CHI - KOA

$205 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 9/27. 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
1 adult, Economy

KAYAK searches 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
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Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Kailua-Kona

Mon, Oct 27 - Tue, Nov 4
Alaska Airlines Logo
7:59 pm - 1:43 pmORD-KOA
22h 44m1 stop
Alaska Airlines Logo
12:09 pm - 1:54 pmKOA-ORD
21h 45m1 stop
$408Alaska Airlines
Find Deal
Mon, Sep 8 - Fri, Sep 12
Hawaiian Airlines Logo
8:00 am - 4:00 pmORD-KOA
13h 00m1 stop
Hawaiian Airlines Logo
12:16 pm - 5:00 amKOA-ORD
11h 44m1 stop
$409Hawaiian Airlines
Find Deal
Sun, Nov 9 - Wed, Nov 19
Southwest Logo
5:25 am - 1:40 pmMDW-KOA
12h 15m1 stop
Southwest Logo
9:15 pm - 11:35 amKOA-MDW
10h 20m1 stop
$409Southwest
Find Deal
Wed, Oct 8 - Wed, Oct 22
American Airlines Logo
7:00 am - 1:58 pmORD-KOA
11h 58m1 stop
American Airlines Logo
9:45 pm - 2:15 pmKOA-ORD
11h 30m1 stop
$410American Airlines
Find Deal
Wed, Oct 8 - Wed, Oct 22
American Airlines Logo
6:03 am - 1:58 pmORD-KOA
12h 55m1 stop
American Airlines Logo
9:45 pm - 2:15 pmKOA-ORD
11h 30m1 stop
$412American Airlines
Find Deal
Mon, Oct 27 - Thu, Nov 13
Alaska Airlines Logo
2:54 pm - 1:43 pmORD-KOA
27h 49m1 stop
Alaska Airlines Logo
6:00 am - 12:24 amKOA-ORD
14h 24m2 stops
$414Alaska Airlines
Find Deal
Wed, Sep 17 - Wed, Sep 24
Alaska Airlines Logo
6:20 am - 4:44 pmORD-KOA
15h 24m1 stop
Alaska Airlines Logo
8:00 am - 12:03 amKOA-ORD
11h 03m1 stop
$416Alaska Airlines
Find Deal
Sun, Sep 21 - Thu, Sep 25
Delta Logo
7:10 am - 5:29 pmORD-KOA
15h 19m1 stop
Delta Logo
9:30 pm - 1:20 pmKOA-ORD
10h 50m1 stop
$423Delta
Find Deal
Wed, Sep 17 - Wed, Sep 24
Delta Logo
6:15 am - 5:35 pmORD-KOA
16h 20m2 stops
Delta Logo
9:30 pm - 1:20 pmKOA-ORD
10h 50m1 stop
$429Delta
Find Deal
Tue, Nov 11 - Wed, Nov 19
Southwest Logo
5:15 am - 1:40 pmMDW-KOA
12h 25m1 stop
Southwest Logo
9:15 pm - 11:35 amKOA-MDW
10h 20m1 stop
$454Southwest
Find Deal
Expert advice

Expert advice for your flight from Chicago to Kailua-Kona

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
ORD

For a quick commute to downtown Chicago from ORD, take the CTA Blue Line train, which runs 24 hours and avoids traffic delays.

Read more about ORDby Stefanie Waldek
KOA

For a smooth arrival at KOA, consider renting a car. Major rental companies are available, and shuttles are conveniently located.

Read more about KOAby Blane Bachelor
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Blane Bachelor

Blane Bachelor

Expert on KOA

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more
Booking Insights

KAYAK's insights & trends for Chicago to Kailua-Kona flights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Kailua-Kona costs $1,243 on the route between Chicago O'Hare Intl Airport (ORD) and Kailua-Kona (KOA). It is also the most popular route.

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

The average price of all round-trip flights from Chicago to Kailua-Kona clicked on KAYAK for each day over the last 12 months.

For Chicago to Kailua-Kona, Tuesday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Kailua-Kona back to Chicago, the best deals are generally found on Monday, with Saturday being the most expensive.

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 round-trip 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 September, where tickets cost $542 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $951 and $951 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.

To get a below average price on the flight from Chicago to Kailua-Kona, you should book around 2 weeks before departure, which saves you about 22% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$205
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 34% 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 $205 for a one-way ticket and $408 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 Southwest?

    The two airlines most popular with KAYAK users for flights from Chicago to Kailua-Kona are Alaska Airlines and Southwest. With an average price for the route of $688 and an overall rating of 8.0, Alaska Airlines is the most popular choice. Southwest is also a great choice for the route, with an average price of $804 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.

KAYAK’s top tips for finding a cheap flight from Chicago to Kailua-Kona

  • 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.

Reviews of the top 5 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 10000 reviews
7.8Comfort
7.0Entertainment
8.5Crew
7.1Food
8.1Boarding
Airline reviews

Would have been nice if my flight was on time and I didn't miss my connection and had to spend the night in Seattle, losing one night at the VRBO I paid for in Sitka. And, my connecting flight was still at the gate when my flight was taxiing to it's gate. But, it took off. Too bad for me. I really can't believe you even want me to review or comment on my experience.

2.0 MediocreAnonymous, Aug 2025ORD - SEA
Read more Alaska Airlines reviews

Would have been nice if my flight was on time and I didn't miss my connection and had to spend the night in Seattle, losing one night at the VRBO I paid for in Sitka. And, my connecting flight was still at the gate when my flight was taxiing to it's gate. But, it took off. Too bad for me. I really can't believe you even want me to review or comment on my experience.

Terrible. Would never fly again. Took them several hours to prepare the plane and and reached my destination 4 hours late.

Our boarding was delayed due to two flat tires, but I appreciate the focus on safety. I also appreciated the additional offerings for drinks which never happened before except on Hawaiian Airlines. The hospitality is fantastic! Glad I upgraded to premium seats for the extra leg room as I was getting frustrated when the person in front of me was very restless and kept shifting. Otherwise, it was a fantastic experience.

Had to sit and wait to get off the plane for closeto a hour. My son also flying to a different destination that day also had like a 2.5 hr delay

Checking in very confusing compared to Hawaiian Airlines - much simpler! Front checking in at airport can improve. Hawaiian service always gives the extra mile, with a smile. Alaska can use and spread the Aloha Spirit. Mahalo nui loa Thank you 🤙

Very nice as always. Not that it’s anyone’s fault really but for some reason the seat (16C) was really hard…. Not typical for your planes… dunno what or why… maybe it was just me ?, The flight was great otherwise

Tickets we booked together in January became two different connecting flights. VERY PISSED a about this and a terrible start to our bucket list vacation

Could not check in online - had to get boarding passes at the ticket counter and our daughter got bumped off our connecting flight. NOT OK!

would have been nice for flight to not be delayed by 2 hours so that we had to pay $80 to get home since BART had shut down. i thought a 10pm arrival would leave enough time to account for delays but i was wrong.

I needed more space to sleep on an overnight flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

There was supposed to be a meal served, but there wasn’t and the major toilet was out of order

They made us board and then deboard due to mechanical issue which delayed the departure by almost 2 hours and we barely made our connecting flight. These quality checks should've been done before boarding not after.

Having to up charge for a seat assignment is not good. Delta can do better

I liked the friendliness of the staff. The cleanliness of all 3 planes.

Was charged for my luggage despite having been on one ticket from an international flight. Too tired to argue after 15 hours on flight. Was charged for rechecking it at JFK airport. Not sure why those off Kenya Airways were required to do that.

Stuck on tarmac for two hours plus a 5.5 hour flight. Rude flight attendant. And no meals, not even for purchase!

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

Everything you need to know for your flight from Chicago to Kailua-Kona

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