
American Airlines
Dec 20
KOA6:30 pmKona Intl
13h 14m
1 stop
ORD11:44 amChicago O'Hare Intl
Jan 10
ORD6:40 pmChicago O'Hare Intl
24h 14m
1 stop
KOA2:54 pmKona Intl
$639
Find similar
American Airlines
Dec 20
KOA4:24 pmKona Intl
10h 35m
1 stop
ORD6:59 amChicago O'Hare Intl
Jan 1
ORD6:00 amChicago O'Hare Intl
12h 54m
1 stop
KOA2:54 pmKona Intl
$712
Find similar

Southwest flights from Kailua-Kona to Chicago

Our best Southwest deals on Kailua-Kona to Chicago flight tickets
Southwest
Dec 20
KOA9:15 pmKona Intl
15h 00m
2 stops
ORD4:15 pmChicago O'Hare Intl
Jan 1
ORD7:15 amChicago O'Hare Intl
18h 05m
2 stops
KOA9:20 pmKona Intl
$773
Find similar
Southwest
Dec 20
KOA9:15 pmKona Intl
15h 00m
2 stops
ORD4:15 pmChicago O'Hare Intl
Jan 10
ORD7:15 amChicago O'Hare Intl
14h 55m
2 stops
KOA6:10 pmKona Intl
$783
Find similar
Southwest
Jan 10
KOA9:25 pmKona Intl
13h 30m
2 stops
MDW2:55 pmChicago Midway
Jan 17
MDW5:35 amChicago Midway
12h 15m
1 stop
KOA1:50 pmKona Intl
$843
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 December 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

Wed 1/14

2:51 pm-2:29 pm

1 stop19h 38m

Chicago O'Hare Intl

Wed 2/4

9:00 am-6:26 am

2 stops25h 26m

$399

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 1/14

1:43 pm-2:29 pm

2 stops20h 46m

Chicago O'Hare Intl

Wed 2/4

9:00 am-6:26 am

2 stops25h 26m

$404

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 2/10

2:51 pm-2:29 pm

1 stop19h 38m

Chicago O'Hare Intl

Wed 2/18

8:20 am-10:15 pm

2 stops17h 55m

$409

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 1/14

2:51 pm-2:29 pm

1 stop19h 38m

Chicago O'Hare Intl

Wed 2/4

8:00 am-9:30 pm

1 stop17h 30m

$414

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 2/9

2:24 pm-11:37 pm

1 stop29h 13m

Chicago O'Hare Intl

Mon 2/16

3:07 pm-12:53 pm

2 stops25h 46m

$420

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Mon 1/19

8:45 pm-1:22 pm

1 stop12h 37m

Chicago O'Hare Intl

Thu 1/22

7:30 am-6:47 pm

1 stop15h 17m

$434

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 2/10

10:55 pm-9:52 pm

2 stops18h 57m

Chicago O'Hare Intl

Tue 2/17

7:40 am-6:30 pm

2 stops14h 50m

$435

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sat 1/10

9:25 pm-2:55 pm

2 stops13h 30m

Chicago Midway

Sat 1/17

5:35 am-1:50 pm

1 stop12h 15m

$843

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sat 1/10

9:25 pm-2:55 pm

2 stops13h 30m

Chicago Midway

Sat 1/17

8:20 am-9:20 pm

2 stops17h 00m

$914

Kailua-KonaChicago

KOA - MDW

KOAMDW

Kona Intl

Sat 1/10

9:25 pm-1:45 pm

1 stop12h 20m

Chicago Midway

Sat 1/17

5:35 am-1:50 pm

1 stop12h 15m

$973

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 month to fly to Chicago?

The month of December is, on average, the cheapest month to fly to Chicago from Kailua-Kona, with most prices found around $424. If you’re not able to fly to Chicago in December, then October is your next best option. Flight prices from Kailua-Kona to Chicago during October average around $455.

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 $1,221.

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 $1,188.

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 December 2025, prices for Kailua-Kona to Chicago flights are approximately 7% 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

8h 09m

Direct flights

Sun

Airports in Chicago

1 airport
The fastest flight from Kailua-Kona to Chicago takes 8h 09m
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 8h 09m.

  • 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
9,092 reviews
Search United Airlines flights
American AirlinesPriceFrom $545Free CancellationRating
7.2
11,048 reviews
Search American 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