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Cheap flights from Chicago to Kailua-Kona from $205

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 11/16. 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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Find the cheapest flights from Chicago to Kailua-Kona

Cheap round-trip flights

Delta Logo
7:37 am - 5:30 pmORD-KOA
14h 53m1 stop
Delta Logo
9:30 pm - 5:10 pmKOA-ORD
14h 40m1 stop
$382Delta
Find Deal
Wed, Oct 22 - Mon, Oct 27
Delta Logo
7:37 am - 7:23 pmORD-KOA
16h 46m2 stops
Delta Logo
9:30 pm - 1:30 pmKOA-ORD
11h 00m1 stop
$387Delta
Find Deal
Wed, Oct 8 - Wed, Oct 22
United Airlines Logo
6:15 am - 11:56 amORD-KOA
10h 41m1 stop
United Airlines Logo
1:05 pm - 9:36 amKOA-ORD
15h 31m2 stops
$452United Airlines
Find Deal
Wed, Oct 15 - Mon, Oct 20
Alaska Airlines Logo
10:00 am - 9:40 pmORD-KOA
15h 40m2 stops
Alaska Airlines Logo
9:00 pm - 4:30 pmKOA-ORD
15h 30m2 stops
$458Alaska Airlines
Find Deal
Wed, Nov 12 - Mon, Nov 17
Alaska Airlines Logo
2:54 pm - 1:43 pmORD-KOA
27h 49m1 stop
Alaska Airlines Logo
11:09 am - 1:54 pmKOA-ORD
21h 45m1 stop
$462Alaska Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
American Airlines Logo
7:00 am - 1:58 pmORD-KOA
11h 58m1 stop
American Airlines Logo
9:45 pm - 3:59 pmKOA-ORD
13h 14m1 stop
$463American Airlines
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Mon, Oct 27 - Fri, Oct 31
United Airlines Logo
7:10 am - 3:18 pmORD-KOA
13h 08m1 stop
United Airlines Logo
8:55 pm - 1:15 pmKOA-ORD
12h 20m1 stop
$477United Airlines
Find Deal
Fri, Oct 31 - Mon, Nov 10
American Airlines Logo
5:00 am - 1:58 pmORD-KOA
13h 58m2 stops
American Airlines Logo
9:35 pm - 11:53 amKOA-ORD
10h 18m1 stop
$482American Airlines
Find Deal
Fri, Oct 31 - Wed, Nov 12
Southwest Logo
6:05 am - 1:00 pmMDW-KOA
11h 55m1 stop
Southwest Logo
8:30 pm - 3:10 pmKOA-MDW
13h 40m1 stop
$485Southwest
Find Deal
Wed, Oct 22 - Mon, Oct 27
Southwest Logo
6:05 am - 1:00 pmMDW-KOA
11h 55m1 stop
Southwest Logo
8:30 pm - 1:35 pmKOA-MDW
12h 05m2 stops
$490Southwest
Find Deal
Wed, Oct 22 - Mon, Oct 27

Alaska Airlines flights from Chicago to Kailua-Kona

Our best Alaska Airlines deals on Chicago to Kailua-Kona flight tickets
Alaska Airlines
Nov 12
ORD10:00 amChicago O'Hare Intl
15h 40m
2 stops
KOA9:40 pmKona Intl
Nov 17
KOA9:00 pmKona Intl
15h 30m
2 stops
ORD4:30 pmChicago O'Hare Intl
$458
Find similar
Alaska Airlines
Oct 27
ORD2:54 pmChicago O'Hare Intl
27h 49m
1 stop
KOA1:43 pmKona Intl
Oct 31
KOA11:09 amKona Intl
21h 45m
1 stop
ORD1:54 pmChicago O'Hare Intl
$462
Find similar
Alaska Airlines
Oct 27
ORD2:54 pmChicago O'Hare Intl
27h 49m
1 stop
KOA1:43 pmKona Intl
Oct 31
KOA6:00 amKona Intl
13h 24m
2 stops
ORD12:24 amChicago O'Hare Intl
$468
Find similar

American Airlines flights from Chicago to Kailua-Kona

Our best American Airlines deals on Chicago to Kailua-Kona flight tickets
American Airlines
Oct 27
ORD7:00 amChicago O'Hare Intl
11h 58m
1 stop
KOA1:58 pmKona Intl
Oct 31
KOA9:45 pmKona Intl
13h 14m
1 stop
ORD3:59 pmChicago O'Hare Intl
$463
Find similar
American Airlines
Oct 31
ORD5:00 amChicago O'Hare Intl
13h 58m
2 stops
KOA1:58 pmKona Intl
Nov 12
KOA9:35 pmKona Intl
10h 18m
1 stop
ORD11:53 amChicago O'Hare Intl
$482
Find similar
American Airlines
Oct 8
ORD6:03 amChicago O'Hare Intl
12h 55m
1 stop
KOA1:58 pmKona Intl
Oct 22
KOA9:45 pmKona Intl
13h 14m
1 stop
ORD3:59 pmChicago O'Hare Intl
$516
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 September 17, 2025.
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 10/22

7:37 am-5:30 pm

1 stop14h 53m

Kona Intl

Mon 10/27

9:30 pm-5:10 pm

1 stop14h 40m

$382

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 10/8

7:37 am-7:23 pm

2 stops16h 46m

Kona Intl

Wed 10/22

9:30 pm-1:30 pm

1 stop11h 00m

$387

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 10/15

6:15 am-11:56 am

1 stop10h 41m

Kona Intl

Mon 10/20

1:05 pm-9:36 am

2 stops15h 31m

$452

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 11/12

10:00 am-9:40 pm

2 stops15h 40m

Kona Intl

Mon 11/17

9:00 pm-4:30 pm

2 stops15h 30m

$458

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 10/27

2:54 pm-1:43 pm

1 stop27h 49m

Kona Intl

Fri 10/31

11:09 am-1:54 pm

1 stop21h 45m

$462

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 10/27

7:00 am-1:58 pm

1 stop11h 58m

Kona Intl

Fri 10/31

9:45 pm-3:59 pm

1 stop13h 14m

$463

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 10/31

7:10 am-3:18 pm

1 stop13h 08m

Kona Intl

Mon 11/10

8:55 pm-1:15 pm

1 stop12h 20m

$477

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Fri 10/31

5:00 am-1:58 pm

2 stops13h 58m

Kona Intl

Wed 11/12

9:35 pm-11:53 am

1 stop10h 18m

$482

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 10/22

6:05 am-1:00 pm

1 stop11h 55m

Kona Intl

Mon 10/27

8:30 pm-3:10 pm

1 stop13h 40m

$485

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Wed 10/22

6:05 am-1:00 pm

1 stop11h 55m

Kona Intl

Mon 10/27

8:30 pm-1:35 pm

2 stops12h 05m

$490

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 $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 $592.

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 $1,376.

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 $703 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 $573 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 20% 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 September 2025, prices for Chicago to Kailua-Kona flights are approximately 23% 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

$1,163

Fastest flight time

9h 10m

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 $1,163
The fastest flight from Chicago to Kailua-Kona takes 9h 10m
Direct flights go from Chicago to Kailua-Kona on Sunday. There are no airlines offering direct flights.
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 10h 41m.

  • 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 $421Free CancellationRating
7.9
7,961 reviews
Search Delta flights
Alaska AirlinesPriceFrom $423Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $429Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $451Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
Hawaiian AirlinesPriceFrom $484Free CancellationRating
7.8
2,729 reviews
Search Hawaiian Airlines flights
SouthwestPriceFrom $593Free CancellationRating
8.0
4,242 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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