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

As of June 2026, 5 flights take off from Chicago and land in Kailua-Kona each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.

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

Seattle (SEA) was the most common stop: 33% 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 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 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.

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

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

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 offers the lowest fares from Chicago to Kailua-Kona?

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

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 June 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.

$337 Cheap Flights from Chicago to Kailua-Kona in 2026

Q: 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 $937 to $753. The lowest price recently found on this route was $434.

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Kailua-Kona

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:45 am - 2:00 pm

MDW

KOA

12h 15m

1 stop

9:30 pm - 2:05 pm

KOA

MDW

12h 35m

1 stop

$434Southwest

Tue, Nov 10 - Tue, Nov 17

2:55 pm - 6:34 pm

ORD

KOA

32h 39m

1 stop

9:55 pm - 5:33 pm

KOA

ORD

14h 38m

1 stop

$440Delta

Wed, Sep 9 - Tue, Sep 15

6:30 pm - 6:34 pm

ORD

KOA

29h 04m

1 stop

9:55 pm - 5:33 pm

KOA

ORD

14h 38m

1 stop

$456Delta

Wed, Sep 9 - Sun, Sep 20

7:35 am - 6:34 pm

ORD

KOA

15h 59m

1 stop

9:55 pm - 11:21 pm

KOA

ORD

20h 26m

1 stop

$471Delta

Thu, Sep 10 - Wed, Sep 16

2:55 pm - 6:34 pm

ORD

KOA

32h 39m

1 stop

9:55 pm - 11:21 pm

KOA

ORD

20h 26m

1 stop

$472Delta

Sat, Sep 12 - Wed, Sep 16

2:55 pm - 6:34 pm

ORD

KOA

32h 39m

1 stop

9:55 pm - 1:44 pm

KOA

ORD

10h 49m

1 stop

$477Delta

Wed, Sep 9 - Thu, Sep 17

2:55 pm - 6:34 pm

ORD

KOA

32h 39m

1 stop

9:03 pm - 1:31 pm

KOA

ORD

11h 28m

1 stop

$493Delta

Thu, Sep 10 - Thu, Sep 17

6:30 pm - 6:34 pm

ORD

KOA

29h 04m

1 stop

9:55 pm - 5:33 pm

KOA

ORD

14h 38m

1 stop

$494Delta

Tue, Sep 8 - Tue, Sep 15

7:00 am - 5:35 pm

ORD

KOA

15h 35m

1 stop

10:05 pm - 9:30 pm

KOA

ORD

18h 25m

2 stops

$499Delta

Tue, Aug 11 - Wed, Aug 26

6:50 am - 12:40 pm

MDW

KOA

10h 50m

1 stop

10:00 am - 5:45 am

KOA

MDW

14h 45m

1 stop

$549Southwest

Tue, Aug 25 - Fri, Sep 4

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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

Nov 2

ORD2:25 pmChicago O'Hare Intl

24h 09m

2 stops

KOA10:34 amKona Intl

Nov 9

KOA4:52 pmKona Intl

22h 08m

2 stops

ORD7:00 pmChicago O'Hare Intl

$515

Alaska Airlines

Oct 27

ORD2:21 pmChicago O'Hare Intl

24h 15m

2 stops

KOA9:36 amKona Intl

Nov 10

KOA4:52 pmKona Intl

22h 08m

2 stops

ORD7:00 pmChicago O'Hare Intl

$546

Alaska Airlines

Oct 27

ORD2:21 pmChicago O'Hare Intl

24h 15m

2 stops

KOA9:36 amKona Intl

Nov 10

KOA4:52 pmKona Intl

22h 08m

2 stops

ORD7:00 pmChicago O'Hare Intl

$557

Southwest flights from Chicago to Kailua-Kona

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

Southwest

Nov 10

MDW5:45 amChicago Midway

12h 15m

1 stop

KOA2:00 pmKona Intl

Nov 17

KOA9:30 pmKona Intl

12h 35m

1 stop

MDW2:05 pmChicago Midway

$434

Southwest

Aug 25

MDW6:50 amChicago Midway

10h 50m

1 stop

KOA12:40 pmKona Intl

Sep 4

KOA10:00 amKona Intl

14h 45m

1 stop

MDW5:45 amChicago Midway

$549

Southwest

Aug 26

MDW8:20 pmChicago Midway

21h 05m

2 stops

KOA12:25 pmKona Intl

Sep 4

KOA10:00 amKona Intl

14h 45m

1 stop

MDW5:45 amChicago Midway

$560

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 11/10

5:45 am-2:00 pm

1 stop12h 15m

Kona Intl

Tue 11/17

9:30 pm-2:05 pm

1 stop12h 35m

$434

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 9/9

2:55 pm-6:34 pm

1 stop32h 39m

Kona Intl

Tue 9/15

9:55 pm-5:33 pm

1 stop14h 38m

$440

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 9/9

6:30 pm-6:34 pm

1 stop29h 04m

Kona Intl

Sun 9/20

9:55 pm-5:33 pm

1 stop14h 38m

$456

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 9/10

7:35 am-6:34 pm

1 stop15h 59m

Kona Intl

Wed 9/16

9:55 pm-11:21 pm

1 stop20h 26m

$471

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sat 9/12

2:55 pm-6:34 pm

1 stop32h 39m

Kona Intl

Wed 9/16

9:55 pm-11:21 pm

1 stop20h 26m

$472

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 9/9

2:55 pm-6:34 pm

1 stop32h 39m

Kona Intl

Thu 9/17

9:55 pm-1:44 pm

1 stop10h 49m

$477

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 9/10

2:55 pm-6:34 pm

1 stop32h 39m

Kona Intl

Thu 9/17

9:03 pm-1:31 pm

1 stop11h 28m

$493

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 9/8

6:30 pm-6:34 pm

1 stop29h 04m

Kona Intl

Tue 9/15

9:55 pm-5:33 pm

1 stop14h 38m

$494

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 8/11

7:00 am-5:35 pm

1 stop15h 35m

Kona Intl

Wed 8/26

10:05 pm-9:30 pm

2 stops18h 25m

$499

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 8/25

6:50 am-12:40 pm

1 stop10h 50m

Kona Intl

Fri 9/4

10:00 am-5:45 am

1 stop14h 45m

$549

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?

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 $262, are often lower during this time because this is during the off-season. The month of March is another great option to travel to Kailua-Kona, with average flight prices from Chicago averaging around $265.

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 $718 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 $597 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 29% 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 June 2026, prices for Chicago to Kailua-Kona flights are approximately 51% 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

Fastest flight time	10h 50m
Direct flights	None

The fastest flight from Chicago to Kailua-Kona takes 10h 50m

There are no direct flights from Chicago to Kailua-Kona. There are no popular flight routes from Chicago to Kailua-Kona.

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 10h 50m.
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 June 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 (21%), Alaska Airlines (18%), and Delta (14%).

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 $371	Free Cancellation	Rating 7.9 8,397 reviews	Search Delta flights
Alaska Airlines	PriceFrom $418	Free Cancellation	Rating 7.9 12,478 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $447	Free Cancellation	Rating 7.1 11,636 reviews	Search American Airlines flights
United Airlines	PriceFrom $447	Free Cancellation	Rating 7.4 9,808 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 5 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 $912. 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.