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Cheap flights from Chicago to Kailua-Kona from $178

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 3/10. 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
3:07 pm - 3:53 pm
ORD
-
KOA
28h 46m
1 stop
Alaska Airlines Logo
12:10 pm - 11:59 pm
KOA
-
ORD
30h 49m
1 stop
$402Alaska Airlines
Wed, Mar 4 - Tue, Mar 10
Multiple Airlines Logo
8:20 am - 3:53 pm
ORD
-
KOA
35h 33m
1 stop
Multiple Airlines Logo
1:56 pm - 2:58 pm
KOA
-
ORD
20h 02m
2 stops
$405Multiple Airlines
Wed, Mar 4 - Mon, Mar 9
Multiple Airlines Logo
8:20 am - 10:15 pm
ORD
-
KOA
17h 55m
2 stops
Multiple Airlines Logo
12:10 pm - 2:58 pm
KOA
-
ORD
21h 48m
1 stop
$408Multiple Airlines
Mon, Mar 2 - Tue, Mar 10
Alaska Airlines Logo
3:07 pm - 2:53 pm
ORD
-
KOA
28h 46m
1 stop
Alaska Airlines Logo
12:10 pm - 11:59 pm
KOA
-
ORD
30h 49m
1 stop
$412Alaska Airlines
Sun, Mar 8 - Thu, Mar 12
American Airlines Logo
5:00 am - 3:30 pm
ORD
-
KOA
14h 30m
1 stop
American Airlines Logo
10:40 pm - 3:05 pm
KOA
-
ORD
12h 25m
1 stop
$422American Airlines
Wed, Feb 25 - Wed, Mar 4
Delta Logo
7:40 am - 7:39 pm
ORD
-
KOA
15h 59m
1 stop
Delta Logo
9:55 pm - 1:22 pm
KOA
-
ORD
11h 27m
1 stop
$424Delta
Mon, Feb 23 - Thu, Mar 5
Multiple Airlines Logo
3:07 pm - 3:53 pm
ORD
-
KOA
28h 46m
1 stop
Multiple Airlines Logo
9:01 pm - 2:58 pm
KOA
-
ORD
12h 57m
2 stops
$425Multiple Airlines
Wed, Mar 4 - Tue, Mar 10
Delta Logo
6:15 am - 6:30 pm
ORD
-
KOA
16h 15m
2 stops
Delta Logo
9:55 pm - 1:22 pm
KOA
-
ORD
11h 27m
1 stop
$430Delta
Tue, Feb 24 - Thu, Mar 5
Southwest Logo
8:10 am - 9:20 pm
MDW
-
KOA
17h 10m
2 stops
Southwest Logo
9:25 pm - 12:35 pm
KOA
-
MDW
11h 10m
1 stop
$461Southwest
Mon, Feb 23 - Mon, Mar 2
Southwest Logo
7:55 am - 6:10 pm
MDW
-
KOA
14h 15m
2 stops
Southwest Logo
12:35 pm - 5:55 am
KOA
-
MDW
13h 20m
2 stops
$466Southwest
Thu, Feb 26 - Fri, Mar 6

Southwest flights from Chicago to Kailua-Kona

Our best Southwest deals on Chicago to Kailua-Kona flight tickets
Southwest
Feb 23
MDW8:10 amChicago Midway
17h 10m
2 stops
KOA9:20 pmKona Intl
Mar 2
KOA9:25 pmKona Intl
11h 10m
1 stop
MDW12:35 pmChicago Midway
$461
Southwest
Feb 26
MDW7:55 amChicago Midway
14h 15m
2 stops
KOA6:10 pmKona Intl
Mar 6
KOA12:35 pmKona Intl
13h 20m
2 stops
MDW5:55 amChicago Midway
$466
Southwest
Feb 26
MDW5:00 amChicago Midway
12h 45m
1 stop
KOA1:45 pmKona Intl
Mar 6
KOA12:35 pmKona Intl
13h 20m
2 stops
MDW5:55 amChicago Midway
$487

Delta flights from Chicago to Kailua-Kona

Our best Delta deals on Chicago to Kailua-Kona flight tickets
Delta
Feb 23
ORD7:15 amChicago O'Hare Intl
12h 36m
1 stop
KOA3:51 pmKona Intl
Mar 3
KOA9:55 pmKona Intl
11h 27m
1 stop
ORD1:22 pmChicago O'Hare Intl
$424
Delta
Feb 24
ORD6:15 amChicago O'Hare Intl
16h 15m
2 stops
KOA6:30 pmKona Intl
Mar 5
KOA9:55 pmKona Intl
11h 27m
1 stop
ORD1:22 pmChicago O'Hare Intl
$430
Delta
Feb 24
ORD7:15 amChicago O'Hare Intl
15h 15m
2 stops
KOA6:30 pmKona Intl
Mar 4
KOA10:55 pmKona Intl
14h 47m
2 stops
ORD5:42 pmChicago O'Hare Intl
$435

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 26, 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 3/4

3:07 pm-3:53 pm

1 stop28h 46m

Kona Intl

Tue 3/10

12:10 pm-11:59 pm

1 stop30h 49m

$402

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 3/4

8:20 am-3:53 pm

1 stop35h 33m

Kona Intl

Mon 3/9

1:56 pm-2:58 pm

2 stops20h 02m

$405

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 3/2

8:20 am-10:15 pm

2 stops17h 55m

Kona Intl

Tue 3/10

12:10 pm-2:58 pm

1 stop21h 48m

$408

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sun 3/8

3:07 pm-2:53 pm

1 stop28h 46m

Kona Intl

Thu 3/12

12:10 pm-11:59 pm

1 stop30h 49m

$412

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 2/25

5:00 am-3:30 pm

1 stop14h 30m

Kona Intl

Wed 3/4

10:40 pm-3:05 pm

1 stop12h 25m

$422

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 2/23

7:40 am-7:39 pm

1 stop15h 59m

Kona Intl

Thu 3/5

9:55 pm-1:22 pm

1 stop11h 27m

$424

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 3/4

3:07 pm-3:53 pm

1 stop28h 46m

Kona Intl

Tue 3/10

9:01 pm-2:58 pm

2 stops12h 57m

$425

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 2/24

6:15 am-6:30 pm

2 stops16h 15m

Kona Intl

Thu 3/5

9:55 pm-1:22 pm

1 stop11h 27m

$430

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 2/23

8:10 am-9:20 pm

2 stops17h 10m

Kona Intl

Mon 3/2

9:25 pm-12:35 pm

1 stop11h 10m

$461

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Thu 2/26

7:55 am-6:10 pm

2 stops14h 15m

Kona Intl

Fri 3/6

12:35 pm-5:55 am

2 stops13h 20m

$466

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 $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 $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

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 $343Free CancellationRating
7.9
8,111 reviews
Search Delta flights
Alaska AirlinesPriceFrom $419Free CancellationRating
8.0
11,792 reviews
Search Alaska Airlines flights
Hawaiian AirlinesPriceFrom $429Free CancellationRating
7.8
2,829 reviews
Search Hawaiian Airlines flights
United AirlinesPriceFrom $447Free CancellationRating
7.4
9,199 reviews
Search United Airlines flights
American AirlinesPriceFrom $453Free CancellationRating
7.2
11,189 reviews
Search American Airlines flights
SouthwestPriceFrom $578Free CancellationRating
8.0
4,268 reviews
Search Southwest 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 1 flight/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 $967. 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.

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