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.

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.

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?

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

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.

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.

$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.

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

16h 03m1 stop Seattle/Tacoma Intl

10:05 pm - 4:53 pmKOA Kona Intl-ORD Chicago O'Hare Intl

14h 48m1 stop Seattle/Tacoma Intl

$470Delta

Wed, Oct 28 - Thu, Nov 5

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

16h 03m1 stop Seattle/Tacoma Intl

10:05 pm - 1:30 pmKOA Kona Intl-ORD Chicago O'Hare Intl

11h 25m1 stop Seattle/Tacoma Intl

$470Delta

Thu, Oct 29 - Tue, Nov 3

5:10 am - 12:35 pmMDW Chicago Midway-KOA Kona Intl

12h 25m1 stop Las Vegas Harry Reid Intl

9:30 pm - 11:50 amKOA Kona Intl-MDW Chicago Midway

10h 20m1 stop Las Vegas Harry Reid Intl

$527Southwest

Thu, Oct 29 - Thu, Nov 5

5:10 am - 12:35 pmMDW Chicago Midway-KOA Kona Intl

12h 25m1 stop Las Vegas Harry Reid Intl

11:40 am - 5:45 amKOA Kona Intl-MDW Chicago Midway

14h 05m2 stops Honolulu Sacramento Intl

$536Southwest

Thu, Oct 29 - Thu, Nov 5

2:13 pm - 4:11 pmORD Chicago O'Hare Intl-KOA Kona Intl

29h 58m1 stop San Diego

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

22h 31m1 stop San Diego

$569Alaska Airlines

Tue, Jan 12 - Tue, Jan 19

2:13 pm - 4:11 pmORD Chicago O'Hare Intl-KOA Kona Intl

29h 58m1 stop San Diego

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

22h 31m1 stop San Diego

$569Alaska Airlines

Tue, Jan 26 - Thu, Feb 4

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

Wed, Jan 13 - Mon, Jan 18

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

12h 12m1 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

$636American Airlines

Mon, Nov 9 - Mon, Nov 16

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

9h 19mnonstop

2:16 pm - 6:29 amKOA Kona Intl-ORD Chicago O'Hare Intl

12h 13m1 stop Los Angeles

$854United Airlines

Sat, Jan 9 - Mon, Jan 18

8:40 am - 4:50 pmORD Chicago O'Hare Intl-KOA Kona Intl

12h 10m1 stop Denver Intl

6:05 pm - 6:07 amKOA Kona Intl-ORD Chicago O'Hare Intl

8h 02mnonstop

$854United Airlines

Wed, Jan 27 - Sat, Feb 13

Cheap last minute flights

Enter your travel dates to find the best prices.

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

16h 03m1 stop Seattle/Tacoma Intl

9:06 pm - 4:53 pmKOA Kona Intl-ORD Chicago O'Hare Intl

14h 47m1 stop Seattle/Tacoma Intl

$714Delta

Wed, Oct 7 - Wed, Oct 14

8:29 am - 7:26 pmORD Chicago O'Hare Intl-KOA Kona Intl

15h 57m2 stops Detroit Metropolitan Wayne County Los Angeles

9:06 pm - 1:30 pmKOA Kona Intl-ORD Chicago O'Hare Intl

11h 24m1 stop Seattle/Tacoma Intl

$720Delta

Wed, Oct 7 - Wed, Oct 14

10:15 am - 9:30 pmMDW Chicago Midway-KOA Kona Intl

16h 15m2 stops San Jose Honolulu

10:00 am - 5:50 amKOA Kona Intl-MDW Chicago Midway

14h 50m1 stop Sacramento Intl

$761Southwest

Tue, Oct 6 - Thu, Oct 8

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

16h 03m1 stop Seattle/Tacoma Intl

9:06 pm - 4:53 pmKOA Kona Intl-ORD Chicago O'Hare Intl

14h 47m1 stop Seattle/Tacoma Intl

$770Delta

Wed, Oct 7 - Mon, Oct 12

10:15 am - 9:30 pmMDW Chicago Midway-KOA Kona Intl

16h 15m2 stops San Jose Honolulu

11:40 am - 5:55 amKOA Kona Intl-MDW Chicago Midway

13h 15m2 stops Honolulu Oakland

$791Southwest

Tue, Oct 6 - Thu, Oct 8

5:00 am - 2:03 pmORD Chicago O'Hare Intl-KOA Kona Intl

14h 03m1 stop Phoenix Sky Harbor Intl

6:57 pm - 9:30 amKOA Kona Intl-ORD Chicago O'Hare Intl

10h 33m1 stop Dallas/Fort Worth

$871American Airlines

Thu, Oct 8 - Tue, Jan 5

5:00 am - 2:03 pmORD Chicago O'Hare Intl-KOA Kona Intl

14h 03m1 stop Phoenix Sky Harbor Intl

3:33 pm - 3:59 pmKOA Kona Intl-ORD Chicago O'Hare Intl

19h 26m1 stop Los Angeles

$1,076American Airlines

Wed, Oct 7 - Mon, Oct 12

9:40 pm - 9:27 pmORD Chicago O'Hare Intl-KOA Kona Intl

28h 47m1 stop San Francisco

1:08 pm - 4:45 amKOA Kona Intl-ORD Chicago O'Hare Intl

10h 37m1 stop Los Angeles

$3,514United Airlines

Wed, Oct 7 - Mon, Oct 12

9:40 pm - 11:46 amORD Chicago O'Hare Intl-KOA Kona Intl

19h 06m2 stops San Francisco Los Angeles

1:08 pm - 5:45 amKOA Kona Intl-ORD Chicago O'Hare Intl

11h 37m1 stop Los Angeles

$3,519United Airlines

Wed, Oct 7 - Mon, Oct 12

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

12h 23m1 stop San Diego

11:41 am - 1:18 pmKOA Kona Intl-ORD Chicago O'Hare Intl

20h 37m1 stop Portland

$3,665Alaska Airlines

Wed, Oct 7 - Mon, Oct 12

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Delta flights from Chicago to Kailua-Kona

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

Delta

Oct 28

ORD6:35 amChicago O'Hare Intl

16h 03m

1 stop

KOA5:38 pmKona Intl

Nov 5

KOA10:05 pmKona Intl

14h 48m

1 stop

ORD4:53 pmChicago O'Hare Intl

$470

Delta

Oct 28

ORD6:20 amChicago O'Hare Intl

16h 18m

2 stops

KOA5:38 pmKona Intl

Nov 2

KOA10:05 pmKona Intl

11h 25m

1 stop

ORD1:30 pmChicago O'Hare Intl

$476

Delta

Oct 28

ORD6:20 amChicago O'Hare Intl

16h 18m

2 stops

KOA5:38 pmKona Intl

Nov 3

KOA10:05 pmKona Intl

18h 25m

2 stops

ORD8:30 pmChicago O'Hare Intl

$481

Southwest flights from Chicago to Kailua-Kona

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

Southwest

Oct 29

MDW5:10 amChicago Midway

12h 25m

1 stop

KOA12:35 pmKona Intl

Nov 5

KOA9:30 pmKona Intl

10h 20m

1 stop

MDW11:50 amChicago Midway

$527

Southwest

Oct 29

MDW5:10 amChicago Midway

12h 25m

1 stop

KOA12:35 pmKona Intl

Nov 5

KOA11:40 amKona Intl

14h 05m

2 stops

MDW5:45 amChicago Midway

$536

Southwest

Oct 29

MDW9:50 amChicago Midway

16h 40m

2 stops

KOA9:30 pmKona Intl

Nov 5

KOA11:40 amKona Intl

14h 05m

2 stops

MDW5:45 amChicago Midway

$578

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

Wed 10/28

6:35 am-5:38 pm

1 stop16h 03m

Kona Intl

Thu 11/5

10:05 pm-4:53 pm

1 stop14h 48m

$470

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Thu 10/29

6:35 am-5:38 pm

1 stop16h 03m

Kona Intl

Tue 11/3

10:05 pm-1:30 pm

1 stop11h 25m

$470

ChicagoKailua-Kona

MDW Chicago Midway - KOA Kona Intl

MDWKOA

Chicago Midway

Thu 10/29

5:10 am-12:35 pm

1 stop12h 25m

Kona Intl

Thu 11/5

9:30 pm-11:50 am

1 stop10h 20m

$527

ChicagoKailua-Kona

MDW Chicago Midway - KOA Kona Intl

MDWKOA

Chicago Midway

Thu 10/29

5:10 am-12:35 pm

1 stop12h 25m

Kona Intl

Thu 11/5

11:40 am-5:45 am

2 stops14h 05m

$536

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Tue 1/12

2:13 pm-4:11 pm

1 stop29h 58m

Kona Intl

Tue 1/19

10:44 am-1:15 pm

1 stop22h 31m

$569

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Tue 1/26

2:13 pm-4:11 pm

1 stop29h 58m

Kona Intl

Thu 2/4

10:44 am-1:15 pm

1 stop22h 31m

$569

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Wed 1/13

7:20 am-4:37 pm

1 stop13h 17m

Kona Intl

Mon 1/18

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

Mon 11/9

6:50 am-3:02 pm

1 stop12h 12m

Kona Intl

Mon 11/16

10:21 pm-1:40 pm

1 stop11h 19m

$636

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

2:16 pm-6:29 am

1 stop12h 13m

$854

Quickest round-trip

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Wed 1/27

8:40 am-4:50 pm

1 stop12h 10m

Kona Intl

Sat 2/13

6:05 pm-6:07 am

Nonstop8h 02m

$854

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 low for flights on this route.

Typical prices usually range from $554 to $822.
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 $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	$235
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 $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 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 (20%), 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
Delta	PriceFrom $403	Free Cancellation	Rating 7.8 8,627 reviews	Search Delta flights
Alaska Airlines	PriceFrom $403	Free Cancellation	Rating 7.9 13,008 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $445	Free Cancellation	Rating 7.0 12,128 reviews	Search American Airlines flights
United Airlines	PriceFrom $447	Free Cancellation	Rating 7.4 10,280 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 $447 round-trip, up to an average price of $944. 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.