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?

Seattle (SEA) was the most common stop: 33% of momondo users choosing 1-stop flights on this route connected there.

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

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

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 49% of people opting to fly with this airline when traveling to Kailua-Kona. Keep in mind that there are 5 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 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.

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 5 as of May 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.

$266 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 $763 to $678. The lowest price recently found on this route was $505.

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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.

8:50 pm - 12:40 pm

MDW

KOA

20h 50m

2 stops

10:00 am - 5:45 am

KOA

MDW

14h 45m

1 stop

$505Southwest

Wed, Sep 23 - Wed, Sep 30

8:50 pm - 12:40 pm

MDW

KOA

20h 50m

2 stops

10:00 am - 5:45 am

KOA

MDW

14h 45m

2 stops

$510Southwest

Wed, Sep 23 - Wed, Sep 30

8:50 pm - 12:25 pm

MDW

KOA

20h 35m

2 stops

10:00 am - 5:45 am

KOA

MDW

14h 45m

1 stop

$535Southwest

Wed, Aug 19 - Tue, Aug 25

6:00 am - 11:42 am

ORD

KOA

10h 42m

1 stop

1:52 pm - 5:53 am

KOA

ORD

11h 01m

1 stop

$536United Airlines

Tue, Jun 2 - Tue, Jun 9

3:28 pm - 10:14 pm

ORD

KOA

11h 46m

1 stop

8:00 am - 11:59 pm

KOA

ORD

10h 59m

1 stop

$540Alaska Airlines

Mon, Jun 1 - Mon, Jun 8

8:20 pm - 12:25 pm

MDW

KOA

21h 05m

2 stops

10:00 am - 5:40 am

KOA

MDW

14h 40m

2 stops

$540Southwest

Wed, Aug 19 - Tue, Aug 25

7:40 am - 2:40 pm

ORD

KOA

12h 00m

1 stop

9:20 am - 6:20 am

KOA

ORD

16h 00m

2 stops

$545Multiple Airlines

Wed, Jun 3 - Mon, Jun 8

8:42 am - 7:20 pm

ORD

KOA

15h 38m

2 stops

8:50 pm - 4:45 pm

KOA

ORD

14h 55m

1 stop

$546Delta

Tue, Jun 2 - Tue, Jun 9

9:25 am - 7:20 pm

ORD

KOA

14h 55m

2 stops

8:50 pm - 8:31 pm

KOA

ORD

18h 41m

2 stops

$551Delta

Tue, Jun 2 - Tue, Jun 9

6:00 am - 11:42 am

ORD

KOA

10h 42m

1 stop

7:00 am - 10:59 pm

KOA

ORD

10h 59m

1 stop

$570United Airlines

Tue, Jun 2 - Tue, Jun 9

Southwest flights from Chicago to Kailua-Kona

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

Southwest

Aug 6

MDW5:40 amChicago Midway

13h 30m

2 stops

KOA2:10 pmKona Intl

Aug 17

KOA10:00 amKona Intl

14h 45m

1 stop

MDW5:45 amChicago Midway

$777

Southwest

May 14

MDW7:50 amChicago Midway

15h 15m

2 stops

KOA6:05 pmKona Intl

May 22

KOA10:00 amKona Intl

14h 45m

1 stop

MDW5:45 amChicago Midway

$785

Southwest

May 14

MDW5:10 amChicago Midway

13h 05m

1 stop

KOA1:15 pmKona Intl

May 22

KOA10:00 amKona Intl

14h 45m

1 stop

MDW5:45 amChicago Midway

$790

United Airlines flights from Chicago to Kailua-Kona

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

United Airlines

Jun 2

ORD6:00 amChicago O'Hare Intl

10h 42m

1 stop

KOA11:42 amKona Intl

Jun 9

KOA1:52 pmKona Intl

11h 01m

1 stop

ORD5:53 amChicago O'Hare Intl

$536

United Airlines

Jun 2

ORD6:00 amChicago O'Hare Intl

10h 42m

1 stop

KOA11:42 amKona Intl

Jun 9

KOA7:00 amKona Intl

10h 59m

1 stop

ORD10:59 pmChicago O'Hare Intl

$570

United Airlines

Jun 4

ORD6:13 amChicago O'Hare Intl

11h 24m

1 stop

KOA12:37 pmKona Intl

Jun 9

KOA1:52 pmKona Intl

11h 01m

1 stop

ORD5:53 amChicago O'Hare Intl

$577

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 9/23

8:50 pm-12:40 pm

2 stops20h 50m

Kona Intl

Wed 9/30

10:00 am-5:45 am

1 stop14h 45m

$505

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 9/23

8:50 pm-12:40 pm

2 stops20h 50m

Kona Intl

Wed 9/30

10:00 am-5:45 am

2 stops14h 45m

$510

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 8/19

8:50 pm-12:25 pm

2 stops20h 35m

Kona Intl

Tue 8/25

10:00 am-5:45 am

1 stop14h 45m

$535

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 6/2

6:00 am-11:42 am

1 stop10h 42m

Kona Intl

Tue 6/9

1:52 pm-5:53 am

1 stop11h 01m

$536

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 6/1

3:28 pm-10:14 pm

1 stop11h 46m

Kona Intl

Mon 6/8

8:00 am-11:59 pm

1 stop10h 59m

$540

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 8/19

8:20 pm-12:25 pm

2 stops21h 05m

Kona Intl

Tue 8/25

10:00 am-5:40 am

2 stops14h 40m

$540

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 6/3

7:40 am-2:40 pm

1 stop12h 00m

Kona Intl

Mon 6/8

9:20 am-6:20 am

2 stops16h 00m

$545

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 6/2

8:42 am-7:20 pm

2 stops15h 38m

Kona Intl

Tue 6/9

8:50 pm-4:45 pm

1 stop14h 55m

$546

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 6/2

9:25 am-7:20 pm

2 stops14h 55m

Kona Intl

Tue 6/9

8:50 pm-8:31 pm

2 stops18h 41m

$551

Quickest round-trip

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 6/2

6:00 am-11:42 am

1 stop10h 42m

Kona Intl

Tue 6/9

7:00 am-10:59 pm

1 stop10h 59m

$570

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?

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 $722 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.

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 May 2026, prices for Chicago to Kailua-Kona flights are approximately 57% 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 42m
Direct flights	None

The fastest flight from Chicago to Kailua-Kona takes 10h 42m

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 42m.
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 5 as of May 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 (42% of total bookings). The next most popular airlines are United Airlines (19%), 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 $343	Free Cancellation	Rating 7.9 8,451 reviews	Search Delta flights
Alaska Airlines	PriceFrom $418	Free Cancellation	Rating 7.9 12,352 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $442	Free Cancellation	Rating 8.0 4,298 reviews	Search Southwest flights
American Airlines	PriceFrom $447	Free Cancellation	Rating 7.1 11,667 reviews	Search American Airlines flights
United Airlines	PriceFrom $447	Free Cancellation	Rating 7.4 9,699 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.