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Cheap flights from Chicago to Kailua-Kona from $202

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 3/4. 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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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.
Delta Logo
7:40 am - 7:39 pm
ORD
-
KOA
15h 59m
1 stop
Delta Logo
8:55 pm - 1:24 pm
KOA
-
ORD
11h 29m
1 stop
$364Delta
Mon, Mar 2 - Tue, Mar 10
Delta Logo
7:40 am - 6:30 pm
ORD
-
KOA
14h 50m
2 stops
Delta Logo
9:55 pm - 1:22 pm
KOA
-
ORD
11h 27m
1 stop
$370Delta
Wed, Feb 18 - Wed, Feb 25
Delta Logo
7:40 am - 6:30 pm
ORD
-
KOA
14h 50m
2 stops
Delta Logo
9:55 pm - 1:22 pm
KOA
-
ORD
11h 27m
1 stop
$390Delta
Wed, Feb 18 - Wed, Feb 25
Delta Logo
7:00 am - 6:55 pm
ORD
-
KOA
16h 55m
1 stop
Delta Logo
8:55 pm - 5:06 pm
KOA
-
ORD
15h 11m
1 stop
$394Delta
Thu, Apr 30 - Mon, May 4
Delta Logo
7:10 am - 6:37 pm
ORD
-
KOA
16h 27m
2 stops
Delta Logo
8:55 pm - 1:25 pm
KOA
-
ORD
11h 30m
1 stop
$400Delta
Mon, Mar 9 - Wed, Mar 18
Alaska Airlines Logo
5:29 pm - 10:57 pm
ORD
-
KOA
33h 28m
1 stop
Alaska Airlines Logo
1:10 pm - 11:59 pm
KOA
-
ORD
30h 49m
1 stop
$403Alaska Airlines
Mon, Mar 2 - Wed, Mar 4
Alaska Airlines Logo
5:29 pm - 10:57 pm
ORD
-
KOA
33h 28m
1 stop
Alaska Airlines Logo
10:17 pm - 12:01 pm
KOA
-
ORD
33h 44m
1 stop
$404Alaska Airlines
Fri, Feb 27 - Wed, Mar 4
Multiple Airlines Logo
8:20 am - 2:59 pm
ORD
-
KOA
11h 39m
1 stop
Multiple Airlines Logo
1:40 pm - 2:41 pm
KOA
-
ORD
20h 01m
2 stops
$408Multiple Airlines
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
6:10 am - 1:45 pm
MDW
-
KOA
11h 35m
1 stop
Southwest Logo
9:25 pm - 3:00 pm
KOA
-
MDW
13h 35m
1 stop
$669Southwest
Wed, Feb 4 - Thu, Feb 12
Southwest Logo
8:25 am - 9:20 pm
MDW
-
KOA
16h 55m
2 stops
Southwest Logo
9:25 pm - 3:00 pm
KOA
-
MDW
13h 35m
1 stop
$675Southwest
Wed, Feb 4 - Thu, Feb 12

American Airlines flights from Chicago to Kailua-Kona

Our best American Airlines deals on Chicago to Kailua-Kona flight tickets
American Airlines
Feb 18
ORD11:31 amChicago O'Hare Intl
11h 28m
1 stop
KOA6:59 pmKona Intl
Feb 25
KOA6:30 pmKona Intl
11h 15m
1 stop
ORD9:45 amChicago O'Hare Intl
$422
American Airlines
Feb 18
ORD8:26 amChicago O'Hare Intl
14h 33m
2 stops
KOA6:59 pmKona Intl
Feb 25
KOA10:11 pmKona Intl
10h 20m
1 stop
ORD12:31 pmChicago O'Hare Intl
$428
American Airlines
Feb 18
ORD9:25 amChicago O'Hare Intl
13h 34m
1 stop
KOA6:59 pmKona Intl
Feb 23
KOA10:11 pmKona Intl
11h 22m
1 stop
ORD1:33 pmChicago O'Hare Intl
$465

Alaska Airlines flights from Chicago to Kailua-Kona

Our best Alaska Airlines deals on Chicago to Kailua-Kona flight tickets
Alaska Airlines
Mar 2
ORD5:29 pmChicago O'Hare Intl
33h 28m
1 stop
KOA10:57 pmKona Intl
Mar 4
KOA1:10 pmKona Intl
30h 49m
1 stop
ORD11:59 pmChicago O'Hare Intl
$403
Alaska Airlines
Feb 27
ORD5:29 pmChicago O'Hare Intl
33h 28m
1 stop
KOA10:57 pmKona Intl
Mar 4
KOA10:17 pmKona Intl
33h 44m
1 stop
ORD12:01 pmChicago O'Hare Intl
$404
Alaska Airlines
Feb 18
ORD7:00 amChicago O'Hare Intl
19h 57m
1 stop
KOA10:57 pmKona Intl
Feb 25
KOA1:10 pmKona Intl
21h 48m
1 stop
ORD2:58 pmChicago O'Hare Intl
$413

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 23, 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

Mon 3/2

7:40 am-7:39 pm

1 stop15h 59m

Kona Intl

Tue 3/10

8:55 pm-1:24 pm

1 stop11h 29m

$364

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 2/18

7:40 am-6:30 pm

2 stops14h 50m

Kona Intl

Wed 2/25

9:55 pm-1:22 pm

1 stop11h 27m

$370

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 2/18

7:40 am-6:30 pm

2 stops14h 50m

Kona Intl

Wed 2/25

9:55 pm-1:22 pm

1 stop11h 27m

$390

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Thu 4/30

7:00 am-6:55 pm

1 stop16h 55m

Kona Intl

Mon 5/4

8:55 pm-5:06 pm

1 stop15h 11m

$394

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 3/9

7:10 am-6:37 pm

2 stops16h 27m

Kona Intl

Wed 3/18

8:55 pm-1:25 pm

1 stop11h 30m

$400

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 3/2

5:29 pm-10:57 pm

1 stop33h 28m

Kona Intl

Wed 3/4

1:10 pm-11:59 pm

1 stop30h 49m

$403

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 2/27

5:29 pm-10:57 pm

1 stop33h 28m

Kona Intl

Wed 3/4

10:17 pm-12:01 pm

1 stop33h 44m

$404

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 4/14

8:20 am-2:59 pm

1 stop11h 39m

Kona Intl

Tue 4/21

1:40 pm-2:41 pm

2 stops20h 01m

$408

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 2/4

6:10 am-1:45 pm

1 stop11h 35m

Kona Intl

Thu 2/12

9:25 pm-3:00 pm

1 stop13h 35m

$669

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 2/4

8:25 am-9:20 pm

2 stops16h 55m

Kona Intl

Thu 2/12

9:25 pm-3:00 pm

1 stop13h 35m

$675

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 $591, 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 $593.

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 $719 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 $599 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 9% 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 5% 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

$1,194

Fastest flight time

9h 04m

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 $1,194
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 $343Free CancellationRating
7.9
8,110 reviews
Search Delta flights
Alaska AirlinesPriceFrom $419Free CancellationRating
8.0
11,785 reviews
Search Alaska Airlines flights
Hawaiian AirlinesPriceFrom $429Free CancellationRating
7.8
2,829 reviews
Search Hawaiian Airlines flights
United AirlinesPriceFrom $447Free CancellationRating
7.4
9,194 reviews
Search United Airlines flights
American AirlinesPriceFrom $453Free CancellationRating
7.2
11,193 reviews
Search American Airlines flights
SouthwestPriceFrom $578Free CancellationRating
8.0
4,268 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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