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 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.

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.

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

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

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 44% 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.

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

Los Angeles (LAX) was the most common stop: 27% of momondo users choosing 1-stop flights on this route connected there.

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 November 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.

$289 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.

8:00 am - 5:53 pmORD Chicago O'Hare Intl-KOA Kona Intl

13h 53m1 stop Seattle/Tacoma Intl

5:54 pm - 1:13 pmKOA Kona Intl-ORD Chicago O'Hare Intl

15h 19m2 stops Honolulu Portland

$566Multiple Airlines

Tue, Jan 26 - Tue, Feb 2

8:00 am - 5:53 pmORD Chicago O'Hare Intl-KOA Kona Intl

13h 53m1 stop Seattle/Tacoma Intl

6:00 am - 11:59 pmKOA Kona Intl-ORD Chicago O'Hare Intl

13h 59m2 stops Honolulu San Diego

$575Multiple Airlines

Mon, Feb 1 - Thu, Feb 11

8:00 am - 5:53 pmORD Chicago O'Hare Intl-KOA Kona Intl

13h 53m1 stop Seattle/Tacoma Intl

8:40 am - 11:59 pmKOA Kona Intl-ORD Chicago O'Hare Intl

11h 19m1 stop Seattle/Tacoma Intl

$576Alaska Airlines

Tue, Jan 12 - Tue, Jan 26

8:00 am - 5:53 pmORD Chicago O'Hare Intl-KOA Kona Intl

13h 53m1 stop Seattle/Tacoma Intl

8:40 am - 11:59 pmKOA Kona Intl-ORD Chicago O'Hare Intl

11h 19m1 stop Seattle/Tacoma Intl

$576Alaska Airlines

Tue, Jan 26 - Tue, Feb 2

7:15 am - 2:57 pmORD Chicago O'Hare Intl-KOA Kona Intl

11h 42m1 stop Salt Lake City

10:45 pm - 1:53 pmKOA Kona Intl-ORD Chicago O'Hare Intl

11h 08m1 stop Los Angeles

$578Delta

Mon, Jan 18 - Fri, Jan 22

7:15 am - 2:57 pmORD Chicago O'Hare Intl-KOA Kona Intl

11h 42m1 stop Salt Lake City

10:45 pm - 1:53 pmKOA Kona Intl-ORD Chicago O'Hare Intl

11h 08m1 stop Los Angeles

$578Delta

Mon, Jan 18 - Thu, Jan 21

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

13h 17m1 stop Phoenix Sky Harbor Intl

9:59 pm - 2:36 pmKOA Kona Intl-ORD Chicago O'Hare Intl

12h 37m1 stop Phoenix Sky Harbor Intl

$646American Airlines

Tue, Jan 26 - Tue, Feb 2

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

13h 17m1 stop Phoenix Sky Harbor Intl

10:48 pm - 1:19 pmKOA Kona Intl-ORD Chicago O'Hare Intl

10h 31m1 stop Phoenix Sky Harbor Intl

$646American Airlines

Wed, Feb 10 - Tue, Feb 16

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

9h 19mnonstop

3:13 pm - 5:36 amKOA Kona Intl-ORD Chicago O'Hare Intl

10h 23m1 stop San Francisco

$870United Airlines

Sat, Jan 9 - Mon, Jan 18

10:25 am - 8:32 pmORD Chicago O'Hare Intl-KOA Kona Intl

14h 07m1 stop San Francisco

5:50 pm - 5:54 amKOA Kona Intl-ORD Chicago O'Hare Intl

8h 04mnonstop

$874United Airlines

Wed, Dec 16 - Sat, Dec 26

Cheap last minute flights

Enter your travel dates to find the best prices.

6:40 am - 7:25 pmORD Chicago O'Hare Intl-KOA Kona Intl

16h 45m1 stop Seattle/Tacoma Intl

10:45 pm - 1:37 pmKOA Kona Intl-ORD Chicago O'Hare Intl

10h 52m1 stop Los Angeles

$724Delta

Thu, Nov 12 - Tue, Nov 17

7:30 am - 7:25 pmORD Chicago O'Hare Intl-KOA Kona Intl

15h 55m2 stops Salt Lake City Seattle/Tacoma Intl

10:45 pm - 1:37 pmKOA Kona Intl-ORD Chicago O'Hare Intl

10h 52m1 stop Los Angeles

$730Delta

Thu, Nov 12 - Tue, Nov 17

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

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

9:45 pm - 6:05 pmKOA Kona Intl-ORD Chicago O'Hare Intl

16h 20m2 stops Seattle/Tacoma Intl Salt Lake City

$735Delta

Thu, Nov 12 - Tue, Nov 17

6:40 am - 7:25 pmORD Chicago O'Hare Intl-KOA Kona Intl

16h 45m1 stop Seattle/Tacoma Intl

9:45 pm - 1:37 pmKOA Kona Intl-ORD Chicago O'Hare Intl

11h 52m1 stop Seattle/Tacoma Intl

$780Delta

Thu, Nov 12 - Sun, Nov 22

6:40 am - 7:25 pmORD Chicago O'Hare Intl-KOA Kona Intl

16h 45m1 stop Seattle/Tacoma Intl

10:45 pm - 6:05 pmKOA Kona Intl-ORD Chicago O'Hare Intl

15h 20m2 stops Los Angeles Salt Lake City

$786Delta

Thu, Nov 12 - Sun, Nov 22

7:20 am - 7:33 pmORD Chicago O'Hare Intl-KOA Kona Intl

16h 13m2 stops San Diego Honolulu

8:49 am - 5:56 amKOA Kona Intl-ORD Chicago O'Hare Intl

17h 07m2 stops Honolulu Seattle/Tacoma Intl

$791Multiple Airlines

Thu, Nov 12 - Sun, Nov 22

6:05 am - 1:40 pmMDW Chicago Midway-KOA Kona Intl

11h 35m1 stop Las Vegas Harry Reid Intl

9:00 am - 5:45 amKOA Kona Intl-MDW Chicago Midway

16h 45m1 stop Sacramento Intl

$836Southwest

Sat, Nov 14 - Sat, Nov 21

5:25 am - 1:40 pmMDW Chicago Midway-KOA Kona Intl

12h 15m1 stop Las Vegas Harry Reid Intl

9:30 pm - 1:35 pmKOA Kona Intl-MDW Chicago Midway

12h 05m1 stop Las Vegas Harry Reid Intl

$836Southwest

Fri, Nov 13 - Fri, Nov 20

7:05 am - 2:41 pmORD Chicago O'Hare Intl-KOA Kona Intl

11h 36m1 stop Salt Lake City

9:45 pm - 1:37 pmKOA Kona Intl-ORD Chicago O'Hare Intl

11h 52m1 stop Seattle/Tacoma Intl

$836Delta

Sat, Nov 14 - Sat, Nov 21

7:05 am - 2:41 pmORD Chicago O'Hare Intl-KOA Kona Intl

11h 36m1 stop Salt Lake City

10:45 pm - 1:37 pmKOA Kona Intl-ORD Chicago O'Hare Intl

10h 52m1 stop Los Angeles

$836Delta

Sat, Nov 14 - Sun, Nov 15

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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 12

ORD8:00 amChicago O'Hare Intl

13h 53m

1 stop

KOA5:53 pmKona Intl

Jan 26

KOA8:40 amKona Intl

11h 19m

1 stop

ORD11:59 pmChicago O'Hare Intl

$576

Alaska Airlines

Jan 26

ORD2:13 pmChicago O'Hare Intl

30h 37m

1 stop

KOA4:50 pmKona Intl

Feb 2

KOA10:34 amKona Intl

22h 41m

1 stop

ORD1:15 pmChicago O'Hare Intl

$577

Alaska Airlines

Jan 27

ORD8:00 amChicago O'Hare Intl

13h 53m

1 stop

KOA5:53 pmKona Intl

Feb 2

KOA8:40 amKona Intl

11h 19m

1 stop

ORD11:59 pmChicago O'Hare Intl

$578

Delta flights from Chicago to Kailua-Kona

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

Delta

Jan 12

ORD6:00 amChicago O'Hare Intl

18h 00m

2 stops

KOA8:00 pmKona Intl

Jan 27

KOA10:45 pmKona Intl

11h 08m

1 stop

ORD1:53 pmChicago O'Hare Intl

$584

Delta

Jan 26

ORD7:15 amChicago O'Hare Intl

16h 45m

2 stops

KOA8:00 pmKona Intl

Feb 2

KOA9:40 pmKona Intl

15h 17m

2 stops

ORD4:57 pmChicago O'Hare Intl

$589

Delta

Jan 13

MDW12:44 pmChicago Midway

30h 13m

2 stops

KOA2:57 pmKona Intl

Jan 26

KOA10:45 pmKona Intl

14h 08m

2 stops

MDW4:53 pmChicago Midway

$610

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

Tue 1/26

8:00 am-5:53 pm

1 stop13h 53m

Kona Intl

Tue 2/2

5:54 pm-1:13 pm

2 stops15h 19m

$566

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Mon 2/1

8:00 am-5:53 pm

1 stop13h 53m

Kona Intl

Thu 2/11

6:00 am-11:59 pm

2 stops13h 59m

$575

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Tue 1/12

8:00 am-5:53 pm

1 stop13h 53m

Kona Intl

Tue 1/26

8:40 am-11:59 pm

1 stop11h 19m

$576

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Tue 1/26

8:00 am-5:53 pm

1 stop13h 53m

Kona Intl

Tue 2/2

8:40 am-11:59 pm

1 stop11h 19m

$576

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Mon 1/18

7:15 am-2:57 pm

1 stop11h 42m

Kona Intl

Fri 1/22

10:45 pm-1:53 pm

1 stop11h 08m

$578

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Mon 1/18

7:15 am-2:57 pm

1 stop11h 42m

Kona Intl

Thu 1/21

10:45 pm-1:53 pm

1 stop11h 08m

$578

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Tue 1/26

7:20 am-4:37 pm

1 stop13h 17m

Kona Intl

Tue 2/2

9:59 pm-2:36 pm

1 stop12h 37m

$646

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Wed 2/10

7:20 am-4:37 pm

1 stop13h 17m

Kona Intl

Tue 2/16

10:48 pm-1:19 pm

1 stop10h 31m

$646

Quickest round-trip

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Sat 1/9

11:00 am-4:19 pm

Nonstop9h 19m

Kona Intl

Mon 1/18

3:13 pm-5:36 am

1 stop10h 23m

$870

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Wed 12/16

10:25 am-8:32 pm

1 stop14h 07m

Kona Intl

Sat 12/26

5:50 pm-5:54 am

Nonstop8h 04m

$874

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

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

Prices are currently low for flights on this route.

Typical prices usually range from $599 to $1,271.
The lowest price recently found on this route was $566.

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 $570, 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 $766 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 $607 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 47% 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 November 2026, prices for Chicago to Kailua-Kona flights are approximately 60% 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	$289
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 $289. The best round-trip flight deal from Chicago to Kailua-Kona found on momondo in the last 72 hours is $566.

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 November 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 (42% of total bookings). The next most popular airlines are United Airlines (20%), Alaska Airlines (16%), and Delta (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 13,157 reviews	Search Alaska Airlines flights
Delta	PriceFrom $424	Free Cancellation	Rating 7.8 8,712 reviews	Search Delta flights
American Airlines	PriceFrom $445	Free Cancellation	Rating 7.0 12,230 reviews	Search American Airlines flights
United Airlines	PriceFrom $614	Free Cancellation	Rating 7.3 10,485 reviews	Search United Airlines flights

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.