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CHI - KOA

$211 Find cheap flights from Chicago to Kailua-Kona

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Kailua-Kona departing on 5/31. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
lun. 6/3
lun. 6/10

Search hundreds of travel sites at once for deals on flights to Kailua-Kona

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Kailua-Kona, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Kailua-Kona, as well as popular online travel agencies
In the last 7 days travelers have searched 43,369,418 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Chicago to Kailua-Kona (CHI-KOA)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Kailua-Kona that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:00 am - 9:00 pmORD-KOA
20h 00m1 stop
12:29 pm - 5:15 amKOA-ORD
11h 46m1 stop
$417Undisclosed Carrier
Find Deal
jeu., août 15 - lun., août 19
6:00 am - 9:00 pmORD-KOA
20h 00m1 stop
12:29 pm - 5:15 amKOA-ORD
11h 46m1 stop
$422Alaska Airlines
Find Deal
jeu., août 15 - lun., août 19
7:30 am - 5:14 pmORD-KOA
14h 44m1 stop
9:45 pm - 9:11 pmKOA-ORD
18h 26m2 stops
$467Delta
Find Deal
sam., août 24 - sam., août 31
6:00 am - 2:11 pmORD-KOA
13h 11m1 stop
1:35 pm - 6:00 amKOA-ORD
11h 25m1 stop
$469American Airlines
Find Deal
mer., sept. 18 - mer., sept. 25
7:30 am - 5:14 pmORD-KOA
14h 44m1 stop
8:45 pm - 5:59 pmKOA-ORD
16h 14m2 stops
$507Delta
Find Deal
jeu., août 15 - lun., août 19
6:00 am - 12:52 pmORD-KOA
11h 52m1 stop
10:30 pm - 3:48 pmKOA-ORD
12h 18m1 stop
$512American Airlines
Find Deal
mar., sept. 3 - lun., sept. 9
8:00 pm - 3:47 pmORD-KOA
24h 47m2 stops
3:30 pm - 12:12 pmKOA-ORD
15h 42m1 stop
sam., mai 25 - mar., mai 28
7:10 am - 3:34 pmORD-KOA
13h 24m1 stop
7:35 pm - 11:35 amKOA-ORD
11h 00m1 stop
$541United Airlines
Find Deal
dim., mai 19 - lun., mai 27
8:00 pm - 3:47 pmORD-KOA
24h 47m2 stops
3:30 pm - 6:23 pmKOA-ORD
21h 53m2 stops
sam., mai 25 - mar., mai 28
1:10 pm - 9:22 pmORD-KOA
13h 12m1 stop
7:35 pm - 11:35 amKOA-ORD
11h 00m1 stop
$551United Airlines
Find Deal
mer., mai 29 - mer., juin 12

Flights from Chicago to Kailua-Kona - Travel Insights & Trends

Get data-powered insights and trends into flights from Chicago to Kailua-Kona to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Kailua-Kona flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Chicago to Kailua-Kona.
Our data shows that the cheapest route for a one-way flight from Chicago to Kailua-Kona cost $583 and was between Chicago O'Hare Intl Airport and Kailua-Kona. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $1,893.

What’s the cheapest day of the week to fly from Chicago to Kailua-Kona?

The average price of all flights from Chicago to Kailua-Kona clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Kailua-Kona on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Chicago to Kailua-Kona. For your return ticket, we recommend flying on a Monday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Chicago to Kailua-Kona?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago to Kailua-Kona, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago to Kailua-Kona is February, where tickets cost $584 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $874 and $845 respectively.

How far in advance should I book a flight from Chicago to Kailua-Kona?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago to Kailua-Kona, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago to Kailua-Kona, you should book around 1 day before departure. For the absolute cheapest price, our data suggests you should book 81 days before departure.

Which airlines provide the cheapest flights from Chicago to Kailua-Kona?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the past 3 days, the cheapest one-way tickets to Kailua-Kona from Chicago were found on Alaska Airlines ($211) and Delta ($250), and the lowest round-trip tickets were found on Alaska Airlines ($422) and Delta ($467).

Which cabin class options are there for flights between Chicago and Kailua-Kona?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 2 cabin class options for the route. These are First and Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Good to know

Low season

May

High season

July

Cheapest flight

$211
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Chicago O'Hare Airport to Kailua-Kona

When to book flights from Chicago to Kailua-Kona

Are your dates flexible? Find out the best times to travel from Chicago to Kailua-Kona based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Kailua-Kona

  • Consider flying First Class when traveling with American Airlines from Chicago to Kailua-Kona. The airline's First Class ticket comes with priority privileges like speed through security, check-in and boarding at the airports, and priority bag handling after your flight. You also get to enjoy comfy seats, premium dining, and free in-flight entertainment.

    What are the common stopover options for flights from Chicago to Kailua Kona?

  • Flights from Chicago to Kailua Kona are generally connecting flights, as there are no direct flights at the moment. These flights have layovers in different cities depending on the airline. Most airlines flying from Chicago to Kailua-Kona have layovers in Seattle, Tacoma (SEA), Los Angeles (LAX), San Francisco (SFO), Atlanta (ATL), Honolulu (HNL), and Denver (DEN).

    Which airlines flying from Chicago to Kailua-Kona assist passengers with special needs?

  • Each airline flying from Chicago to Kailua-Kona offer assistance services for passengers with special needs. Every airline on this route runs a wheelchair assistance program to help travelers with reduced mobility easily get through the airport. If you need a wheelchair for your travel, we recommend informing your airline at least 48 hours before your flight to ensure it is available. These airlines also have attendants who assist passengers with special needs when boarding, moving to and from seats, or disembarking from planes.

    How can I get from the Kailua International Airport to Downtown Kailua-Kona?

  • There are several transportation options from Kona Airport to Kailua-Kona. Buses offer one of the most affordable and convenient ways of completing the trip from the airport to Kailua-Kona. Bus Line 202 runs from the airport to Luhia Street. The buses are operated by Hele-On Bus and depart the airport every 30 minutes. Alternatively, you can taxi or drive from the airport to Kailua-Kona.

    Which airlines flying from Chicago to Kailua-Kona offer better pet policies?

  • What is the cheapest flight from Chicago to Kailua-Kona?

    In the last 3 days, the lowest price for a flight from Chicago to Kailua-Kona was $211 for a one-way ticket and $417 for a round-trip.

  • Do I need a passport to fly between Chicago and Kailua-Kona?

    A passport is not required to fly from Chicago to Kailua-Kona.

  • Which airports will I be using when flying from Chicago to Kailua-Kona?

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at Kona Intl.

  • Which aircraft models fly most regularly from Chicago to Kailua-Kona?

    The Boeing 787-8 Dreamliner is the aircraft model that flies most regularly on the Chicago to Kailua-Kona flight route.

  • Which airline alliances offer flights from Chicago to Kailua-Kona?

    oneworld, SkyTeam, and Star Alliance are the airline alliances operating flights between Chicago and Kailua-Kona, with oneworld being the most commonly used for this route.

  • What is the most popular layover when flying to Kailua-Kona from Chicago?

    Los Angeles is the most popular layover city among KAYAK users traveling from Chicago to Kailua-Kona.

  • Which is the best airline for flights from Chicago to Kailua-Kona, Alaska Airlines or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Kailua-Kona are Alaska Airlines and Delta. With an average price for the route of $714 and an overall rating of 8.0, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $660 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Chicago to Kailua-Kona?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Kailua-Kona.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Kailua-Kona?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kailua-Kona from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Kailua-Kona?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Kailua-Kona with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Kailua-Kona?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Kailua-Kona from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from Chicago to Kailua-Kona

  • Looking for a cheap flight? 25% of our users found flights on this route for $1,976 or less round-trip.
  • If you have a carry-on bag, consider flying with American Airlines on the NYC to BGR route. The airline allows you to board with one standard carry-on bag, which should have 40 lb at most of the weight. Its maximum dimensions must not exceed 22 x 14 x 9 inches. Also, you can have a personal item with sizes 18 x 14 x 8 inches, which must fit under the seat.
  • Flights from Chicago to Kailua-Kona depart from either Chicago O’Hare International Airport (ORD) or Chicago Midway Airport (MDW). Of the two Chicago airports, ORD handles more flights to Kailua-Kona than MDW. Therefore, consider flying from ORD to get more flight options.
  • Consider flying from Chicago MDW to Ellison Onizuka Kona International Airport (KOA) if you want to avoid long queues at the departure airport. MDW is usually less crowded than ORD. Therefore, you will spend less time getting through the airport for your flight.
  • Consider booking American Airlines or United when flying from Chicago ORD to Kailua-Kona. The airport is a hub for these two airlines; therefore, flying with them will give you more flight options. You will also get a way to access United Club and American Airlines Admirals Club at ORD by paying at the door.
  • You are welcome to use the pet relief areas at ORD when traveling with your pet from Chicago to Kailua-Kona. Outdoor pet relief areas are outside Door 1A, Door 2A, Door 5B, and near Lotto Booth in Terminal 1 Main Hall.
See more tips

Top 4 airlines serving from Chicago to Kailua-Kona

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Kailua-Kona. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Kailua-Kona? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Alaska AirlinesOverall score based on 9137 reviews
8.2Boarding
7.3Entertainment
7.3Food
7.9Comfort
8.6Crew
Airline reviews

Boarded the plain and had to wait 1 hour for crew Captain to arrive from another flight

4.0 OkayRandy, May 2024SFO - SEA
Read more about Alaska Airlines reviews

Boarded the plain and had to wait 1 hour for crew Captain to arrive from another flight

It was fine since it ensure we went to our destination in time.

Comfortable seat, plenty of leg room which is so rare, overhead bin comfortably accommodated my carry-on bag. Deli box was tasty, service was good, bathrooms were clean. Uneventful flight, which I appreciate. Departed on time and landed early.

The maintenance delay was seemingly handled very poorly... Little to no information was provided to the passengers sitting on board for an extended period of time. On a brighter note, at least the cabin crew (flight attendants) did the best they could. They seemingly were provided very little information with regards to the delay. Unless absolutely beyond my control, I can’t imagine buying a ticket on Alaska airlines again, based on this and a previous experience my wife recently had, along with complaints overheard from other passengers.

Honestly, there was not much they could do. Due to wind, the flight was delayed for several hours because we had to be diverted to San Jose where we needed to refuel before departing to Hawaii. Wish they had offered some snacks during the delays/diversion because we had to wait such a long time to finally get our food served during the flight after leaving California.

While the flight and the legroom was good boarding took a long time. The different groups Boarding made no sense as those in the back of the flight boarded last causing delays as people try to find room for their luggage in the upper bins. While there were plenty of seats on the flights We were spaced so that some rows were filled and others were empty. My first flight was very crowded and uncomfortable. On the way back both flights did not have Wi-Fi nor the entertainment package. We were only made aware of this a few hours before the flight. Since the flight was in the morning, I was asleep and was not able to download Books or other media to my phone. This is my first time flying Alaska airlines and I will admit to thinking twice before I do so again.

Our flight was delayed by six hours, our plane never left Portland the night before but the airline didn’t inform anyone till two hours before a six am flight. The plane, our plane never left the west coast! No plane no flight, simply let folks know when you know, not hours and hours later. No one apologized, no one said much of anything, we were just expected to wait quietly and await instructions.

I liked the fast internet and twice serving of snacks and drinks. Paid food options could have included more.

I’m a first time mom and traveled with my 18mo old boy and it was not a great experience with the flight attendants. They were not friendly or helpful at all. It’s hard enough traveling with a toddler and have people be rude and unkind does not help.

Pretty terrible. The aisles on this flight were too narrow so we had to carry our baby, care seat, luggage, travel stroller step by step down the aisle slowing down a lot of passengers in the process. Not only was this a safety hazard but remember that scene from game of thrones where Cersei walks naked through the streets? It felt about as excruciating as that except both me and my husband were carrying 50lbs of weight while everyone from the flight attendants and passengers dolled out comments like “that stroller doesn’t fit in the overhead compartment and you should check it at the gate” when it is a travel stroller that absolutely fits and did fit in the overhead compartment. The flight said it was 30 min delayed but in actuality we did not take off until 1.5 hours past the original time. It was absolutely terrible. Alaska also charged us 200 dollars just in baggage fees even tho we took the time to buy two check on baggages via their app and bought an extra seat for our child and they still refused to overlook our first time flying with them. Everyone in general looked super miserable and traveling with them with a child is pretty much untenable. Lastly I originally thought I had booked an AM flight for my family but it was a PM flight which I knew was not going to end well since we had a 1.5 year old with us on a flight that gets in 9p. I ended up calling Alaska to try to change the first leg for a change fee, and would even have accepted half of a refund to book a completely different flight but of course they refused and absolutely allowed no flexibility to plans so I guess my revenge was our baby cried for 3 out of the four hour flight and hopefully convinced every miserable person on that flight to never fly Alaska again 🤷🏻‍♀️

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

Left 2 hours later for delayed I had to take care a kid with special need since people don’t want to move to accommodate the rest of the family. . It wasn’t bad but that made me upset that people can be that selfish.

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Everything was great, only problem was that flights were delayed

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Book cheap flights from Chicago to Kailua-Kona

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Kailua-Kona found on KAYAK in the last 72 hours.
5/31ven.
1 stopAlaska Airlines
19h 59mORD-KOA
$211
8/24sam.
1 stopAlaska Airlines
33h 00mORD-KOA
$217
9/15dim.
1 stopDelta
14h 56mORD-KOA
$250
7/15lun.
1 stopDelta
14h 34mORD-KOA
$251
9/15dim.
1 stopDelta
14h 56mORD-KOA
$258
8/10sam.
1 stopAmerican Airlines
11h 52mORD-KOA
$263
8/24sam.
2 stopsUnited Airlines
13h 29mORD-KOA
$286
5/10ven.
1 stopAmerican Airlines
11h 35mORD-KOA
$305
7/16mar.
1 stopUnited Airlines
13h 27mORD-KOA
$349
5/31ven.
3 stops
30h 15mORD-KOA
$358

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Last minute flights from Chicago to Kailua-Kona

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Kailua-Kona that are departing in the next 10 days.
5/7mar.
multi-stopDelta
16h 30mORD-KOA
5/9jeu.
multi-stopDelta
10h 54mKOA-ORD
$562
5/7mar.
multi-stopDelta
16h 30mORD-KOA
5/9jeu.
multi-stopDelta
16h 42mKOA-ORD
$567
5/7mar.
multi-stopDelta
13h 59mORD-KOA
5/9jeu.
multi-stopDelta
16h 42mKOA-ORD
$572
5/9jeu.
multi-stopAlaska Airlines
30h 34mORD-KOA
5/18sam.
multi-stopAlaska Airlines
28h 27mKOA-ORD
$609
5/9jeu.
multi-stopAlaska Airlines
30h 34mORD-KOA
5/20lun.
multi-stopAlaska Airlines
27h 38mKOA-ORD
$624
5/9jeu.
multi-stopDelta
16h 30mORD-KOA
5/20lun.
multi-stopDelta
13h 00mKOA-ORD
$625
5/9jeu.
multi-stopAlaska Airlines
30h 34mORD-KOA
5/18sam.
multi-stopAlaska Airlines
27h 27mKOA-ORD
$666
5/9jeu.
multi-stopDelta
15h 50mORD-KOA
5/20lun.
multi-stopDelta
15h 44mKOA-ORD
$686
5/9jeu.
multi-stopAmerican Airlines
15h 28mORD-KOA
5/18sam.
multi-stopAmerican Airlines
14h 20mKOA-ORD
$745
5/7mar.
multi-stopDelta
13h 49mMDW-KOA
5/8mer.
multi-stopDelta
15h 24mKOA-MDW
$812

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Flights to Kailua-Kona

Destination:

Kailua-Kona (KOA)United States

Return flight deals:

Kailua-Kona - Chicago

Cabin classes:

$2,171
$5,385
$1,760
$1,893