Which layover airport has the shortest connection time from Chicago to Kailua-Kona?

Seattle (SEA) has the shortest average layover time for this route: 1h 09m.

Which airport is the most popular layover for flights between Chicago and Kailua-Kona?

Los Angeles (LAX) was the most common stop: 29% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport has the shortest travel time from Chicago to Kailua-Kona?

Flights connecting via Las Vegas (LAS) have the shortest average one-way travel time: 10h 50m.

How many flights depart from Chicago to Kailua-Kona on average per week?

As of October 2026, 3 flights take off from Chicago and land in Kailua-Kona each week. The most common flight departure day for this route is Wed, with 33% of weekly flights taking off on this day.

What airlines fly to Kailua-Kona?

American Airlines, United Airlines and Alaska Airlines are the top three most popular airlines that fly to Kailua-Kona from Chicago according to our data. American Airlines is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Kailua-Kona. Keep in mind that there are 4 different airlines that fly to Kailua-Kona on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Chicago to Kona Intl?

Southwest, Alaska Airlines, and American Airlines are the most popular carriers operating from Chicago to Kona Intl

Which layover airport offers the lowest fares from Chicago to Kailua-Kona?

Flights via Las Vegas (LAS) offer the lowest average round-trip price of $601.

When did momondo last update prices for flights from Chicago to Kona Intl Airport?

Prices for flights from Chicago to Kona Intl Airport are refreshed on a daily basis.

How many operators does momondo search for flights from Chicago to Kona Intl Airport?

The number of operators available for flights from Chicago to Kona Intl Airport is 4 as of October 2026.

How old do you have to be to fly from Chicago to Kona Intl Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Kona Intl Airport.

What documentation or ID do you need to fly to Kona Intl Airport?

The travel and health documents you'll need for your trip to Kona Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Kona Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$262 Cheap Flights from Chicago to Kailua-Kona in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Kailua-Kona

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:40 am - 5:51 pmORD Chicago O'Hare Intl-KOA Kona Intl

14h 11m2 stops San Diego Lihue

11:29 pm - 2:21 pmKOA Kona Intl-ORD Chicago O'Hare Intl

10h 52m1 stop Seattle/Tacoma Intl

$553Multiple Airlines

Mon, Jan 11 - Mon, Jan 11

7:40 am - 5:51 pmORD Chicago O'Hare Intl-KOA Kona Intl

14h 11m2 stops San Diego Lihue

10:44 am - 1:15 pmKOA Kona Intl-ORD Chicago O'Hare Intl

22h 31m1 stop San Diego

$573Multiple Airlines

Wed, Jan 27 - Wed, Feb 3

6:23 am - 6:32 pmORD Chicago O'Hare Intl-KOA Kona Intl

16h 09m2 stops Minneapolis St Paul Los Angeles

10:45 pm - 11:20 pmKOA Kona Intl-ORD Chicago O'Hare Intl

20h 35m2 stops Los Angeles Atlanta Hartsfield-Jackson

$614Delta

Wed, Nov 25 - Wed, Nov 25

6:23 am - 7:25 pmORD Chicago O'Hare Intl-KOA Kona Intl

17h 02m2 stops Minneapolis St Paul Seattle/Tacoma Intl

10:45 pm - 11:20 pmKOA Kona Intl-ORD Chicago O'Hare Intl

20h 35m2 stops Los Angeles Atlanta Hartsfield-Jackson

$614Delta

Tue, Nov 24 - Wed, Nov 25

7:40 am - 5:51 pmORD Chicago O'Hare Intl-KOA Kona Intl

14h 11m2 stops San Diego Lihue

8:51 am - 11:59 pmKOA Kona Intl-ORD Chicago O'Hare Intl

11h 08m1 stop Seattle/Tacoma Intl

$616Alaska Airlines

Tue, Jan 19 - Tue, Feb 2

7:20 am - 4:37 pmORD Chicago O'Hare Intl-KOA Kona Intl

13h 17m1 stop Phoenix Sky Harbor Intl

3:07 pm - 6:29 amKOA Kona Intl-ORD Chicago O'Hare Intl

11h 22m1 stop Los Angeles

$636American Airlines

Thu, Jan 21 - Thu, Jan 28

7:20 am - 4:37 pmORD Chicago O'Hare Intl-KOA Kona Intl

13h 17m1 stop Phoenix Sky Harbor Intl

10:48 pm - 2:30 pmKOA Kona Intl-ORD Chicago O'Hare Intl

11h 42m1 stop Phoenix Sky Harbor Intl

$636American Airlines

Thu, Feb 4 - Thu, Feb 11

7:40 am - 4:11 pmORD Chicago O'Hare Intl-KOA Kona Intl

12h 31m1 stop San Diego

11:29 pm - 2:21 pmKOA Kona Intl-ORD Chicago O'Hare Intl

10h 52m1 stop Seattle/Tacoma Intl

$636Alaska Airlines

Tue, Jan 19 - Tue, Feb 2

5:00 am - 12:35 pmORD Chicago O'Hare Intl-KOA Kona Intl

12h 35m2 stops Denver Intl San Francisco

1:10 pm - 5:05 amKOA Kona Intl-ORD Chicago O'Hare Intl

10h 55m1 stop Los Angeles

$850United Airlines

Thu, Apr 1 - Thu, Apr 8

11:00 am - 4:19 pmORD Chicago O'Hare Intl-KOA Kona Intl

9h 19mnonstop

2:23 pm - 5:54 amKOA Kona Intl-ORD Chicago O'Hare Intl

11h 31m1 stop Los Angeles

$864United Airlines

Sat, Jan 2 - Thu, Jan 7

Cheap last minute flights

Enter your travel dates to find the best prices.

7:49 pm - 1:32 pmORD Chicago O'Hare Intl-KOA Kona Intl

22h 43m2 stops San Diego Honolulu

8:00 am - 11:59 pmKOA Kona Intl-ORD Chicago O'Hare Intl

11h 59m1 stop Seattle/Tacoma Intl

$720Multiple Airlines

Sun, Oct 25 - Thu, Nov 12

7:49 pm - 1:32 pmORD Chicago O'Hare Intl-KOA Kona Intl

22h 43m2 stops San Diego Honolulu

7:15 pm - 6:59 pmKOA Kona Intl-ORD Chicago O'Hare Intl

19h 44m2 stops Honolulu San Diego

$725Multiple Airlines

Sun, Oct 25 - Thu, Nov 12

7:20 am - 2:48 pmORD Chicago O'Hare Intl-KOA Kona Intl

12h 28m1 stop San Diego

10:21 pm - 2:53 pmKOA Kona Intl-ORD Chicago O'Hare Intl

11h 32m1 stop Seattle/Tacoma Intl

$729Alaska Airlines

Tue, Oct 27 - Tue, Oct 27

6:35 am - 5:38 pmORD Chicago O'Hare Intl-KOA Kona Intl

16h 03m1 stop Seattle/Tacoma Intl

10:02 pm - 1:38 pmKOA Kona Intl-ORD Chicago O'Hare Intl

10h 36m1 stop Los Angeles

$734Delta

Mon, Oct 26 - Tue, Oct 27

6:35 am - 5:38 pmORD Chicago O'Hare Intl-KOA Kona Intl

16h 03m1 stop Seattle/Tacoma Intl

10:55 pm - 3:45 pmKOA Kona Intl-ORD Chicago O'Hare Intl

12h 50m1 stop Los Angeles

$734Delta

Mon, Oct 26 - Mon, Nov 2

7:20 am - 2:48 pmORD Chicago O'Hare Intl-KOA Kona Intl

12h 28m1 stop San Diego

10:21 pm - 4:50 pmKOA Kona Intl-ORD Chicago O'Hare Intl

13h 29m1 stop Seattle/Tacoma Intl

$734Alaska Airlines

Tue, Oct 27 - Wed, Oct 28

7:20 am - 6:28 pmORD Chicago O'Hare Intl-KOA Kona Intl

16h 08m2 stops San Diego Honolulu

8:45 pm - 6:20 pmKOA Kona Intl-ORD Chicago O'Hare Intl

16h 35m2 stops Honolulu Seattle/Tacoma Intl

$739Multiple Airlines

Tue, Oct 27 - Tue, Oct 27

10:45 pm - 2:03 pmORD Chicago O'Hare Intl-KOA Kona Intl

20h 18m1 stop Phoenix Sky Harbor Intl

10:21 pm - 1:40 pmKOA Kona Intl-ORD Chicago O'Hare Intl

11h 19m1 stop Phoenix Sky Harbor Intl

$772American Airlines

Sun, Oct 25 - Thu, Nov 12

6:00 am - 7:32 pmORD Chicago O'Hare Intl-KOA Kona Intl

18h 32m2 stops Los Angeles San Francisco

2:14 pm - 5:58 amKOA Kona Intl-ORD Chicago O'Hare Intl

11h 44m1 stop Los Angeles

$2,126United Airlines

Tue, Oct 27 - Tue, Nov 3

6:00 am - 7:32 pmORD Chicago O'Hare Intl-KOA Kona Intl

18h 32m2 stops Los Angeles San Francisco

6:00 am - 10:59 pmKOA Kona Intl-ORD Chicago O'Hare Intl

12h 59m2 stops Honolulu Los Angeles

$2,379United Airlines

Tue, Oct 27 - Tue, Nov 3

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Alaska Airlines flights from Chicago to Kailua-Kona

Our best Alaska Airlines deals on Chicago to Kailua-Kona flight tickets

Alaska Airlines

Jan 13

ORD2:13 pmChicago O'Hare Intl

29h 58m

1 stop

KOA4:11 pmKona Intl

Jan 18

KOA10:44 amKona Intl

22h 31m

1 stop

ORD1:15 pmChicago O'Hare Intl

$655

Alaska Airlines

Nov 1

ORD2:15 pmChicago O'Hare Intl

29h 37m

1 stop

KOA3:52 pmKona Intl

Nov 5

KOA11:34 amKona Intl

21h 43m

1 stop

ORD1:17 pmChicago O'Hare Intl

$723

Alaska Airlines

Oct 27

ORD7:20 amChicago O'Hare Intl

12h 28m

1 stop

KOA2:48 pmKona Intl

Oct 27

KOA10:21 pmKona Intl

11h 32m

1 stop

ORD2:53 pmChicago O'Hare Intl

$729

Delta flights from Chicago to Kailua-Kona

Our best Delta deals on Chicago to Kailua-Kona flight tickets

Delta

Dec 7

ORD6:40 amChicago O'Hare Intl

17h 15m

1 stop

KOA7:55 pmKona Intl

Dec 12

KOA8:40 pmKona Intl

18h 29m

2 stops

ORD7:09 pmChicago O'Hare Intl

$620

Delta

Dec 8

ORD5:55 pmChicago O'Hare Intl

28h 41m

2 stops

KOA6:36 pmKona Intl

Dec 11

KOA10:40 pmKona Intl

18h 21m

1 stop

ORD9:01 pmChicago O'Hare Intl

$627

Delta

Mar 30

ORD7:30 amChicago O'Hare Intl

12h 25m

1 stop

KOA2:55 pmKona Intl

Mar 30

KOA9:45 pmKona Intl

10h 46m

1 stop

ORD1:31 pmChicago O'Hare Intl

$631

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Mon 1/11

7:40 am-5:51 pm

2 stops14h 11m

Kona Intl

Mon 1/11

11:29 pm-2:21 pm

1 stop10h 52m

$553

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Wed 1/27

7:40 am-5:51 pm

2 stops14h 11m

Kona Intl

Wed 2/3

10:44 am-1:15 pm

1 stop22h 31m

$573

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Wed 11/25

6:23 am-6:32 pm

2 stops16h 09m

Kona Intl

Wed 11/25

10:45 pm-11:20 pm

2 stops20h 35m

$614

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Tue 11/24

6:23 am-7:25 pm

2 stops17h 02m

Kona Intl

Wed 11/25

10:45 pm-11:20 pm

2 stops20h 35m

$614

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Tue 1/19

7:40 am-5:51 pm

2 stops14h 11m

Kona Intl

Tue 2/2

8:51 am-11:59 pm

1 stop11h 08m

$616

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Thu 1/21

7:20 am-4:37 pm

1 stop13h 17m

Kona Intl

Thu 1/28

3:07 pm-6:29 am

1 stop11h 22m

$636

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Thu 2/4

7:20 am-4:37 pm

1 stop13h 17m

Kona Intl

Thu 2/11

10:48 pm-2:30 pm

1 stop11h 42m

$636

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Tue 1/19

7:40 am-4:11 pm

1 stop12h 31m

Kona Intl

Tue 2/2

11:29 pm-2:21 pm

1 stop10h 52m

$636

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Thu 4/1

5:00 am-12:35 pm

2 stops12h 35m

Kona Intl

Thu 4/8

1:10 pm-5:05 am

1 stop10h 55m

$850

Quickest round-trip

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Sat 1/2

11:00 am-4:19 pm

Nonstop9h 19m

Kona Intl

Thu 1/7

2:23 pm-5:54 am

1 stop11h 31m

$864

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Kailua-Kona

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

Prices

Airlines

Layovers

Other information

What is the typical price of a round-trip flight between Chicago and Kailua-Kona?

Prices are currently typical for flights on this route.

Typical prices usually range from $530 to $1,018.
The lowest price recently found on this route was $553.

What is the cheapest month to fly to Kailua-Kona?

The cheapest month to fly to Kailua-Kona from Chicago is in January. Flight prices, which tend to average around $569, are often lower during this time because this is during the off-season. The month of February is another great option to travel to Kailua-Kona, with average flight prices from Chicago averaging around $608.

What is the cheapest Chicago to Kona Intl flight route?

Fly from Chicago O'Hare Intl to Kona Intl for the best Chicago - Kona Intl flight prices

How far in advance should I book a flight from Chicago to Kailua-Kona?

You are more likely to see cheaper flights to Kailua-Kona from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Kailua-Kona for around $778 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Kailua-Kona from Chicago for as low as $575 on momondo.

What cabin class options are available on Chicago to Kailua-Kona flights?

There are 2 cabin classes available to choose from on Chicago to Kailua-Kona 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 Chicago to Kailua-Kona flights?

You could potentially save up to 45% on your flight if you consider stops on a Chicago to Kailua-Kona flight.

How have Chicago to Kailua-Kona flight prices changed over time?

As of October 2026, prices for Chicago to Kailua-Kona flights are approximately 100% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Kailua-Kona

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Kailua-Kona according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to Kailua-Kona (CHI to KOA) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Kailua-Kona

Best Price Found	$262
Fastest flight time	9h 01m
Direct flights	Sun
Airports in Kailua-Kona	1 airport

The best one-way flight to Kailua-Kona from Chicago in the past 72 hours is $262. The best round-trip flight deal from Chicago to Kailua-Kona found on momondo in the last 72 hours is $553.

The fastest flight from Chicago to Kailua-Kona takes 9h 01m

Direct flights go from Chicago to Kailua-Kona on Sunday. There are no airlines offering direct flights.

There is 1 airport in Kailua-Kona. From Chicago there are direct flights to Kona Intl (KOA).

Search flight deals

Frequently asked questions about flying from Chicago to Kailua-Kona

How far is Chicago to Kona Intl by plane?
The straight-line distance from Chicago to Kona Intl is 4220.2 mi. A reasonable flight in good conditions will take 9h 01m.
When did momondo last update prices for flights from Chicago to Kona Intl Airport?
Prices for flights from Chicago to Kona Intl Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago to Kona Intl Airport?
The number of operators available for flights from Chicago to Kona Intl Airport is 4 as of October 2026.
How old do you have to be to fly from Chicago to Kona Intl Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Kona Intl Airport.
What documentation or ID do you need to fly to Kona Intl Airport?
The travel and health documents you'll need for your trip to Kona Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Kona Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Kailua-Kona?
Based on momondo bookings for flights between Chicago and Kailua-Kona, the leading plane model is Boeing 787-8 Dreamliner, making up 100.00% of the total bookings.
What is the most popular airline from Chicago to Kailua-Kona?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago to Kailua-Kona is American Airlines (41% of total bookings). The next most popular airlines are United Airlines (19%), Delta (17%), and Alaska Airlines (16%).

Best airlines flying from Chicago to Kailua-Kona

Compare and see reviews for airlines that fly from Chicago to Kailua-Kona with momondo

Airline	Rating	Free Cancellation	Price
Alaska Airlines	PriceFrom $403	Free Cancellation	Rating 7.9 13,107 reviews	Search Alaska Airlines flights
Delta	PriceFrom $424	Free Cancellation	Rating 7.8 8,660 reviews	Search Delta flights
American Airlines	PriceFrom $445	Free Cancellation	Rating 7.0 12,183 reviews	Search American Airlines flights
United Airlines	PriceFrom $585	Free Cancellation	Rating 7.3 10,396 reviews	Search United Airlines flights

United Airlines Flights From Chicago to Kailua-Kona
United Airlines is one of the most popular airlines flying from Chicago to Kailua-Kona, operating 3 flights/week on average for this route. A good United Airlines flight deal for Chicago to Kailua-Kona starts from $585 round-trip, up to an average price of $973. Our users have rated United Airlines at 7.3/10.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Kailua-Kona?

Finding the right flight to Kailua-Kona from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Kailua-Kona quick and easy, saving you time and money.

Can I find flights from Chicago to Kailua-Kona with flexible booking policies on momondo?

momondo does allow users to show only those flights to Kailua-Kona from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Kailua-Kona?

momondo provides multiple filters to help you find the best flight to Kailua-Kona from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Kailua-Kona right now. Can momondo alert me if prices change?

Price alerts on flights to Kailua-Kona from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.