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

Flights via Los Angeles (LAX) offer the lowest average round-trip price of $456.

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

Southwest and Alaska Airlines 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?

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

What airlines fly to Kailua-Kona?

American Airlines, Alaska Airlines and United 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 53% of people opting to fly with this airline when traveling to Kailua-Kona. Keep in mind that there are 6 different airlines that fly to Kailua-Kona on a routine basis, so you have a few additional options to choose from.

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 6 as of March 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.

$213 Cheap Flights from Chicago to Kailua-Kona in 2026

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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.

3:52 pm - 10:57 am

ORD

KOA

24h 05m

2 stops

1:16 pm - 1:13 pm

KOA

ORD

18h 57m

1 stop

$415Multiple Airlines

Tue, Apr 28 - Tue, May 5

8:00 am - 7:52 pm

ORD

KOA

16h 52m

1 stop

1:16 pm - 1:13 pm

KOA

ORD

18h 57m

1 stop

$425Alaska Airlines

Tue, Apr 28 - Tue, May 5

8:50 am - 7:16 pm

ORD

KOA

15h 26m

2 stops

1:16 pm - 1:13 pm

KOA

ORD

18h 57m

1 stop

$444Multiple Airlines

Thu, Apr 30 - Mon, May 4

7:59 pm - 2:59 pm

ORD

KOA

24h 00m

1 stop

1:16 pm - 1:13 pm

KOA

ORD

18h 57m

1 stop

$458Alaska Airlines

Thu, Apr 16 - Thu, Apr 30

7:59 pm - 2:20 pm

ORD

KOA

23h 21m

2 stops

1:16 pm - 7:03 pm

KOA

ORD

24h 47m

1 stop

$461Multiple Airlines

Mon, Apr 20 - Mon, Apr 27

8:50 am - 10:16 pm

ORD

KOA

18h 26m

2 stops

1:16 pm - 1:13 pm

KOA

ORD

18h 57m

1 stop

$467Multiple Airlines

Mon, Apr 27 - Fri, May 1

5:45 am - 1:15 pm

MDW

KOA

12h 30m

1 stop

10:00 am - 5:40 am

KOA

MDW

14h 40m

1 stop

$531Southwest

Sun, Apr 19 - Sat, Apr 25

5:10 am - 1:15 pm

MDW

KOA

13h 05m

1 stop

10:00 am - 5:45 am

KOA

MDW

14h 45m

1 stop

$534Southwest

Mon, Apr 13 - Thu, Apr 23

7:16 pm - 5:43 pm

MDW

KOA

27h 27m

2 stops

8:50 pm - 9:06 am

KOA

MDW

31h 16m

2 stops

$556Delta

Tue, Apr 14 - Thu, Apr 23

9:27 am - 7:03 pm

MDW

KOA

14h 36m

2 stops

8:50 pm - 9:06 am

KOA

MDW

31h 16m

2 stops

$564Delta

Fri, Apr 17 - Thu, Apr 23

Alaska Airlines flights from Chicago to Kailua-Kona

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

Alaska Airlines

Apr 28

ORD8:00 amChicago O'Hare Intl

16h 52m

1 stop

KOA7:52 pmKona Intl

May 5

KOA1:16 pmKona Intl

18h 57m

1 stop

ORD1:13 pmChicago O'Hare Intl

$425

Alaska Airlines

Apr 16

ORD7:59 pmChicago O'Hare Intl

24h 00m

1 stop

KOA2:59 pmKona Intl

Apr 30

KOA1:16 pmKona Intl

18h 57m

1 stop

ORD1:13 pmChicago O'Hare Intl

$458

Alaska Airlines

Apr 22

ORD3:52 pmChicago O'Hare Intl

22h 44m

2 stops

KOA9:36 amKona Intl

May 1

KOA1:16 pmKona Intl

24h 47m

1 stop

ORD7:03 pmChicago O'Hare Intl

$473

Southwest flights from Chicago to Kailua-Kona

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

Southwest

Apr 24

ORD6:15 amChicago O'Hare Intl

16h 50m

2 stops

KOA6:05 pmKona Intl

Apr 28

KOA8:25 pmKona Intl

12h 30m

1 stop

ORD1:55 pmChicago O'Hare Intl

$507

Southwest

Apr 19

MDW5:45 amChicago Midway

12h 30m

1 stop

KOA1:15 pmKona Intl

Apr 25

KOA10:00 amKona Intl

14h 40m

1 stop

MDW5:40 amChicago Midway

$531

Southwest

Apr 13

MDW5:10 amChicago Midway

13h 05m

1 stop

KOA1:15 pmKona Intl

Apr 23

KOA10:00 amKona Intl

14h 45m

1 stop

MDW5:45 amChicago Midway

$534

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 4/28

3:52 pm-10:57 am

2 stops24h 05m

Kona Intl

Tue 5/5

1:16 pm-1:13 pm

1 stop18h 57m

$415

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 4/28

8:00 am-7:52 pm

1 stop16h 52m

Kona Intl

Tue 5/5

1:16 pm-1:13 pm

1 stop18h 57m

$425

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 4/30

8:50 am-7:16 pm

2 stops15h 26m

Kona Intl

Mon 5/4

1:16 pm-1:13 pm

1 stop18h 57m

$444

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 4/16

7:59 pm-2:59 pm

1 stop24h 00m

Kona Intl

Thu 4/30

1:16 pm-1:13 pm

1 stop18h 57m

$458

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 4/20

7:59 pm-2:20 pm

2 stops23h 21m

Kona Intl

Mon 4/27

1:16 pm-7:03 pm

1 stop24h 47m

$461

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 4/27

8:50 am-10:16 pm

2 stops18h 26m

Kona Intl

Fri 5/1

1:16 pm-1:13 pm

1 stop18h 57m

$467

Quickest round-trip

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Sun 4/19

5:45 am-1:15 pm

1 stop12h 30m

Kona Intl

Sat 4/25

10:00 am-5:40 am

1 stop14h 40m

$531

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 4/13

5:10 am-1:15 pm

1 stop13h 05m

Kona Intl

Thu 4/23

10:00 am-5:45 am

1 stop14h 45m

$534

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 4/14

7:16 pm-5:43 pm

2 stops27h 27m

Kona Intl

Thu 4/23

8:50 pm-9:06 am

2 stops31h 16m

$556

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Fri 4/17

9:27 am-7:03 pm

2 stops14h 36m

Kona Intl

Thu 4/23

8:50 pm-9:06 am

2 stops31h 16m

$564

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 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 $530, are often lower during this time because this is during the off-season. The month of September is another great option to travel to Kailua-Kona, with average flight prices from Chicago averaging around $568.

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 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 $727 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 $595 on momondo.

What cabin class options are available on Chicago to Kona Intl flights?

There are 3 cabin classes available to choose from on Chicago to Kona Intl 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 32% 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 March 2026, prices for Chicago to Kailua-Kona flights are approximately 69% 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	$1,344
Fastest flight time	9h 13m
Direct flights	Sun
Airports in Kailua-Kona	1 airport

The best flight deal from Chicago to Kailua-Kona found on momondo in the last 72 hours is $1,344

The fastest flight from Chicago to Kailua-Kona takes 9h 13m

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

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 13m.
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 6 as of March 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 (46% of total bookings). The next most popular airlines are United Airlines (16%), 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
Delta	PriceFrom $350	Free Cancellation	Rating 7.9 8,291 reviews	Search Delta flights
Alaska Airlines	PriceFrom $418	Free Cancellation	Rating 8.0 12,042 reviews	Search Alaska Airlines flights
Hawaiian Airlines	PriceFrom $429	Free Cancellation	Rating 7.8 2,839 reviews	Search Hawaiian Airlines flights
Southwest	PriceFrom $442	Free Cancellation	Rating 8.0 4,317 reviews	Search Southwest flights
American Airlines	PriceFrom $447	Free Cancellation	Rating 7.1 11,464 reviews	Search American Airlines flights
United Airlines	PriceFrom $447	Free Cancellation	Rating 7.4 9,422 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.