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CHI - KOA

$184 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 8/24. 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
Fri 7/12
Fri 7/19

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 44,148,666 times on KAYAK, and here is why:

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

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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
7:16 pm - 12:30 pmORD-KOA
22h 14m1 stop
3:09 pm - 12:09 pmKOA-ORD
16h 00m1 stop
$362Alaska Airlines
Find Deal
Thu, Oct 24 - Fri, Oct 25
7:26 am - 5:22 pmORD-KOA
14h 56m1 stop
9:45 pm - 1:18 pmKOA-ORD
10h 33m1 stop
$363Delta
Find Deal
Wed, Oct 30 - Wed, Oct 30
7:26 pm - 9:03 pmORD-KOA
30h 37m1 stop
8:28 pm - 4:37 amKOA-ORD
27h 09m1 stop
$364Alaska Airlines
Find Deal
Fri, Sep 13 - Mon, Sep 23
7:00 am - 5:07 pmORD-KOA
15h 07m1 stop
9:30 pm - 1:15 pmKOA-ORD
10h 45m1 stop
$365Delta
Find Deal
Fri, Sep 6 - Sat, Sep 14
3:24 pm - 9:07 pmORD-KOA
34h 43m1 stop
3:09 pm - 12:09 pmKOA-ORD
16h 00m1 stop
$366Alaska Airlines
Find Deal
Fri, Oct 18 - Fri, Oct 25
6:35 pm - 5:04 pmORD-KOA
27h 29m1 stop
9:30 pm - 11:59 pmKOA-ORD
21h 29m1 stop
$367Delta
Find Deal
Fri, Sep 13 - Tue, Sep 24
6:00 am - 9:07 pmORD-KOA
20h 07m1 stop
3:08 pm - 12:09 pmKOA-ORD
16h 01m1 stop
$368Alaska Airlines
Find Deal
Sun, Oct 20 - Mon, Oct 28
7:26 am - 5:22 pmORD-KOA
14h 56m1 stop
9:45 pm - 1:18 pmKOA-ORD
10h 33m1 stop
$369Delta
Find Deal
Tue, Oct 29 - Thu, Oct 31
5:50 am - 12:52 pmORD-KOA
12h 02m1 stop
9:39 pm - 3:50 pmKOA-ORD
13h 11m1 stop
$562American Airlines
Find Deal
Wed, Aug 21 - Fri, Aug 30
5:50 am - 12:52 pmORD-KOA
12h 02m1 stop
9:39 pm - 12:34 pmKOA-ORD
9h 55m1 stop
$584American Airlines
Find Deal
Wed, Aug 21 - Sun, Sep 1

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 $1,255 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 $740.

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 Wednesday 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 April, where tickets cost $548 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $996 and $842 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 64 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 ($184) and Delta ($329), and the lowest round-trip tickets were found on Alaska Airlines ($362) and Delta ($363).

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

$184
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 11% 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 $184 for a one-way ticket and $362 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 $679 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 $625 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 $776 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 9269 reviews
7.3Food
7.9Comfort
8.6Crew
8.2Boarding
7.3Entertainment
Airline reviews

The crew members were wonderful. When we encountered a little turbulence, the pilots let us know and provided an estimate of how long it would last. Another nice amenity: every seat has AC power outlets and USB ports. It was a 6-hour flight, which seems a bit much for a single-aisle jet: over 200 passengers with access to only 3 restrooms (assuming you time it right and won't be blocked in by beverage carts); food is mediocre, over-priced, and (if you failed to reserve a meal ahead of time) the flight attendants have to process food/meal sales in the aisle. To access any entertainment, you must use your own device to log on to the plane's wi-fi (or bring your own entertainment).

8.0 ExcellentNolan, Jun 2024SEA - HNL
Read more about Alaska Airlines reviews

The crew members were wonderful. When we encountered a little turbulence, the pilots let us know and provided an estimate of how long it would last. Another nice amenity: every seat has AC power outlets and USB ports. It was a 6-hour flight, which seems a bit much for a single-aisle jet: over 200 passengers with access to only 3 restrooms (assuming you time it right and won't be blocked in by beverage carts); food is mediocre, over-priced, and (if you failed to reserve a meal ahead of time) the flight attendants have to process food/meal sales in the aisle. To access any entertainment, you must use your own device to log on to the plane's wi-fi (or bring your own entertainment).

The people who worked for Alaska Airlines, both on the ground at O'Hare and during the flight, made it remarkable for me. Their customer service is incredible; they're kind of like the Nordstrom of the sky.

We loved the extra legroom on the flight and the fact that we didn’t have any one beside us.Everything was a n time and satisfactory.

Very close to on-time takeoff and landing. Attendants were all great - Julia was best! Joined the Alaska Air Rewards and will fly with them again!

Great first time experience for me. The gate agent at the Anchorage location was so helpful. Definitely will be booking more on Alaska.

Delayed an hour and sat without updates. Ended up an hour late to destination

The flight was decent again if there was a place that you could put crying children that would be great. Or maybe make a rule against allowing infants on the plane.

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.

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

I’ve had a couple flights this week on United that were delayed by an hour or more

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.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

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

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.
8/24Sat
1 stopAlaska Airlines
20h 03mORD-KOA
$184
8/24Sat
2 stopsAlaska Airlines
27h 39mORD-KOA
$243
7/20Sat
1 stopDelta
15h 07mORD-KOA
$329
7/1Mon
1 stopDelta
15h 11mORD-KOA
$346
7/22Mon
2 stopsUnited Airlines
18h 57mORD-KOA
$395
6/29Sat
1 stopUnited Airlines
11h 01mORD-KOA
$397
7/18Thu
1 stopUnited Airlines
18h 36mORD-KOA
$404
7/19Fri
1 stopUnited Airlines
11h 36mORD-KOA
$411
6/28Fri
1 stopAmerican Airlines
11h 36mORD-KOA
$421
6/30Sun
2 stopsAmerican Airlines
14h 05mORD-KOA
$556

Search by stops

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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.
6/17Mon
multi-stopAlaska Airlines
23h 52mORD-KOA
6/18Tue
multi-stopAlaska Airlines
27h 29mKOA-ORD
$731
6/16Sun
multi-stopUnited Airlines
13h 47mORD-KOA
6/30Sun
multi-stopUnited Airlines
13h 13mKOA-ORD
$750
6/16Sun
multi-stopUnited Airlines
13h 47mORD-KOA
6/30Sun
multi-stopUnited Airlines
16h 28mKOA-ORD
$755
6/16Sun
multi-stopAmerican Airlines
14h 05mORD-KOA
6/30Sun
multi-stopAmerican Airlines
14h 49mKOA-ORD
$806
6/17Mon
multi-stopAlaska Airlines
15h 14mORD-KOA
6/18Tue
multi-stopAlaska Airlines
26h 23mKOA-ORD
$862
6/17Mon
multi-stopUnited Airlines
13h 10mORD-KOA
6/18Tue
multi-stopUnited Airlines
15h 18mKOA-ORD
$882
6/17Mon
multi-stopDelta
17h 31mMDW-KOA
6/18Tue
multi-stopDelta
15h 56mKOA-MDW
$1,165

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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
$1,330
$740