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

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

Which layover airport has the shortest travel time from Chicago to Kailua-Kona?

Flights connecting via Phoenix (PHX) have the shortest average one-way travel time: 11h 23m.

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: 52% of momondo users choosing 1-stop flights on this route connected there.

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 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 October 2025.

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.

$181 Cheap Flights from Chicago to Kailua-Kona in 2025/26

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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.

9:00 am - 3:27 pmORD-KOA

34h 27m1 stop

2:24 pm - 11:37 pmKOA-ORD

29h 13m1 stop

$383Alaska Airlines

Find Deal

mié., ene. 21 - lun., ene. 26

3:49 pm - 3:27 pmORD-KOA

27h 38m1 stop

7:40 pm - 11:37 pmKOA-ORD

23h 57m2 stops

$389Alaska Airlines

Find Deal

mié., ene. 21 - lun., ene. 26

9:00 am - 6:26 amORD-KOA

25h 26m2 stops

2:24 pm - 2:29 pmKOA-ORD

20h 05m1 stop

$390Alaska Airlines

Find Deal

mar., ene. 13 - lun., ene. 26

3:05 pm - 4:00 pmORD-KOA

28h 55m1 stop

2:20 pm - 11:59 pmKOA-ORD

29h 39m1 stop

$391Alaska Airlines

Find Deal

mar., dic. 9 - mié., dic. 17

7:00 am - 2:54 pmORD-KOA

11h 54m1 stop

10:35 pm - 2:05 pmKOA-ORD

11h 30m1 stop

$423American Airlines

Find Deal

mié., feb. 11 - mié., feb. 18

7:30 am - 7:50 pmORD-KOA

16h 20m1 stop

8:55 pm - 11:44 pmKOA-ORD

21h 49m1 stop

$424Delta

Find Deal

dom., mar. 1 - mar., mar. 10

7:50 am - 6:20 pmORD-KOA

14h 30m1 stop

9:30 pm - 4:57 pmKOA-ORD

15h 27m2 stops

$428Delta

Find Deal

mar., dic. 9 - lun., dic. 15

7:00 am - 2:54 pmORD-KOA

11h 54m1 stop

6:30 pm - 9:53 amKOA-ORD

11h 23m1 stop

$453American Airlines

Find Deal

jue., ene. 15 - dom., ene. 25

6:10 am - 1:45 pmMDW-KOA

11h 35m1 stop

7:00 pm - 12:35 pmKOA-MDW

13h 35m2 stops

$542Southwest

Find Deal

mié., ene. 14 - jue., ene. 22

5:15 am - 6:10 pmMDW-KOA

16h 55m2 stops

9:15 pm - 11:35 amKOA-MDW

10h 20m1 stop

$569Southwest

Find Deal

mar., dic. 9 - mar., dic. 16

Southwest flights from Chicago to Kailua-Kona

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

Southwest

Jan 14

MDW6:10 amChicago Midway

11h 35m

1 stop

KOA1:45 pmKona Intl

Jan 22

KOA7:00 pmKona Intl

13h 35m

2 stops

MDW12:35 pmChicago Midway

$542

Find similar

Southwest

Nov 11

ORD7:15 amChicago O'Hare Intl

18h 05m

2 stops

KOA9:20 pmKona Intl

Nov 18

KOA9:15 pmKona Intl

14h 10m

1 stop

ORD3:25 pmChicago O'Hare Intl

$548

Find similar

Southwest

Dec 9

MDW5:15 amChicago Midway

16h 55m

2 stops

KOA6:10 pmKona Intl

Dec 16

KOA9:15 pmKona Intl

10h 20m

1 stop

MDW11:35 amChicago Midway

$569

Find similar

Delta flights from Chicago to Kailua-Kona

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

Delta

Mar 1

ORD7:30 amChicago O'Hare Intl

16h 20m

1 stop

KOA7:50 pmKona Intl

Mar 10

KOA8:55 pmKona Intl

21h 49m

1 stop

ORD11:44 pmChicago O'Hare Intl

$424

Find similar

Delta

Dec 9

ORD7:50 amChicago O'Hare Intl

14h 30m

1 stop

KOA6:20 pmKona Intl

Dec 15

KOA9:30 pmKona Intl

15h 27m

2 stops

ORD4:57 pmChicago O'Hare Intl

$428

Find similar

Delta

Dec 10

ORD8:50 amChicago O'Hare Intl

14h 40m

2 stops

KOA7:30 pmKona Intl

Dec 15

KOA9:30 pmKona Intl

15h 27m

2 stops

ORD4:57 pmChicago O'Hare Intl

$434

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mié. 1/21

9:00 am-3:27 pm

1 stop34h 27m

Kona Intl

lun. 1/26

2:24 pm-11:37 pm

1 stop29h 13m

$383

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mié. 1/21

3:49 pm-3:27 pm

1 stop27h 38m

Kona Intl

lun. 1/26

7:40 pm-11:37 pm

2 stops23h 57m

$389

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mar. 1/13

9:00 am-6:26 am

2 stops25h 26m

Kona Intl

lun. 1/26

2:24 pm-2:29 pm

1 stop20h 05m

$390

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mar. 12/9

3:05 pm-4:00 pm

1 stop28h 55m

Kona Intl

mié. 12/17

2:20 pm-11:59 pm

1 stop29h 39m

$391

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mié. 2/11

7:00 am-2:54 pm

1 stop11h 54m

Kona Intl

mié. 2/18

10:35 pm-2:05 pm

1 stop11h 30m

$423

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

dom. 3/1

7:30 am-7:50 pm

1 stop16h 20m

Kona Intl

mar. 3/10

8:55 pm-11:44 pm

1 stop21h 49m

$424

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

mar. 12/9

7:50 am-6:20 pm

1 stop14h 30m

Kona Intl

lun. 12/15

9:30 pm-4:57 pm

2 stops15h 27m

$428

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

jue. 1/15

7:00 am-2:54 pm

1 stop11h 54m

Kona Intl

dom. 1/25

6:30 pm-9:53 am

1 stop11h 23m

$453

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

mié. 1/14

6:10 am-1:45 pm

1 stop11h 35m

Kona Intl

jue. 1/22

7:00 pm-12:35 pm

2 stops13h 35m

$542

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

mar. 12/9

5:15 am-6:10 pm

2 stops16h 55m

Kona Intl

mar. 12/16

9:15 pm-11:35 am

1 stop10h 20m

$569

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 September. Flight prices, which tend to average around $577, are often lower during this time because this is during the off-season. The month of January is another great option to travel to Kailua-Kona, with average flight prices from Chicago averaging around $603.

What is the cheapest day to depart on your flight to Kailua-Kona?

The cheapest day to depart on your flight to Kailua-Kona is on a Tuesday when prices can be found for as low as $628. This is often the case because there is less demand to fly during this day of the week. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Kailua-Kona on Saturday is $1,374.

What is the cheapest time of day to depart on your flight to Kailua-Kona?

Flying to Kailua-Kona from Chicago in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $686 when looking at flights departing in the afternoon. In contrast, the most expensive time of day to depart to Kailua-Kona is in the morning when prices are around $1,374.

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 $720 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 $611 on momondo.

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

There are 4 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 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 October 2025, prices for Chicago to Kailua-Kona flights are approximately 0% 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	9h 01m
Direct flights	Sun
Airports in Kailua-Kona	1 airport

The fastest flight from Chicago to Kailua-Kona takes 9h 01m

Direct flights go from Chicago to Kailua-Kona on Sunday. The only airline offering direct flights is United Airlines.

There is 1 airport near Kailua-Kona: 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 11h 05m.
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 October 2025.
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 (16%), and Delta (12%).

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 7,995 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $429	Free Cancellation	Rating 7.8 2,794 reviews	Search Hawaiian Airlines flights
Alaska Airlines	PriceFrom $441	Free Cancellation	Rating 8.0 11,199 reviews	Search Alaska Airlines flights
United Airlines	PriceFrom $447	Free Cancellation	Rating 7.4 8,996 reviews	Search United Airlines flights
American Airlines	PriceFrom $467	Free Cancellation	Rating 7.2 11,033 reviews	Search American Airlines flights
Southwest	PriceFrom $593	Free Cancellation	Rating 8.0 4,235 reviews	Search Southwest 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.

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jue. 11/27

jue. 12/4

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Cheap flights from Chicago to Kailua-Kona from $181

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Kailua-Kona departing on 1/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

Filter for what you want

Filter for what you want

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Trusted and free

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Find the cheapest flights from Chicago to Kailua-Kona

Cheap round-trip flights

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Southwest flights from Chicago to Kailua-Kona

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

Delta flights from Chicago to Kailua-Kona

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

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See travel insights to Kailua-Kona from

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

What is the cheapest month to fly to Kailua-Kona?

What is the cheapest day to depart on your flight to Kailua-Kona?

What is the cheapest time of day to depart on your flight to Kailua-Kona?

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?

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

There are 4 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 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 October 2025, prices for Chicago to Kailua-Kona flights are approximately 0% more expensive when compared to flights at the same time last year.

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

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

What airlines fly to Kailua-Kona?

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

Seattle (SEA) was the most common stop: 52% of momondo users choosing 1-stop flights on this route connected there.

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 travel time from Chicago to Kailua-Kona?

Flights connecting via Phoenix (PHX) have the shortest average one-way travel time: 11h 23m.

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.

When to book flights from Chicago to Kailua-Kona

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

Direct flights

Airports in Kailua-Kona

How far is Chicago to Kona Intl by plane?

When did momondo last update prices for flights from Chicago to Kona Intl Airport?

How many operators does momondo search for flights from Chicago to Kona Intl Airport?

How old do you have to be to fly from Chicago to Kona Intl Airport?

What documentation or ID do you need to fly to Kona Intl Airport?

What is the most popular plane model from Chicago to Kailua-Kona?

What is the most popular airline from Chicago to Kailua-Kona?

Best airlines flying from Chicago to Kailua-Kona

Compare and see reviews for airlines that fly from Chicago to Kailua-Kona with momondo

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Kailua-Kona?

Can I find flights from Chicago to Kailua-Kona with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Kailua-Kona?

I’m not ready to book a flight from Chicago to Kailua-Kona right now. Can momondo alert me if prices change?

An easier way to manage your Kailua-Kona trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing Hawaii