ORD - KOA

$223 Find Cheap Flights from Chicago O'Hare Airport 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 O'Hare Intl to Kailua-Kona departing on 10/21. 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 O'Hare Intl to Kailua-Kona (ORD-KOA)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl 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.

Recent round-trip flight deals from O'Hare Intl to Kailua-Kona

Wed, Dec 3 - Wed, Dec 10
Alaska Airlines Logo
3:05 pm - 12:55 pmORD-KOA
25h 50m2 stops
Alaska Airlines Logo
2:20 pm - 2:09 pmKOA-ORD
19h 49m1 stop
$431Alaska Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 10
Alaska Airlines Logo
7:59 pm - 3:48 pmORD-KOA
23h 49m2 stops
Alaska Airlines Logo
6:00 am - 11:50 pmKOA-ORD
13h 50m2 stops
$436Alaska Airlines
Find Deal
Wed, Nov 5 - Thu, Nov 13
Alaska Airlines Logo
2:54 pm - 10:34 amORD-KOA
23h 40m2 stops
Alaska Airlines Logo
8:45 am - 12:24 amKOA-ORD
11h 39m1 stop
$443Alaska Airlines
Find Deal
Wed, Oct 22 - Tue, Nov 4
Alaska Airlines Logo
8:00 am - 3:57 pmORD-KOA
12h 57m1 stop
Alaska Airlines Logo
12:09 pm - 6:59 pmKOA-ORD
26h 50m1 stop
$445Alaska Airlines
Find Deal
Mon, Nov 10 - Tue, Nov 11
Delta Logo
7:47 am - 6:13 pmORD-KOA
14h 26m1 stop
Delta Logo
8:30 pm - 1:34 pmKOA-ORD
13h 04m1 stop
$447Delta
Find Deal
Wed, Nov 5 - Thu, Nov 13
Alaska Airlines Logo
2:54 pm - 10:34 amORD-KOA
23h 40m2 stops
Alaska Airlines Logo
7:47 pm - 4:57 pmKOA-ORD
17h 10m2 stops
$448Alaska Airlines
Find Deal
Wed, Oct 1 - Wed, Oct 8
United Airlines Logo
6:15 am - 11:56 amORD-KOA
10h 41m1 stop
United Airlines Logo
10:00 pm - 1:32 pmKOA-ORD
10h 32m1 stop
$467United Airlines
Find Deal
Wed, Oct 8 - Wed, Oct 22
Delta Logo
7:37 am - 7:23 pmORD-KOA
16h 46m2 stops
Delta Logo
9:30 pm - 5:10 pmKOA-ORD
14h 40m1 stop
$471Delta
Find Deal
Thu, Oct 30 - Fri, Nov 7
Delta Logo
7:37 am - 5:30 pmORD-KOA
14h 53m1 stop
Delta Logo
9:30 pm - 9:19 pmKOA-ORD
19h 49m2 stops
$473Delta
Find Deal
Fri, Oct 31 - Mon, Nov 10
United Airlines Logo
8:47 am - 3:18 pmORD-KOA
11h 31m1 stop
United Airlines Logo
2:20 pm - 5:16 amKOA-ORD
10h 56m1 stop
$477United Airlines
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Security lines at ORD can exceed 30 minutes.
For a smooth arrival at KOA, consider renting a car.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Alaska Airlines
Cheapest • from $431 (round-trip)
Alaska Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 22% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 18% price drop
January
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$431
Overall average: $839
Alaska Airlines
Wed 12/3Wed 12/10
ORD - KOA • 2 stops
Cheapest non-stop
$2,774
United Airlines
Sat 2/14Sat 2/21
ORD - KOA • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Kailua-Kona!
Expert advice

Expert advice for your flight from O'Hare Intl 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

Security lines at ORD can exceed 30 minutes during peak times. Arrive early to ensure a smooth departure experience.

Read more about ORDby Stefanie Waldek
KOA

For a smooth arrival at KOA, consider renting a car. Major rental companies are available, but expect waits during peak times.

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 O'Hare Intl to Kailua-Kona flights

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

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

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

If you are looking for a flight deal from Chicago O'Hare Airport to Kailua-Kona, look for departures on Tuesdays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Kailua-Kona, Monday is the cheapest day to fly and Saturday is the most expensive.

What is the cheapest month to fly from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport to Kailua-Kona is January, where tickets cost $577 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is $839 and $812 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport 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 seasonAugust
Cheapest flight$223
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 18% lower on average.
Flight from Chicago O'Hare Airport to Kailua-Kona

When to book flights from O'Hare Intl to Kailua-Kona

Are your dates flexible? Find out the best times to travel from O'Hare Intl 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 Chicago O'Hare Airport to Kailua-Kona flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Kailua-Kona?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Kailua-Kona was $223 for a one-way ticket and $431 for a round-trip.

  • Do I need a passport to fly between Chicago O'Hare Airport and Kailua-Kona?

    No

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

    Chicago O'Hare Airport airport is called Chicago O'Hare Intl and the only airport in Kailua-Kona is Kona Intl.

  • Which aircraft models fly most regularly from Chicago O'Hare Airport to Kailua-Kona?

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

  • Which airline alliances offer flights from Chicago O'Hare Airport to Kailua-Kona?

    oneworld, SkyTeam, and Star Alliance are the airline alliances operating flights between Chicago O'Hare Airport 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 O'Hare Airport?

    Los Angeles is the most popular layover city among KAYAK users traveling from Chicago O'Hare Airport 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 $657 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 $717 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport 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 O'Hare Airport to Kailua-Kona.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport with another airline. Booking your flights between Chicago O'Hare Airport and KOA can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport 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 O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from O'Hare Intl 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 O'Hare Intl 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
8.1Boarding
7.1Food
7.8Comfort
8.5Crew
7.0Entertainment
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.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

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!

Love you guys are so friendly and kind and wonderful

Hawaiian airlines has awful customer service. Told me to keep a flight I wasn’t boarding, instead of rebooking me under two separate reservations, which caused my whole reservation to be canceled. Major issues with leadership and management. The staff at Hilo was reluctant to give me a refund, so I had to by a first class ticket in order to get on a flight the same time as my partner. The blame was pointed at me without sincere apology until the supervisor came out, who also apparently had no authority to refund me. Still waiting on correspondence from the airline days later.

I could not believe that on a 5 hour plus flight we were not given a complimentary meal . That should be illegal. Or it would be nice to be informed beforehand that a complimentary meal would not be provided. The wording in the email I got about pre ordering food was phrased in a way that made the food seem like it would be free. Very misleading! Also during boarding we were informed there would be empty seats we could move to if we wanted, all we had to do was wait for an announcement, however an announcement was never made. Then when we tried to change seats ourselves we were singled out over the loud speaker and told we could not move without asking. Then the flight was about to take off , so we didn’t have time to ask . Then we were told we could not move to the exit row because you had to pay for those seats, but we were not told where we could move. Also no one was in the exit rows so , if something happened no one would be there to assist the passengers. Also people should be allowed to move there if the airline wasn’t able to sell them. One passenger asked if he could pay for the upgrade and the flight attendant said she did not have the capability to charge for the seat on her mobile device, so the airline ended up losing possible income anyways . So why not let people move there during flight if you have no way to charge them? Then the landing was bumpy and awful and many passengers complained out loud when we landed .

The flight was great! The flight attendants were friendly and attentive. I would definitely fly Hawaiian Aurlines again!

You have to buy the ear buds and they only offers little cup of water twice.

Flight was on time, crew was friendly and prompt with the service. The only thing that could be improved is the seat space, but that's wishful thinking

Cons: Rode a newer Airbus - had the same rattle in the panels above my seat (plastics not secure b/t lighting and panels) as the last Airbus I rode. Cabin was quite warm, borderline hot. Asked to pay for headphones. And the reason I am writing this - when we arrived it took over 20 minutes to get our door open due to nobody on the ground ready for arrival. Likes: Staff was friendly, helpful, and professional. Sandwich was quite good.

The worst flight experience I've ever had. Our flight was delayed 14 whole hours because the flight crew never showed up. We had to wait in a two hour line to get our new boarding passes, we were told we had no other option but to fly at 10pm (we didn't depart until 11:45pm). Everyone had to contact their hotels and car rental places, workplaces, etc. since we lost an entire day's worth of travel. The crew showed up at 10:15, which was past the time we were supposed to board. They were laughing and being completely smug when they boarded, and they took another hour to board us onto our flight. The flight crew never came to check in on us, we were quickly given one drink and sandwich and they turned off the lights and were negligent the rest of the trip. My mom asked three attendants for a seat belt extender, they never brought one. I was dehydrated and never received another drink. They were very rude and unfriendly, we had been up since 4am the morning of our flight and didn't land in our destination until 2am the next day (5am local time). This was unacceptable service and treatment, these flights are not cheap and we were inconvenienced out of an entire day of travel. This was 100% avoidable and was the fault of Hawaiian Airlines, and their crews inability to show up to work on time.

Loved the leg room, usb charging, outlet, food, staff. The seats were very uncomfortable for some reason and made my buttocks ache and would have liked to be seated together from the time of purchasing tickets without having to pay extra.

Usually we have a pleasant trip on HA. Not this time! All stewards were unpleasant, rude, rushed, condescending. First step onto the plane, WE greeted the crew with an “Hello!”. They greeted us with a terse smile then ignored us. Not a good start. Even over the PA announcements, they were rushed and unpleasant. One Stewart even berated a passenger in front of us when all they asked is if the purchase cart had vodka to purchase. The steward said “LIKE WE SAID OVER THE PA, THIS ONLY HAS FOOD OR BEVERAGE!” Vodka is a beverage! It was a legitimate question. Not sure why she treated the passenger this way. Taking trash was even unpleasant, No “Thank you” or at least a smile. I work in CS. I know good CS can make or break your trip. There was absolutely no “aloha” on this trip. All clearly did not want to be on this plane and felt strongly that they did not want to provide a premium service to their clients. This might be our last HA and cancellation of my HA-MC if we are treated the same way going home. We are typically treated with kindness and warmth in the past with HA. This trip was unacceptable.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

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.

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 O'Hare Intl to Kailua-Kona

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