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Cheap flights from Chicago to Kailua-Kona from $211

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 1/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to Kailua-Kona

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
9:00 am - 3:27 pm
ORD
-
KOA
34h 27m1 stop
Alaska Airlines Logo
2:51 pm - 2:29 pm
KOA
-
ORD
19h 38m1 stop
$382Alaska Airlines
Wed, Jan 21 - Tue, Feb 3
Alaska Airlines Logo
9:00 am - 3:27 pm
ORD
-
KOA
34h 27m1 stop
Alaska Airlines Logo
2:51 pm - 11:37 pm
KOA
-
ORD
28h 46m1 stop
$390Alaska Airlines
Wed, Jan 28 - Wed, Feb 4
Alaska Airlines Logo
3:44 pm - 3:27 pm
ORD
-
KOA
27h 43m1 stop
Alaska Airlines Logo
2:51 pm - 2:29 pm
KOA
-
ORD
19h 38m1 stop
$391Alaska Airlines
Wed, Jan 21 - Thu, Feb 5
Delta Logo
2:20 pm - 6:47 pm
ORD
-
KOA
32h 27m1 stop
Delta Logo
9:55 pm - 1:22 pm
KOA
-
ORD
11h 27m1 stop
$393Delta
Sun, Jan 25 - Sat, Feb 7
Delta Logo
7:40 am - 7:39 pm
ORD
-
KOA
15h 59m1 stop
Delta Logo
9:55 pm - 1:22 pm
KOA
-
ORD
11h 27m1 stop
$394Delta
Mon, Feb 23 - Sat, Feb 28
Alaska Airlines Logo
3:07 pm - 3:53 pm
ORD
-
KOA
28h 46m1 stop
Alaska Airlines Logo
12:10 pm - 7:02 pm
KOA
-
ORD
25h 52m1 stop
$396Alaska Airlines
Tue, Mar 3 - Tue, Mar 17
Alaska Airlines Logo
3:44 pm - 3:27 pm
ORD
-
KOA
27h 43m1 stop
Alaska Airlines Logo
2:24 pm - 11:37 pm
KOA
-
ORD
29h 13m1 stop
$397Alaska Airlines
Tue, Feb 3 - Mon, Feb 9
Alaska Airlines Logo
9:00 am - 3:27 pm
ORD
-
KOA
34h 27m1 stop
Alaska Airlines Logo
2:24 pm - 2:29 pm
KOA
-
ORD
20h 05m1 stop
$398Alaska Airlines
Tue, Jan 20 - Mon, Feb 2
Multiple Airlines Logo
3:44 pm - 8:28 pm
ORD
-
KOA
32h 44m2 stops
Multiple Airlines Logo
2:24 pm - 11:37 pm
KOA
-
ORD
29h 13m1 stop
$402Multiple Airlines
Tue, Feb 3 - Mon, Feb 9
Delta Logo
7:40 am - 7:39 pm
ORD
-
KOA
15h 59m1 stop
Delta Logo
8:55 pm - 11:51 pm
KOA
-
ORD
21h 56m1 stop
$403Delta
Mon, Feb 23 - Thu, Mar 12

Alaska Airlines flights from Chicago to Kailua-Kona

Our best Alaska Airlines deals on Chicago to Kailua-Kona flight tickets
Alaska Airlines
Jan 21
ORD9:00 amChicago O'Hare Intl
34h 27m
1 stop
KOA3:27 pmKona Intl
Feb 3
KOA2:51 pmKona Intl
19h 38m
1 stop
ORD2:29 pmChicago O'Hare Intl
$382
Find similar
Alaska Airlines
Jan 28
ORD9:00 amChicago O'Hare Intl
34h 27m
1 stop
KOA3:27 pmKona Intl
Feb 4
KOA2:51 pmKona Intl
28h 46m
1 stop
ORD11:37 pmChicago O'Hare Intl
$390
Find similar
Alaska Airlines
Jan 21
ORD3:44 pmChicago O'Hare Intl
27h 43m
1 stop
KOA3:27 pmKona Intl
Feb 5
KOA2:51 pmKona Intl
19h 38m
1 stop
ORD2:29 pmChicago O'Hare Intl
$391
Find similar

American Airlines flights from Chicago to Kailua-Kona

Our best American Airlines deals on Chicago to Kailua-Kona flight tickets
American Airlines
Jan 15
ORD7:00 amChicago O'Hare Intl
11h 54m
1 stop
KOA2:54 pmKona Intl
Jan 22
KOA9:44 pmKona Intl
10h 48m
1 stop
ORD12:32 pmChicago O'Hare Intl
$580
Find similar
American Airlines
Jan 14
ORD7:00 amChicago O'Hare Intl
11h 54m
1 stop
KOA2:54 pmKona Intl
Jan 23
KOA9:44 pmKona Intl
13h 13m
1 stop
ORD2:57 pmChicago O'Hare Intl
$610
Find similar
American Airlines
Jan 7
ORD7:00 amChicago O'Hare Intl
11h 54m
1 stop
KOA2:54 pmKona Intl
Jan 13
KOA7:45 pmKona Intl
11h 09m
1 stop
ORD10:54 amChicago O'Hare Intl
$694
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Kailua-Kona that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated January 1, 2026.
Use the filters below to find and compare flights from Chicago to Kailua-Kona that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 1/21

9:00 am-3:27 pm

1 stop34h 27m

Kona Intl

Tue 2/3

2:51 pm-2:29 pm

1 stop19h 38m

$382

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 1/28

9:00 am-3:27 pm

1 stop34h 27m

Kona Intl

Wed 2/4

2:51 pm-11:37 pm

1 stop28h 46m

$390

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 1/21

3:44 pm-3:27 pm

1 stop27h 43m

Kona Intl

Thu 2/5

2:51 pm-2:29 pm

1 stop19h 38m

$391

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sun 1/25

2:20 pm-6:47 pm

1 stop32h 27m

Kona Intl

Sat 2/7

9:55 pm-1:22 pm

1 stop11h 27m

$393

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 2/23

7:40 am-7:39 pm

1 stop15h 59m

Kona Intl

Sat 2/28

9:55 pm-1:22 pm

1 stop11h 27m

$394

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 3/3

3:07 pm-3:53 pm

1 stop28h 46m

Kona Intl

Tue 3/17

12:10 pm-7:02 pm

1 stop25h 52m

$396

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 2/3

3:44 pm-3:27 pm

1 stop27h 43m

Kona Intl

Mon 2/9

2:24 pm-11:37 pm

1 stop29h 13m

$397

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 1/20

9:00 am-3:27 pm

1 stop34h 27m

Kona Intl

Mon 2/2

2:24 pm-2:29 pm

1 stop20h 05m

$398

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 2/3

3:44 pm-8:28 pm

2 stops32h 44m

Kona Intl

Mon 2/9

2:24 pm-11:37 pm

1 stop29h 13m

$402

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 2/23

7:40 am-7:39 pm

1 stop15h 59m

Kona Intl

Thu 3/12

8:55 pm-11:51 pm

1 stop21h 56m

$403

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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?

The cheapest month to fly to Kailua-Kona from Chicago is in September. Flight prices, which tend to average around $563, 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 $584.

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 $730 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 $606 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 21% 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 January 2026, prices for Chicago to Kailua-Kona flights are approximately 16% cheaper 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 04m

Direct flights

Sun

Airports in Kailua-Kona

1 airport
The fastest flight from Chicago to Kailua-Kona takes 9h 04m
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 04m.

  • 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?

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $371Free CancellationRating
7.9
8,017 reviews
Search Delta flights
Alaska AirlinesPriceFrom $424Free CancellationRating
8.0
11,597 reviews
Search Alaska Airlines flights
Hawaiian AirlinesPriceFrom $429Free CancellationRating
7.8
2,823 reviews
Search Hawaiian Airlines flights
United AirlinesPriceFrom $447Free CancellationRating
7.4
9,132 reviews
Search United Airlines flights
American AirlinesPriceFrom $452Free CancellationRating
7.2
11,072 reviews
Search American Airlines flights
SouthwestPriceFrom $593Free CancellationRating
8.0
4,252 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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