Find Cheap Flights from Chicago to Kailua-Kona (CHI - KOA)

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Good to Know

Low Season:
January
Best time to beat the crowds
3%
expected price decrease
High Season:
December
Most popular time to fly
1%
expected price increase
Average Price:
$928
(avg. price over the last 2 weeks)
Good Deal:
$777
or less (round trip)

When to Book Flights from Chicago to Kailua-Kona

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

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $776 or less.
The cheapest flight from Chicago to Kailua-Kona was found 1 day before departure, on average.
Book at least 1 week before departure in order to get a below-average price.
Morning departure is around 4% 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 to Kailua-Kona Flights

How long does a flight from Chicago to Kailua-Kona take?
An average nonstop flight takes 12h 23m, covering a distance of 4222 miles.
Which airlines provide the cheapest flights from Chicago to Kailua-Kona?
In the past 3 days, the cheapest round-trip tickets were found on Alaska Airlines ($505), Multiple Airlines ($617) and Delta ($701).
Do I need a passport to fly between Chicago and Kailua-Kona?
No.

Book cheap flights from Chicago to Kailua-Kona (round-trip)

Airports
Origin
Chicago
$505
only
$505
$701
only
$701
Destination
Kailua-Kona
$505
only
$505
Tue, Apr 17
ORD
KOA
18h 09m
Wed, Apr 25
KOA
ORD
27h 22m
Trip: 9 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 17011 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
SJC
SJD
Okay 4.6

poor

SEA
DEN
Excellent 10.0

boarding was late due to repairs on the plane

LAX
MEX
Mediocre 2.0

My luggage didn’t come on my flight. I was given a phone number to call for updates. I didn’t receive my bag until the following day. It was very unprofessional.

ORD
SEA
Excellent 9.6

crew's upbeat attitude

very limited drink choices

FAI
SEA
Excellent 9.6

Easy on off and let us sleep

Mon, Mar 12
ORD
KOA
23h 38m
Mon, Mar 19
KOA
ORD
34h 59m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Apr 16
MDW
KOA
15h 44m
Tue, Apr 24
KOA
MDW
15h 14m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

JFK
CDG
Excellent 10.0

The food and the service

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

Tue, May 1
ORD
KOA
20h 09m
Thu, May 3
KOA
ORD
20h 22m
Trip: 3 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 17011 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
SEA
DEN
Excellent 10.0

i wish Alaska would fly straight to Denver from Montana. I fly from Montana to Denver a lot and it ends up being a whole day of travel instead of a couple hour flight.

SJC
SJD
Okay 4.6

poor

RDU
SEA
Excellent 8.3

The flight crew was incredibly sweet and helpful; one of them even gave me their personal TUMS when I said I didn't feel well.

The flight boarded 30 minutes early; I arrived to my gate at the time of when my ticket said boarding started, but they were already calling final boarding call for my flight. I completely panicked. The plane was clean but the seats are very close together and there were no complimentary snacks- even though it was a 6 hour flight. On my flight back from Seattle on Delta, we got a complimentary meal AND a complimentary snack. I was expecting my Alaskan flight to be better based on everything I'd heard from friends, but my return Delta flight showed Alaska up; it was a spacier plane with way more food offered.

LAX
MEX
Mediocre 2.0

My luggage didn’t come on my flight. I was given a phone number to call for updates. I didn’t receive my bag until the following day. It was very unprofessional.

PDX
SFO
Okay 4.3

The crew was funny and handled the delay nicely

No notice of 2 hour delay

Fri, Jul 20
ORD
KOA
15h 09m
Sat, Jul 28
KOA
ORD
10h 59m
$1080
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28416 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
LAX
MIA
Mediocre 2.0

Couldn’t sleep because the AC wasnt working. Most miserable flight my life

The AC wasn’t working it was the most miserable flight ever

DFW
SAT
Okay 4.0

It was short

Completely full plane. Ridiculously tight seat pitch. Overhead bins full. 45-minute delay for a dead-heading flight crew. Long wait for checked baggage. No beverage service because of turbulence. Flight crew out of position is a management problem, don't make it an inconvenience for a 737 full of paying passengers!

DEN
ORD
Good 6.4

I'm not sure where the problem was - whether with AA or Royal Jordanian, but my luggage did not make it to Amman with me. In fact, there was a whole group of passengers traveling on American from different US cities, switching to RJ in Chicago, whose luggage did not come on the flight to Amman. My advice: be sure to pack enough for a couple of days in your carryon - and don't accept an offer to check your carryon to its final destination!

JFK
MAD
Okay 4.0

Very old plane. No personal entertainment. Very basic service.

LAX
CLT
Mediocre 2.6

I got there safely.

I will never fly American Airlines again. From the moment I checked in with the ticket agent to getting off the plane it was a disaster. The ticket agent was rude, hostile, and dismissive. Employees walked through the line at security forcing everyone to consolidate their belongings to one bag. I had a large wallet in my hand and was told I had to step out of line to put it in my backpack. They only allow you one bag to carry on without paying extra. At the time of boarding they announced that the overhead storage was full so even those that paid extra were still forced to check their bags. The plane was dirty, the service was slow, overall just gross. They don’t have WiFi or in flight entertainment so I paid the $20 to purchase the WiFi. It was worthless. I couldn’t stream anything, even music kept stopping to buffer. I understand it will be slower then on ground WiFi, but it was impossible to watch anything and a complete waste of money.

Sat, Apr 21
ORD
KOA
38h 24m
Tue, May 1
KOA
ORD
30h 17m
Trip: 11 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 17011 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
SEA
LIH
Excellent 10.0

Flt arrived early. The crew were all very friendly and the service was excellent.

SEA
MCO
Mediocre 2.3

I dispatched a guitar in a hard case. It was labeled fragile and sent to a separate compartment. The guitar was poorly treated and the case was broken all over. Very disappointing. On top of that I had requested window seat and got the middle seat. No food was served and there was no movies to watch or anything, considering this was a five hour flight

LAX
MEX
Mediocre 2.0

My luggage didn’t come on my flight. I was given a phone number to call for updates. I didn’t receive my bag until the following day. It was very unprofessional.

SEA
SNA
Excellent 9.3

Up and down, no problems

Chocolate and almonds for breakfast snack?

SEA
DEN
Excellent 10.0

i wish Alaska would fly straight to Denver from Montana. I fly from Montana to Denver a lot and it ends up being a whole day of travel instead of a couple hour flight.

Tue, Mar 6
ORD
KOA
12h 23m
Mon, Mar 12
KOA
ORD
23h 23m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Tue, May 1
MDW
KOA
13h 58m
Thu, May 3
KOA
MDW
14h 26m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

Sat, Aug 11
ORD
KOA
21h 45m
Mon, Aug 20
KOA
ORD
20h 35m
Trip: 10 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 17011 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
SEA
LIH
Excellent 10.0

Flt arrived early. The crew were all very friendly and the service was excellent.

SEA
SJC
Okay 4.6

Flight time

Behavior of Stewardess Barbara extremely rude. I had gone to the restroom at the back of the aircraft at the beginning of service. I went up and wanted to sit on my 7C seat but she refused to move the cart to accommodate me to pass and made me stand at the back of the flight for 2 hour of the 1 hr 45 mins flight time

PDX
SFO
Okay 4.3

The crew was funny and handled the delay nicely

No notice of 2 hour delay

SEA
DEN
Excellent 10.0

i wish Alaska would fly straight to Denver from Montana. I fly from Montana to Denver a lot and it ends up being a whole day of travel instead of a couple hour flight.

SEA
DEN
Excellent 10.0

boarding was late due to repairs on the plane

Sun, May 27
ORD
KOA
19h 45m
Mon, Jun 4
KOA
ORD
12h 38m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Mar 12
MDW
KOA
14h 48m
Mon, Mar 19
KOA
MDW
14h 34m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

SLC
YYZ
Excellent 9.6

Z

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

Wed, Feb 28
ORD
KOA
12h 43m
Tue, Apr 3
KOA
ORD
16h 02m
Trip: 34 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Mar 8
MDW
KOA
15h 48m
Tue, Mar 13
KOA
MDW
14h 34m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

SLC
YYZ
Excellent 9.6

Z

JFK
CDG
Excellent 10.0

The food and the service

Mon, Jun 4
ORD
KOA
29h 42m
Wed, Jun 13
KOA
ORD
12h 42m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

SLC
YYZ
Excellent 9.6

Z

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

Sat, Jun 9
ORD
KOA
32h 30m
Sat, Jun 16
KOA
ORD
27h 30m
Trip: 8 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 17011 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
SEA
SJC
Okay 4.6

Flight time

Behavior of Stewardess Barbara extremely rude. I had gone to the restroom at the back of the aircraft at the beginning of service. I went up and wanted to sit on my 7C seat but she refused to move the cart to accommodate me to pass and made me stand at the back of the flight for 2 hour of the 1 hr 45 mins flight time

SEA
SNA
Excellent 9.3

Up and down, no problems

Chocolate and almonds for breakfast snack?

PDX
SFO
Okay 4.3

The crew was funny and handled the delay nicely

No notice of 2 hour delay

SEA
DEN
Excellent 10.0

i wish Alaska would fly straight to Denver from Montana. I fly from Montana to Denver a lot and it ends up being a whole day of travel instead of a couple hour flight.

LAX
MEX
Mediocre 2.0

My luggage didn’t come on my flight. I was given a phone number to call for updates. I didn’t receive my bag until the following day. It was very unprofessional.

Sun, Jun 3
ORD
KOA
13h 55m
Sat, Jun 9
KOA
ORD
27h 30m
Trip: 7 days
8.4ExcellentShow reviews
Overall 8.4 Excellent
Based on 17011 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
SEA
DEN
Excellent 10.0

i wish Alaska would fly straight to Denver from Montana. I fly from Montana to Denver a lot and it ends up being a whole day of travel instead of a couple hour flight.

ORD
SEA
Excellent 9.6

crew's upbeat attitude

very limited drink choices

SEA
SNA
Excellent 9.3

Up and down, no problems

Chocolate and almonds for breakfast snack?

SEA
MCO
Mediocre 2.3

I dispatched a guitar in a hard case. It was labeled fragile and sent to a separate compartment. The guitar was poorly treated and the case was broken all over. Very disappointing. On top of that I had requested window seat and got the middle seat. No food was served and there was no movies to watch or anything, considering this was a five hour flight

FAI
SEA
Excellent 9.6

Easy on off and let us sleep

Wed, Jul 4
ORD
KOA
18h 26m
Thu, Jul 12
KOA
ORD
12h 42m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

Wed, Jun 6
MDW
KOA
13h 58m
Mon, Jun 18
KOA
MDW
12h 23m
Trip: 13 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

Tue, Jul 3
MDW
KOA
15h 28m
Tue, Jul 17
KOA
MDW
14h 36m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

JFK
CDG
Excellent 10.0

The food and the service

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

Wed, May 23
MDW
KOA
15h 30m
Sat, Jun 2
KOA
MDW
15h 33m
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SLC
YYZ
Excellent 9.6

Z

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

Show more results

Chicago to Kailua-Kona Flight Information

Flights Arrive in Kailua-Kona
Flights Depart from Chicago
Flight Price $505
Distance 4222 miles
Airlines Alaska Airlines, Delta, American Airlines
*
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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.