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.

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

Los Angeles (LAX) was the most common stop: 31% of momondo users choosing 1-stop flights on this route connected there.

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

San Francisco (SFO) has the shortest average layover time for this route: 0h 56m.

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.

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

Flights via San Francisco (SFO) offer the lowest average round-trip price of $487.

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

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 September 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.

$235 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.

7:20 am - 2:43 pmORD Chicago O'Hare Intl-KOA Kona Intl

12h 23m1 stop San Diego

10:36 am - 1:25 pmKOA Kona Intl-ORD Chicago O'Hare Intl

21h 49m1 stop San Diego

$470Alaska Airlines

Mon, Oct 19 - Wed, Oct 28

7:20 am - 2:43 pmORD Chicago O'Hare Intl-KOA Kona Intl

12h 23m1 stop San Diego

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

13h 29m1 stop Seattle/Tacoma Intl

$470Alaska Airlines

Wed, Oct 21 - Wed, Oct 28

7:49 pm - 2:43 pmORD Chicago O'Hare Intl-KOA Kona Intl

23h 54m1 stop San Diego

6:31 pm - 6:53 pmKOA Kona Intl-ORD Chicago O'Hare Intl

19h 22m2 stops Honolulu San Diego

$475Multiple Airlines

Mon, Oct 19 - Wed, Oct 28

7:49 pm - 2:48 pmORD Chicago O'Hare Intl-KOA Kona Intl

23h 59m1 stop San Diego

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

19h 44m2 stops Honolulu San Diego

$475Multiple Airlines

Sun, Oct 25 - Thu, Nov 12

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

16h 03m1 stop Seattle/Tacoma Intl

10:02 pm - 6:10 pmKOA Kona Intl-ORD Chicago O'Hare Intl

15h 08m2 stops Los Angeles Salt Lake City

$476Delta

Wed, Oct 21 - Wed, Oct 28

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

16h 03m1 stop Seattle/Tacoma Intl

9:06 pm - 6:10 pmKOA Kona Intl-ORD Chicago O'Hare Intl

16h 04m2 stops Seattle/Tacoma Intl Salt Lake City

$476Delta

Thu, Oct 22 - Wed, Oct 28

6:50 am - 3:02 pmORD Chicago O'Hare Intl-KOA Kona Intl

12h 12m1 stop Phoenix Sky Harbor Intl

10:09 pm - 3:00 pmKOA Kona Intl-ORD Chicago O'Hare Intl

12h 51m1 stop Phoenix Sky Harbor Intl

$538American Airlines

Tue, Nov 17 - Wed, Nov 25

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

13h 00m1 stop Phoenix Sky Harbor Intl

9:59 pm - 2:50 pmKOA Kona Intl-ORD Chicago O'Hare Intl

12h 51m1 stop Phoenix Sky Harbor Intl

$538American Airlines

Wed, Jan 27 - Tue, Feb 2

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

9h 11mnonstop

8:25 pm - 11:42 amKOA Kona Intl-ORD Chicago O'Hare Intl

11h 17m1 stop Denver Intl

$834United Airlines

Sat, Feb 27 - Thu, Mar 4

11:15 am - 4:16 pmORD Chicago O'Hare Intl-KOA Kona Intl

9h 01mnonstop

11:55 pm - 2:39 pmKOA Kona Intl-ORD Chicago O'Hare Intl

10h 44m1 stop San Francisco

$834United Airlines

Sat, Dec 5 - Tue, Dec 8

Cheap last minute flights

Enter your travel dates to find the best prices.

1:03 pm - 1:28 pmORD Chicago O'Hare Intl-KOA Kona Intl

29h 25m1 stop Seattle/Tacoma Intl

8:00 am - 6:20 amKOA Kona Intl-ORD Chicago O'Hare Intl

17h 20m2 stops Lihue Seattle/Tacoma Intl

$670Multiple Airlines

Thu, Sep 24 - Sat, Sep 26

9:59 am - 7:15 pmMDW Chicago Midway-KOA Kona Intl

14h 16m2 stops Minneapolis St Paul Los Angeles

10:02 pm - 6:00 pmKOA Kona Intl-MDW Chicago Midway

14h 58m2 stops Los Angeles Detroit Metropolitan Wayne County

$751Delta

Mon, Sep 28 - Tue, Oct 6

2:22 pm - 11:06 amORD Chicago O'Hare Intl-KOA Kona Intl

25h 44m1 stop Portland

12:51 pm - 6:20 amKOA Kona Intl-ORD Chicago O'Hare Intl

12h 29m2 stops Kahului Seattle/Tacoma Intl

$755Multiple Airlines

Tue, Sep 22 - Sat, Sep 26

6:10 am - 7:15 pmORD Chicago O'Hare Intl-KOA Kona Intl

18h 05m2 stops Minneapolis St Paul Los Angeles

8:55 pm - 6:26 pmKOA Kona Intl-ORD Chicago O'Hare Intl

16h 31m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County

$761Delta

Tue, Sep 22 - Sat, Sep 26

7:20 am - 6:17 pmORD Chicago O'Hare Intl-KOA Kona Intl

15h 57m2 stops San Diego Honolulu

8:00 am - 6:20 amKOA Kona Intl-ORD Chicago O'Hare Intl

17h 20m2 stops Lihue Seattle/Tacoma Intl

$761Multiple Airlines

Thu, Sep 24 - Sat, Sep 26

9:59 am - 7:15 pmMDW Chicago Midway-KOA Kona Intl

14h 16m2 stops Minneapolis St Paul Los Angeles

10:02 pm - 6:00 pmKOA Kona Intl-MDW Chicago Midway

14h 58m2 stops Los Angeles Detroit Metropolitan Wayne County

$800Delta

Mon, Sep 28 - Tue, Oct 6

8:23 am - 4:00 pmORD Chicago O'Hare Intl-KOA Kona Intl

12h 37m1 stop Los Angeles

3:34 pm - 12:22 pmKOA Kona Intl-ORD Chicago O'Hare Intl

15h 48m1 stop Los Angeles

$853American Airlines

Thu, Sep 24 - Sat, Sep 26

7:00 am - 5:31 pmORD Chicago O'Hare Intl-KOA Kona Intl

15h 31m1 stop Seattle/Tacoma Intl

8:55 pm - 6:01 pmKOA Kona Intl-ORD Chicago O'Hare Intl

16h 06m1 stop Seattle/Tacoma Intl

$861Delta

Tue, Sep 22 - Sat, Sep 26

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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

Oct 25

ORD7:49 pmChicago O'Hare Intl

23h 59m

1 stop

KOA2:48 pmKona Intl

Nov 12

KOA11:34 amKona Intl

21h 43m

1 stop

ORD1:17 pmChicago O'Hare Intl

$470

Alaska Airlines

Oct 17

ORD2:14 pmChicago O'Hare Intl

25h 27m

1 stop

KOA10:41 amKona Intl

Oct 23

KOA10:36 amKona Intl

21h 49m

1 stop

ORD1:25 pmChicago O'Hare Intl

$504

Alaska Airlines

Jan 26

ORD2:13 pmChicago O'Hare Intl

29h 58m

1 stop

KOA4:11 pmKona Intl

Feb 4

KOA10:44 amKona Intl

22h 31m

1 stop

ORD1:15 pmChicago O'Hare Intl

$537

Southwest flights from Chicago to Kailua-Kona

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

Southwest

Oct 25

MDW5:15 amChicago Midway

17h 55m

2 stops

KOA6:10 pmKona Intl

Nov 12

KOA9:30 pmKona Intl

10h 20m

1 stop

MDW11:50 amChicago Midway

$526

Southwest

Oct 25

MDW5:15 amChicago Midway

17h 55m

2 stops

KOA6:10 pmKona Intl

Nov 12

KOA9:30 pmKona Intl

13h 45m

2 stops

MDW3:15 pmChicago Midway

$531

Southwest

Feb 4

MDW10:15 amChicago Midway

15h 10m

2 stops

KOA9:25 pmKona Intl

Feb 11

KOA9:00 amKona Intl

16h 45m

1 stop

MDW5:45 amChicago Midway

$546

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 10/19

7:20 am-2:43 pm

1 stop12h 23m

Kona Intl

Wed 10/28

10:36 am-1:25 pm

1 stop21h 49m

$470

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Wed 10/21

7:20 am-2:43 pm

1 stop12h 23m

Kona Intl

Wed 10/28

10:21 pm-4:50 pm

1 stop13h 29m

$470

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Mon 10/19

7:49 pm-2:43 pm

1 stop23h 54m

Kona Intl

Wed 10/28

6:31 pm-6:53 pm

2 stops19h 22m

$475

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Sun 10/25

7:49 pm-2:48 pm

1 stop23h 59m

Kona Intl

Thu 11/12

7:15 pm-6:59 pm

2 stops19h 44m

$475

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Wed 10/21

6:35 am-5:38 pm

1 stop16h 03m

Kona Intl

Wed 10/28

10:02 pm-6:10 pm

2 stops15h 08m

$476

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Thu 10/22

6:35 am-5:38 pm

1 stop16h 03m

Kona Intl

Wed 10/28

9:06 pm-6:10 pm

2 stops16h 04m

$476

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Tue 11/17

6:50 am-3:02 pm

1 stop12h 12m

Kona Intl

Wed 11/25

10:09 pm-3:00 pm

1 stop12h 51m

$538

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Wed 1/27

7:20 am-4:20 pm

1 stop13h 00m

Kona Intl

Tue 2/2

9:59 pm-2:50 pm

1 stop12h 51m

$538

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Sat 2/27

11:00 am-4:11 pm

Nonstop9h 11m

Kona Intl

Thu 3/4

8:25 pm-11:42 am

1 stop11h 17m

$834

Quickest round-trip

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Sat 12/5

11:15 am-4:16 pm

Nonstop9h 01m

Kona Intl

Tue 12/8

11:55 pm-2:39 pm

1 stop10h 44m

$834

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 $561 to $790.
The lowest price recently found on this route was $470.

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 $546, 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 $593.

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 $744 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 $547 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 43% 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 September 2026, prices for Chicago to Kailua-Kona flights are approximately 18% 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	$235
Fastest flight time	9h 11m
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 $235. The best round-trip flight deal from Chicago to Kailua-Kona found on momondo in the last 72 hours is $470.

The fastest flight from Chicago to Kailua-Kona takes 9h 11m

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 11m.
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 September 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 (39% of total bookings). The next most popular airlines are United Airlines (21%), Delta (18%), and Alaska Airlines (15%).

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
Delta	PriceFrom $403	Free Cancellation	Rating 7.8 8,597 reviews	Search Delta flights
Alaska Airlines	PriceFrom $403	Free Cancellation	Rating 7.9 12,953 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $445	Free Cancellation	Rating 7.0 12,076 reviews	Search American Airlines flights
United Airlines	PriceFrom $447	Free Cancellation	Rating 7.4 10,222 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.