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 47% 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.

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

As of October 2026, 6 flights take off from Chicago and land in Kailua-Kona each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

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 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.

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.

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.

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

Alaska Airlines, Delta, and Southwest 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 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.

$298 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.

6:05 am - 1:35 pmMDW Chicago Midway-KOA Kona Intl

11h 30m1 stop Las Vegas Harry Reid Intl

9:30 pm - 12:15 pmKOA Kona Intl-MDW Chicago Midway

10h 45m1 stop Las Vegas Harry Reid Intl

$559Southwest

Thu, Nov 26 - Fri, Dec 4

2:11 pm - 11:10 amORD Chicago O'Hare Intl-KOA Kona Intl

24h 59m2 stops Portland Los Angeles

4:15 pm - 1:13 pmKOA Kona Intl-ORD Chicago O'Hare Intl

16h 58m2 stops Honolulu Portland

$562Multiple Airlines

Tue, Jan 26 - Tue, Feb 2

8:00 am - 10:29 pmORD Chicago O'Hare Intl-KOA Kona Intl

18h 29m1 stop Seattle/Tacoma Intl

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

10h 52m1 stop Seattle/Tacoma Intl

$564Alaska Airlines

Thu, Jan 21 - Thu, Jan 28

8:00 am - 10:29 pmORD Chicago O'Hare Intl-KOA Kona Intl

18h 29m1 stop Seattle/Tacoma Intl

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

11h 08m1 stop Seattle/Tacoma Intl

$564Alaska Airlines

Tue, Feb 2 - Tue, Feb 9

7:00 am - 6:54 pmORD Chicago O'Hare Intl-KOA Kona Intl

15h 54m1 stop Seattle/Tacoma Intl

10:45 pm - 1:31 pmKOA Kona Intl-ORD Chicago O'Hare Intl

10h 46m1 stop Seattle/Tacoma Intl

$566Delta

Wed, Jan 27 - Wed, Feb 3

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

$566Delta

Fri, Nov 13 - Tue, Nov 17

8:57 pm - 1:26 pmORD Chicago O'Hare Intl-KOA Kona Intl

20h 29m1 stop Los Angeles

3:07 pm - 12:30 pmKOA Kona Intl-ORD Chicago O'Hare Intl

17h 23m1 stop Los Angeles

$617American Airlines

Wed, Jan 13 - Mon, Jan 18

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

13h 17m1 stop Phoenix Sky Harbor Intl

3:07 pm - 12:30 pmKOA Kona Intl-ORD Chicago O'Hare Intl

17h 23m1 stop Los Angeles

$620American Airlines

Tue, Jan 26 - Thu, Feb 4

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

$860United Airlines

Sat, Jan 30 - Thu, Feb 4

11:15 am - 4:32 pmORD Chicago O'Hare Intl-KOA Kona Intl

9h 17mnonstop

8:25 pm - 11:18 amKOA Kona Intl-ORD Chicago O'Hare Intl

10h 53m1 stop Denver Intl

$864United Airlines

Sat, Feb 13 - Thu, Feb 18

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Southwest flights from Chicago to Kailua-Kona

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

Southwest

Nov 26

MDW6:05 amChicago Midway

11h 30m

1 stop

KOA1:35 pmKona Intl

Dec 4

KOA9:30 pmKona Intl

10h 45m

1 stop

MDW12:15 pmChicago Midway

$559

Southwest

Nov 26

MDW6:05 amChicago Midway

11h 30m

1 stop

KOA1:35 pmKona Intl

Dec 4

KOA9:30 pmKona Intl

13h 20m

2 stops

MDW2:50 pmChicago Midway

$565

Southwest

Feb 25

MDW6:55 amChicago Midway

12h 00m

1 stop

KOA2:55 pmKona Intl

Mar 1

KOA7:05 pmKona Intl

13h 30m

2 stops

MDW12:35 pmChicago Midway

$609

Alaska Airlines flights from Chicago to Kailua-Kona

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

Alaska Airlines

Jan 26

ORD8:00 amChicago O'Hare Intl

18h 29m

1 stop

KOA10:29 pmKona Intl

Feb 2

KOA11:29 pmKona Intl

10h 52m

1 stop

ORD2:21 pmChicago O'Hare Intl

$564

Alaska Airlines

Jan 10

ORD8:00 amChicago O'Hare Intl

13h 22m

1 stop

KOA5:22 pmKona Intl

Jan 31

KOA11:29 pmKona Intl

18h 39m

2 stops

ORD10:08 pmChicago O'Hare Intl

$575

Alaska Airlines

Nov 14

ORD9:30 amChicago O'Hare Intl

12h 23m

1 stop

KOA5:53 pmKona Intl

Nov 21

KOA9:04 pmKona Intl

28h 52m

1 stop

ORD5:56 amChicago O'Hare Intl

$601

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKailua-Kona

MDW Chicago Midway - KOA Kona Intl

MDWKOA

Chicago Midway

Thu 11/26

6:05 am-1:35 pm

1 stop11h 30m

Kona Intl

Fri 12/4

9:30 pm-12:15 pm

1 stop10h 45m

$559

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Tue 1/26

2:11 pm-11:10 am

2 stops24h 59m

Kona Intl

Tue 2/2

4:15 pm-1:13 pm

2 stops16h 58m

$562

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Thu 1/21

8:00 am-10:29 pm

1 stop18h 29m

Kona Intl

Thu 1/28

11:29 pm-2:21 pm

1 stop10h 52m

$564

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Tue 2/2

8:00 am-10:29 pm

1 stop18h 29m

Kona Intl

Tue 2/9

8:51 am-11:59 pm

1 stop11h 08m

$564

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Wed 1/27

7:00 am-6:54 pm

1 stop15h 54m

Kona Intl

Wed 2/3

10:45 pm-1:31 pm

1 stop10h 46m

$566

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Fri 11/13

6:40 am-7:25 pm

1 stop16h 45m

Kona Intl

Tue 11/17

9:45 pm-1:37 pm

1 stop11h 52m

$566

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Wed 1/13

8:57 pm-1:26 pm

1 stop20h 29m

Kona Intl

Mon 1/18

3:07 pm-12:30 pm

1 stop17h 23m

$617

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

Thu 2/4

3:07 pm-12:30 pm

1 stop17h 23m

$620

Quickest round-trip

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Sat 1/30

11:00 am-4:19 pm

Nonstop9h 19m

Kona Intl

Thu 2/4

3:13 pm-5:36 am

1 stop10h 23m

$860

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Sat 2/13

11:15 am-4:32 pm

Nonstop9h 17m

Kona Intl

Thu 2/18

8:25 pm-11:18 am

1 stop10h 53m

$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 $554 to $764.
The lowest price recently found on this route was $559.

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 $602.

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 $775 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 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 October 2026, prices for Chicago to Kailua-Kona flights are approximately 6% 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	$298
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 $298. The best round-trip flight deal from Chicago to Kailua-Kona found on momondo in the last 72 hours is $559.

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 (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
Alaska Airlines	PriceFrom $403	Free Cancellation	Rating 7.9 13,034 reviews	Search Alaska Airlines flights
Delta	PriceFrom $424	Free Cancellation	Rating 7.8 8,634 reviews	Search Delta flights
American Airlines	PriceFrom $445	Free Cancellation	Rating 7.0 12,137 reviews	Search American Airlines flights
United Airlines	PriceFrom $563	Free Cancellation	Rating 7.4 10,309 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 6 flights/week on average for this route. A good United Airlines flight deal for Chicago to Kailua-Kona starts from $563 round-trip, up to an average price of $978. Our users have rated United Airlines at 7.4/10.

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.