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

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

Los Angeles (LAX) was the most common stop: 32% 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 August 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.

$217 Cheap Flights from Chicago to Kailua-Kona in 2026

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.

7:35 am - 3:00 pmORD Chicago O'Hare Intl-KOA Kona Intl

11h 25m1 stop Salt Lake City

8:55 pm - 12:03 pmKOA Kona Intl-ORD Chicago O'Hare Intl

11h 08m1 stop Salt Lake City

$434Delta

Wed, Nov 11 - Tue, Nov 17

6:45 am - 7:27 pmORD Chicago O'Hare Intl-KOA Kona Intl

16h 42m1 stop Seattle/Tacoma Intl

8:55 pm - 12:03 pmKOA Kona Intl-ORD Chicago O'Hare Intl

11h 08m1 stop Salt Lake City

$434Delta

Sun, Nov 15 - Thu, Dec 3

6:00 am - 3:17 pmORD Chicago O'Hare Intl-KOA Kona Intl

14h 17m1 stop Los Angeles Los Angeles

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

11h 19m1 stop Phoenix Sky Harbor Intl

$434American Airlines

Wed, Oct 28 - Tue, Nov 3

5:00 am - 3:02 pmORD Chicago O'Hare Intl-KOA Kona Intl

14h 02m1 stop Phoenix Sky Harbor Intl

10:21 pm - 2:43 pmKOA Kona Intl-ORD Chicago O'Hare Intl

12h 22m1 stop Phoenix Sky Harbor Intl

$434American Airlines

Wed, Dec 2 - Wed, Dec 9

2:15 pm - 3:52 pmORD Chicago O'Hare Intl-KOA Kona Intl

29h 37m1 stop San Diego

11:34 am - 1:17 pmKOA Kona Intl-ORD Chicago O'Hare Intl

21h 43m1 stop San Diego

$434Alaska Airlines

Sun, Nov 1 - Wed, Nov 4

7:57 pm - 3:52 pmORD Chicago O'Hare Intl-KOA Kona Intl

23h 55m1 stop San Diego

11:34 am - 1:17 pmKOA Kona Intl-ORD Chicago O'Hare Intl

21h 43m1 stop San Diego

$434Alaska Airlines

Sun, Nov 1 - Wed, Nov 4

2:21 pm - 3:52 pmORD Chicago O'Hare Intl-KOA Kona Intl

30h 31m1 stop San Diego

6:31 pm - 6:59 pmKOA Kona Intl-ORD Chicago O'Hare Intl

20h 28m2 stops Honolulu San Diego

$439Multiple Airlines

Sat, Oct 31 - Thu, Nov 12

7:57 pm - 3:52 pmORD Chicago O'Hare Intl-KOA Kona Intl

23h 55m1 stop San Diego

8:45 pm - 6:59 pmKOA Kona Intl-ORD Chicago O'Hare Intl

18h 14m2 stops Honolulu San Diego

$439Multiple Airlines

Sun, Nov 1 - Wed, Nov 4

7:15 am - 4:54 pmORD Chicago O'Hare Intl-KOA Kona Intl

13h 39m1 stop Denver Intl

5:50 pm - 6:00 amKOA Kona Intl-ORD Chicago O'Hare Intl

8h 10mnonstop

$774United Airlines

Tue, Jan 12 - Sat, Jan 16

11:15 am - 4:14 pmORD Chicago O'Hare Intl-KOA Kona Intl

8h 59mnonstop

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

8h 04mnonstop

$795United Airlines

Sat, Dec 12 - Sat, Dec 19

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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 3

KOA7:05 pmKona Intl

13h 30m

2 stops

MDW12:35 pmChicago Midway

$470

Southwest

Nov 26

MDW6:05 amChicago Midway

11h 30m

1 stop

KOA1:35 pmKona Intl

Dec 3

KOA9:30 pmKona Intl

12h 40m

1 stop

MDW2:10 pmChicago Midway

$494

Southwest

Oct 28

MDW6:05 amChicago Midway

11h 30m

1 stop

KOA12:35 pmKona Intl

Nov 3

KOA9:30 pmKona Intl

15h 50m

2 stops

MDW5:20 pmChicago Midway

$500

American Airlines flights from Chicago to Kailua-Kona

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

American Airlines

Sep 15

ORD6:55 amChicago O'Hare Intl

14h 05m

1 stop

KOA4:00 pmKona Intl

Sep 22

KOA9:45 pmKona Intl

20h 58m

1 stop

ORD11:43 pmChicago O'Hare Intl

$492

American Airlines

Nov 8

ORD5:00 amChicago O'Hare Intl

15h 29m

2 stops

KOA4:29 pmKona Intl

Nov 17

KOA10:21 pmKona Intl

18h 34m

1 stop

ORD8:55 pmChicago O'Hare Intl

$497

American Airlines

Sep 18

ORD8:23 amChicago O'Hare Intl

12h 37m

1 stop

KOA4:00 pmKona Intl

Sep 27

KOA3:34 pmKona Intl

13h 34m

2 stops

ORD10:08 amChicago O'Hare Intl

$500

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 11/11

7:35 am-3:00 pm

1 stop11h 25m

Kona Intl

Tue 11/17

8:55 pm-12:03 pm

1 stop11h 08m

$434

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Sun 11/15

6:45 am-7:27 pm

1 stop16h 42m

Kona Intl

Thu 12/3

8:55 pm-12:03 pm

1 stop11h 08m

$434

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Wed 10/28

6:00 am-3:17 pm

1 stop14h 17m

Kona Intl

Tue 11/3

10:21 pm-1:40 pm

1 stop11h 19m

$434

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Wed 12/2

5:00 am-3:02 pm

1 stop14h 02m

Kona Intl

Wed 12/9

10:21 pm-2:43 pm

1 stop12h 22m

$434

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Sun 11/1

2:15 pm-3:52 pm

1 stop29h 37m

Kona Intl

Wed 11/4

11:34 am-1:17 pm

1 stop21h 43m

$434

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Sun 11/1

7:57 pm-3:52 pm

1 stop23h 55m

Kona Intl

Wed 11/4

11:34 am-1:17 pm

1 stop21h 43m

$434

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Sat 10/31

2:21 pm-3:52 pm

1 stop30h 31m

Kona Intl

Thu 11/12

6:31 pm-6:59 pm

2 stops20h 28m

$439

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Sun 11/1

7:57 pm-3:52 pm

1 stop23h 55m

Kona Intl

Wed 11/4

8:45 pm-6:59 pm

2 stops18h 14m

$439

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Tue 1/12

7:15 am-4:54 pm

1 stop13h 39m

Kona Intl

Sat 1/16

5:50 pm-6:00 am

Nonstop8h 10m

$774

Quickest round-trip

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Sat 12/12

11:15 am-4:14 pm

Nonstop8h 59m

Kona Intl

Sat 12/19

5:50 pm-5:54 am

Nonstop8h 04m

$795

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 $613 to $770.
The lowest price recently found on this route was $434.

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 $539, 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 $597.

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 $725 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 $549 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 48% 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 August 2026, prices for Chicago to Kailua-Kona flights are approximately 22% 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	$217
Fastest flight time	9h 17m
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 $217. The best round-trip flight deal from Chicago to Kailua-Kona found on momondo in the last 72 hours is $434.

The fastest flight from Chicago to Kailua-Kona takes 9h 17m

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 17m.
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 August 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 (38% of total bookings). The next most popular airlines are United Airlines (23%), Delta (17%), 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 $350	Free Cancellation	Rating 7.8 8,519 reviews	Search Delta flights
Alaska Airlines	PriceFrom $418	Free Cancellation	Rating 7.9 12,833 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $445	Free Cancellation	Rating 7.1 11,989 reviews	Search American Airlines flights
United Airlines	PriceFrom $447	Free Cancellation	Rating 7.4 10,109 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.