Find Cheap Flights from Chicago O'Hare International to Kailua-Kona (ORD - KOA)

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Good to Know

Low Season:
February
Best time to beat the crowds
2%
expected price decrease
High Season:
July
Most popular time to fly
7%
expected price increase
Average Price:
$3663
(avg. price over the last 2 weeks)
Good Deal:
$3663
or less (round trip)

When to Book Flights from Chicago O'Hare International to Kailua-Kona

Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

The cheapest flight from Chicago O'Hare International to Kailua-Kona was found 48 days before departure, on average.
Book at least 1 week before departure in order to get a below-average price.
High season is considered to be June, July and August. The cheapest month to fly is February.
Morning departure is around 6% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Chicago O'Hare International to Kailua-Kona Flights

How long does a flight from Chicago O'Hare International to Kailua-Kona take?
An average nonstop flight takes 14h 10m, covering a distance of 4207 miles.
Which airlines provide the cheapest flights from Chicago O'Hare International to Kailua-Kona?
In the past 3 days, the cheapest round-trip tickets were found on Alaska Airlines ($535), Multiple Airlines ($627) and United ($824).
Do I need a passport to fly between Chicago O'Hare International and Kailua-Kona?
No.

Book cheap flights from Chicago O'Hare International to Kailua-Kona (round-trip)

Airports
Origin
Chicago
$535
only
$535
Destination
Kailua-Kona
$535
only
$535
Mon, Jan 29
ORD
KOA
14h 42m
Tue, Feb 6
KOA
ORD
19h 55m
Trip: 9 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 16524 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
HNL
SAN
Excellent 9.3

The crew was very kind and the in flight entertainment was perfect. I didn't have headphones so I was ready to purchase some, but Alaska gives them out for FREE. The seats were also one of the most comfortable (for coach standards) I've been in.

Not a huge deal but I'm one of those people who are alwayscold and got cold on the flight. Unfortunately they don't have blankets but I had a hoodie that flight attend got down for me that worked just fine. Also, no complimentary food, so just make sure to stock up before boarding.

DFW
PDX
Excellent 9.0

Everything

N/A

SJC
SEA
Excellent 9.5

Being on time.

LAX
SEA
Excellent 10.0

crew was nice Slept easily

EWR
SJC
Excellent 10.0

Price of the tickets, boarding, entertainment options, food options for purchase and best of all on time (before time) arrival.

Thu, Apr 26
ORD
KOA
14h 19m
Mon, Apr 30
KOA
ORD
17h 01m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Jul 19
ORD
KOA
20h 56m
Wed, Jul 25
KOA
ORD
12h 39m
Trip: 7 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 53951 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
IAD
MUC
Excellent 9.3

Good experience, no issues.

Good overall.

BRU
IAD
Good 7.0

Good food, entertainment options, communication from pilot

none of the flight attendants seemed to be friendly- literally all of them were neutral or slightly rude at best. Not impressed.

SEA
SFO
Excellent 9.3

Nothing great, nothing bad. took off and landed on time.

paced seats, nit enough room for carry ons.

IND
EWR
Good 7.3

Crew was outstanding . Boarding was easy. Ahead of schedule arrival

Return to terminal required a bus and then off loading like cattle for sale. Came in through maintenance area. One hour from landing to baggage claim. Terrible!

EWR
EDI
Mediocre 2.0

United staff worked with me to book a round-about itinerary on a different airline that got me to my destination within 8 hours of the original flight. Progress announcements were made at regular, predictable intervals.

My flight was cancelled an hour after scheduled takeoff due to mechanical issues. The plane was actually repaired, but the time it took to do so exceeded the flight crew's hours. I understand the practical implications, but in the moment it did feel maddeningly bureaucratic.

Mon, Jul 2
ORD
KOA
18h 28m
Wed, Jul 18
KOA
ORD
12h 38m
Trip: 17 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15421 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
CUN
Okay 4.0

The flight was delayed for 4 hours.

DTW
PVR
Excellent 8.6

Easy flight from check-in to boarding to deplaning.

Nothing really! No entertainment and nothing but almonds eaten.

MSP
CUN
Good 6.3

On time, pretty friendly crew

Too small a plane for that long a trip. Bathrooms were VERY small & rare.

SJD
ATL
Good 7.6

Our Delta plane was brand spanking new. Everything worked and the inflight entertainment system was fantastic with many movies to choose from, free headphones, games, tv shows, etc. The crew was polite and the seating at least as comfortable as expected for a 4 hour flight.

The restrooms in the rear of the plane were remarkably small, even by airline standards. I'm a somewhat larger person and I fit, but I know a lot of people who would literally not be able to fit on the toilet without touching both of the sidewalls or risk getting stuck in there. The boarding process at San Jose Del Cabo was the most ridiculous setup I've ever experienced. There were numerous flights boarding out of the same gates and at least 3 or 4 lines for different destinations forming on a ramp just outside the gates. There were guys with signs trying to herd people into the correct lines and then loading the people onto buses which took you out to the planes. The planes were loading from both the front and rear doors and people were getting tangled up inside because of the haphazard loading process. Very easy for a person to end up on an incorrect plane!!

MSP
SMF
Good 6.3

For a 3 hour flight no onboard entertainment. Such a let down

Wed, Jun 20
ORD
KOA
15h 09m
Wed, Jun 27
KOA
ORD
12h 23m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27489 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
SAN
PHX
Excellent 9.0

The friendly and attentive flight staff.

MIA
SJU
Good 6.0

Last minute cancellation and reschedule if original flight with 20 people hounding the gate for standby status. Craziness. These last minute revisions mist stop

DFW
DCA
Excellent 10.0

Fast and efficient service

Not applicable

CLT
LHR
Excellent 8.0

The low price! It was on American Airlines which the same flight was more expensive. Professional flight attendants

Cramped seating but can't really complain because of the price

MIA
LHR
Excellent 8.0

No being able to book seats easily and having to phone in for this

Thu, Feb 8
ORD
KOA
21h 41m
Tue, Feb 13
KOA
ORD
22h 46m
Trip: 6 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 16524 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
SAT
SEA
Mediocre 2.0

The cabin crew were very nice.

The original flight was cancelled due to weather condition that caused a domino effect for me that disrupted all my other travel plans.

SEA
ANC
Excellent 10.0

served some great refreshments even while serving was going on they made it easy to sleep

ANC
FAI
Excellent 10.0

great views! pilot interactions one woman on the crew was extremely personable & friendly!!! she stood out above the rest. :) (don't know her name but short blonde hair. friend and I agreed that she was great) windows clean enough to take some great pictures from the window

HNL
SAN
Excellent 9.3

The crew was very kind and the in flight entertainment was perfect. I didn't have headphones so I was ready to purchase some, but Alaska gives them out for FREE. The seats were also one of the most comfortable (for coach standards) I've been in.

Not a huge deal but I'm one of those people who are alwayscold and got cold on the flight. Unfortunately they don't have blankets but I had a hoodie that flight attend got down for me that worked just fine. Also, no complimentary food, so just make sure to stock up before boarding.

SEA
ANC
Excellent 10.0

Everything

N/A

Tue, May 8
ORD
KOA
14h 10m
Tue, May 15
KOA
ORD
16h 29m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Apr 17
ORD
KOA
18h 09m
Mon, Apr 23
KOA
ORD
20h 22m
Trip: 7 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 16524 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
HNL
SAN
Excellent 9.3

The crew was very kind and the in flight entertainment was perfect. I didn't have headphones so I was ready to purchase some, but Alaska gives them out for FREE. The seats were also one of the most comfortable (for coach standards) I've been in.

Not a huge deal but I'm one of those people who are alwayscold and got cold on the flight. Unfortunately they don't have blankets but I had a hoodie that flight attend got down for me that worked just fine. Also, no complimentary food, so just make sure to stock up before boarding.

SFO
PDX
Excellent 8.0

smooth quiet good leg room

fat man to my left

SEA
ANC
Excellent 10.0

Everything

N/A

SJC
SEA
Excellent 9.5

Being on time.

DFW
PDX
Excellent 9.0

Everything

N/A

Wed, May 16
ORD
KOA
17h 19m
Tue, May 22
KOA
ORD
12h 38m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Feb 6
ORD
KOA
18h 23m
Sun, Feb 11
KOA
ORD
19h 55m
Trip: 6 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 16524 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
SEA
ANC
Excellent 10.0

It was great we had a nice Tailwind that got us in 50 min early . Space in seating was more than adequit.

Their wasn't anything I disliked.

DFW
PDX
Excellent 9.0

Everything

N/A

HNL
SJC
Excellent 8.0

Seemed roomy, crew was nice.

SAT
SEA
Mediocre 2.0

The cabin crew were very nice.

The original flight was cancelled due to weather condition that caused a domino effect for me that disrupted all my other travel plans.

SEA
ANC
Excellent 10.0

Everything

N/A

Thu, Mar 1
ORD
KOA
21h 41m
Mon, Mar 5
KOA
ORD
32h 41m
Trip: 5 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 16524 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
SEA
ANC
Excellent 10.0

It was great we had a nice Tailwind that got us in 50 min early . Space in seating was more than adequit.

Their wasn't anything I disliked.

HNL
SAN
Excellent 9.3

The crew was very kind and the in flight entertainment was perfect. I didn't have headphones so I was ready to purchase some, but Alaska gives them out for FREE. The seats were also one of the most comfortable (for coach standards) I've been in.

Not a huge deal but I'm one of those people who are alwayscold and got cold on the flight. Unfortunately they don't have blankets but I had a hoodie that flight attend got down for me that worked just fine. Also, no complimentary food, so just make sure to stock up before boarding.

SEA
ANC
Excellent 10.0

served some great refreshments even while serving was going on they made it easy to sleep

SFO
PDX
Excellent 8.0

smooth quiet good leg room

fat man to my left

EWR
SJC
Excellent 10.0

Price of the tickets, boarding, entertainment options, food options for purchase and best of all on time (before time) arrival.

Tue, Jun 5
ORD
KOA
28h 55m
Mon, Jun 11
KOA
ORD
18h 33m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Mar 1
ORD
KOA
21h 41m
Sat, Mar 10
KOA
ORD
36h 33m
Trip: 10 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 16524 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
SEA
ANC
Excellent 10.0

It was great we had a nice Tailwind that got us in 50 min early . Space in seating was more than adequit.

Their wasn't anything I disliked.

SFO
PDX
Excellent 8.0

smooth quiet good leg room

fat man to my left

HNL
SJC
Excellent 8.0

Seemed roomy, crew was nice.

SJC
SEA
Excellent 9.5

Being on time.

LAX
SEA
Excellent 10.0

crew was nice Slept easily

Sun, Jun 3
ORD
KOA
25h 15m
Mon, Jun 11
KOA
ORD
18h 33m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Mar 12
ORD
KOA
23h 59m
Mon, Mar 19
KOA
ORD
22h 01m
Trip: 8 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 16524 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
LAX
SEA
Excellent 10.0

crew was nice Slept easily

HNL
SJC
Excellent 8.0

Seemed roomy, crew was nice.

SAT
SEA
Mediocre 2.0

The cabin crew were very nice.

The original flight was cancelled due to weather condition that caused a domino effect for me that disrupted all my other travel plans.

SJC
SEA
Excellent 9.5

Being on time.

DFW
PDX
Excellent 9.0

Everything

N/A

Fri, Jan 26
ORD
KOA
25h 29m
Sat, Feb 3
KOA
ORD
19h 55m
Trip: 9 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 16524 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
SEA
ANC
Excellent 10.0

It was great we had a nice Tailwind that got us in 50 min early . Space in seating was more than adequit.

Their wasn't anything I disliked.

SJC
SEA
Excellent 9.5

Being on time.

SEA
ANC
Excellent 10.0

Everything

N/A

HNL
SAN
Excellent 9.3

The crew was very kind and the in flight entertainment was perfect. I didn't have headphones so I was ready to purchase some, but Alaska gives them out for FREE. The seats were also one of the most comfortable (for coach standards) I've been in.

Not a huge deal but I'm one of those people who are alwayscold and got cold on the flight. Unfortunately they don't have blankets but I had a hoodie that flight attend got down for me that worked just fine. Also, no complimentary food, so just make sure to stock up before boarding.

SEA
ANC
Excellent 10.0

served some great refreshments even while serving was going on they made it easy to sleep

Tue, Mar 20
ORD
KOA
23h 59m
Tue, Apr 3
KOA
ORD
22h 01m
Trip: 15 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 16524 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
HNL
SJC
Excellent 8.0

Seemed roomy, crew was nice.

DFW
PDX
Excellent 9.0

Everything

N/A

SFO
PDX
Excellent 8.0

smooth quiet good leg room

fat man to my left

SEA
ANC
Excellent 10.0

Everything

N/A

SAT
SEA
Mediocre 2.0

The cabin crew were very nice.

The original flight was cancelled due to weather condition that caused a domino effect for me that disrupted all my other travel plans.

Fri, Mar 30
ORD
KOA
15h 17m
Sat, Apr 7
KOA
ORD
19h 31m
$1444
Trip: 9 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 16524 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
LAX
SEA
Excellent 10.0

crew was nice Slept easily

SEA
ANC
Excellent 10.0

served some great refreshments even while serving was going on they made it easy to sleep

HNL
SJC
Excellent 8.0

Seemed roomy, crew was nice.

SEA
ANC
Excellent 10.0

Everything

N/A

HNL
SAN
Excellent 9.3

The crew was very kind and the in flight entertainment was perfect. I didn't have headphones so I was ready to purchase some, but Alaska gives them out for FREE. The seats were also one of the most comfortable (for coach standards) I've been in.

Not a huge deal but I'm one of those people who are alwayscold and got cold on the flight. Unfortunately they don't have blankets but I had a hoodie that flight attend got down for me that worked just fine. Also, no complimentary food, so just make sure to stock up before boarding.

Show more results

Chicago O'Hare International to Kailua-Kona Flight Information

Flights Arrive in Kailua-Kona
Flights Depart from Chicago O'Hare International
Flight Price $535
Distance 4207 miles
Airlines Alaska Airlines, United, Delta, American Airlines
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

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We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.