$160 Find Cheap Flights from Chicago to Alaska

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 Alaska departing on 11/10. 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 Alaska

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Alaska, 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 Alaska, as well as popular online travel agencies
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Cheap Flights from Chicago to Alaska

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Anchorage
Anchoragenonstop$318
Fairbanks
Fairbanks1 stop$365
Anchorage
Anchoragenonstop$318
Fairbanks
Fairbanks1 stop$365

Book Cheap Chicago to Alaska Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Alaska 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 Chicago to Alaska

Sat, Nov 1 - Sat, Nov 8
United Airlines Logo
4:05 pm - 7:59 pmORD-ANC
6h 54mnonstop
United Airlines Logo
9:07 pm - 6:09 amANC-ORD
6h 02mnonstop
$318United Airlines
Find Deal
Sun, Mar 29 - Sun, Mar 29
Alaska Airlines Logo
7:00 am - 6:20 pmORD-ANC
14h 20m1 stop
Alaska Airlines Logo
9:00 pm - 6:51 amANC-ORD
6h 51mnonstop
$322Alaska Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8
United Airlines Logo
4:05 pm - 7:59 pmORD-ANC
6h 54mnonstop
United Airlines Logo
11:59 pm - 1:15 pmANC-ORD
10h 16m1 stop
$328United Airlines
Find Deal
Sat, Apr 11 - Sun, Apr 19
Alaska Airlines Logo
7:00 am - 1:20 pmORD-ANC
9h 20m1 stop
Alaska Airlines Logo
9:00 pm - 6:51 amANC-ORD
6h 51mnonstop
$336Alaska Airlines
Find Deal
Mon, Nov 24 - Fri, Nov 28
Delta Logo
7:02 pm - 12:56 amMDW-ANC
8h 54m1 stop
Delta Logo
6:05 am - 6:18 pmANC-MDW
9h 13m1 stop
$338Delta
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Fri, Nov 21 - Fri, Nov 28
Delta Logo
7:47 am - 4:42 pmORD-ANC
11h 55m1 stop
Delta Logo
6:05 am - 8:30 amANC-ORD
23h 25m1 stop
$339Delta
Find Deal
Mon, Nov 3 - Sun, Nov 9
Hawaiian Airlines Logo
6:00 am - 12:55 pmORD-FAI
9h 55m1 stop
Hawaiian Airlines Logo
4:10 pm - 6:22 amFAI-ORD
11h 12m1 stop
$365Hawaiian Airlines
Find Deal
Mon, Nov 3 - Sun, Nov 9
Hawaiian Airlines Logo
6:00 am - 12:55 pmORD-FAI
9h 55m1 stop
Hawaiian Airlines Logo
5:55 am - 12:24 amFAI-ORD
15h 29m1 stop
$390Hawaiian Airlines
Find Deal
Tue, Mar 10 - Wed, Mar 11
American Airlines Logo
9:45 am - 7:12 pmORD-JNU
12h 27m1 stop
American Airlines Logo
7:15 am - 7:45 pmJNU-ORD
9h 30m1 stop
$763American Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
American Airlines Logo
7:15 am - 1:27 pmORD-JNU
9h 12m1 stop
American Airlines Logo
6:55 am - 9:07 pmJNU-ORD
11h 12m1 stop
$784American Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to Alaska flights

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

How much is a round-trip flight from Chicago to Alaska?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Alaska departing in November.

What is the cheapest Chicago to Alaska flight route?

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

The cheapest ticket to Alaska from Chicago found in the last 72 hours was to Anchorage, at $318 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Anchorage (ANC), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $318.

Can I save money by flying with a layover from Chicago to Alaska?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $458, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to Alaska?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Alaska, 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 Alaska is April, when tickets cost $386 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $644 and $588 respectively.

What’s the cheapest day of the week to fly from Chicago to Alaska?

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

For Chicago to Alaska, Wednesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Alaska back to Chicago, the best deals are generally found on Tuesday, with Saturday being the most expensive.

How far in advance should I book a flight from Chicago to Alaska?

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 Alaska, 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 Alaska, you should book around 4 weeks before departure, which saves you about 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$160
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Chicago O'Hare Airport to Anchorage

FAQs - booking Alaska flights

  • I want to visit Juneau, Alaska, from Chicago. How should I get there?

    If you’d like to fly from Chicago to Alaska’s capital city of Juneau, start with a flight from Chicago O’Hare Airport (ORD) or Chicago’s Midway Airport (MDW) to Anchorage Airport (ANC). Upon arriving in Anchorage, you can take a nonstop flight to Juneau International Airport (JNU). Alternatively, you can take a layover flight from O’Hare Airport or Midway Airport to Juneau International Airport with a stopover at Seattle-Tacoma Airport (SEA).

  • Are there any nonstop flights from Chicago to Alaska?

    If you’d like a non-stop flight from Chicago to Alaska, fly out of Chicago O’Hare International Airport (ORD). United Airlines and Alaska Airlines offer nonstop service from O’Hare International Airport to the Ted Stevens Anchorage International Airport (ANC). Chicago’s Midway Airport (MDW) only offers layover flights from Chicago to Alaska.

  • I’m flying from Chicago to Alaska to visit Denali National Park. Where should I fly to?

    If you want to visit Denali National Park in Alaska from Chicago, consider flights from Chicago O’Hare Airport (ORD) or Chicago Midway Airport (MDW) to Fairbanks International Airport (FAI). United Airlines provides non-stop flight service, while both Delta and Alaska Airlines provide layover flights with a stop at Seattle-Tacoma International Airport (SEA). From Fairbanks, a train goes directly to Denali National Park, taking around 4 hours.

  • Are there any flights from Chicago to the Arctic region of northern Alaska?

    Although there aren’t any direct flights from Chicago to the Arctic region of Alaska, you can reach that area with multiple flights. First, fly from either Chicago O’Hare Airport (ORD) or Chicago Midway Airport (MDW) to Anchorage Airport. From Anchorage Airport (ANC), you can take nonstop flights to the Arctic towns of Barrow (around 2 hours), Deadhorse (about 1h 40min), Kotzebue (around 1h 30min), and Nome (about 1h 30min).

  • How does KAYAK find such low prices on flights from Chicago to Alaska?

    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 Alaska.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Alaska 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 Alaska?

    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 from Chicago to Alaska with an airline and back with another airline.

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

    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 from Chicago to Alaska up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Alaska?

    The cheapest time of day to fly to Alaska is generally in the afternoon, when round-trip flights cost $436 on average. Morning departures are around 1% more expensive than evening flights, on average. The most expensive time of day to fly to Alaska is generally in the morning, which is peak travel time and where the average cost of a ticket is $589.

Top tips for finding cheap flights to Alaska

  • If you’d like to relax before a long flight from Chicago to Alaska, Chicago O’Hare Airport (ORD) offers multiple lounges with daily passes. The American Airlines Admirals Clubs are in Concourses G, H, K, and L, while the United Clubs are in Concourses B, C, and F.
  • Both Chicago’s O’Hare Airport and Chicago Midway Airport (MDW) offer facilities and services for passengers with reduced mobility. These include accessible parking, accessible entrances, accessible bathrooms, and wheelchair assistance upon request.
  • If you’re looking for eco-friendly flights from Chicago to Alaska, both United Airlines and American Airlines are committed to net-zero carbon emissions by 2050. Alaska Airlines aims for the same by 2040. All three airlines seek to improve their fuel efficiency, as well.
  • Carry-on luggage policies for American Airlines, Delta, and United Airlines flights from Chicago to Alaska include a small personal item and a larger carry-on item that doesn’t exceed 22 lb. Their checked bag allowance includes up to two bags for a modest fee, with each bag measuring up to 62 linear inches.
  • Are you looking to save money on your flight from Chicago to Alaska? If you’re flexible on time, one-stop or two-stop flights tend to be cheaper than nonstop flights to Alaska. Sun Country Air flights have one stop at Minneapolis St Paul Airport (MSP), while Alaska Airlines stops at San Francisco Airport (SFO) and Seattle-Tacoma Airport (SEA).

Reviews of the top 5 airlines serving from Chicago to Alaska

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Alaska. 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 Alaska? 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 11069 reviews
7.1Food
7.8Comfort
7.0Entertainment
8.5Crew
8.1Boarding
Airline reviews

Great if it’s not a long flight in coach.

2.0 MediocreWendy, Oct 2025LAX - ANC
Read more Alaska Airlines reviews

Great if it’s not a long flight in coach.

Flight was delayed about 40 minutes by a mechanical problem. This made a long day even longer. Otherwise good.

After we boarded there was quite a long time before we actually took off, and there were no announcements from crew about why we were delayed. Later when they did make announcements they were largely inaudible. There was no food (other than for purchase) on the flight and no entertainment. Thats not a complaint, just explaining my ratings in those categories. The flight was smooth. Baggage claim was rapid.

Flight attendant missed us first pass with beverage. We had to ask for water on second pass as we were going to be missed again.

I read online that flights longer than 2500 miles also got a complimentary snack pack which did not happen. It just helps break up the long flight when you get a snack here and there. Apreciated the coke and coffee though. Everything was on time and I feel like we maybe arrived earlier than expected as well. I cannot complain.

Jammed up security line. Security personnel excellent but facility is really cramped and lines long. Alaska Airlines was excellent.

We were flying 1st class for a special occasion. This was a Hawaiian airlines flight. It was exceptional. Very comfortable seats and space. Extremely attentive crew. Food was great for airline food. They provided tablets to watch and full headphones to listen. This was the best airline experience I have had in decades.

you could have gotten me there on the day I was supposed to be there, not a day later. Paid for 3 nights at a VRBO and got to spend only 2 nights there.

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.

I requested wheelchair assistance in Seattle transferring gates and in Anchorage to get to baggage claim. No assistance was provided at all.

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

The flight was an hour and a half late departing which was inconvenient

Delay in SLC jammed us up in Chicago. Got caught up in rush hour traffic

The crew took good care of us. The flight from ATL to SFO is a longer one, and there were multiple beverage offerings. I like the 757's that Delta uses. Good airplane that is comfortable. I do wish Delta would separate Priority boarding from the better seats. I would gladly take a smaller seat in an open row than be jammed into Comfort just to get priority boarding, just to make sure I don't have to check a bag.

The flight was great. The gate location was way to far away!!!

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Gate agent rushed to fill hot jetway with crowd so it took over 12 minutes to go from gate to plane. Just like a discount airline Pooly prepared cabin and third time that claim of rough air prevented any cabin service. Friends on a Southwest flight at similar time had service.

Cramped seating for me. Luckily it wasn’t a long flight

Lounge in Lagos is terrible, food on board from Lagos to Atlanta was horrible. Only bright spot the cabin crew were awesome.

The staff and the boarding procedure were all amazing . The one flight was not equipped with WIFI which now adays seems odd. All in all the experience was good

The food options were limited and very specific. Some type of entertainment option for a 4.5 hour flight would have been nice.

Flight was smooth and comfortable. We were able to check a bag at counter due to full flight and boarded with an earlier group. We were there very early and didn’t hear the gate change just noticed our flight was no longer displayed st the gate. There were two other flights with gate shuffles - may be unavoidable but not desirable. First time I had to print my own luggage tag and attach at arrival. Not a fan of that process.

The crew was EXTREMELY helpful And sweet and the flight was smooth!

I received an email from Kayak with confirmation number for Hawaiian and another for Alaska. I received emails from Kayak for both my outbound and return flight to say "time to check in." Despite trying each number (Hawaiian and Alaska), I could not check in for outbound or return. It was then confusing at the airport - I hda "no place to go" to figure out how to check in. All the kiosks are marked "scan bag,etc." I wandered around with no agent to talk to. That was a bit stressful. Either Kayak, or airline, needed better communication on what to expect and to do.

Everything was great and smooth. Given the short flight there was no entertainment but the rating does not give this option. My first flight with Hawaiian was a success all around.

When I purchased my ticket, it said i was flying with Hawaii airlines. Which is now operated by Alaska. Naturally I went to check in with Hawaii airlines once at the airport. However, there was no one at the desk until 7 am and their kiosk couldn’t find my tickets. I went over to Alaska and they said they couldn’t help me and to wait for Hawaii. My flight left at 7:15 so I didn’t have time to wait. They even told me to ask United which was next to the Hawaii desk what time Hawaii opened. I called the Hawaii airlines number and the operator told me to ask Alaska for help since my flight was operated by Alaska. So I went back and almost got brushed off again and sent to Hawaii. The Alaska desk attendant told me to check in at their kiosk but it didn’t work. I ran over to an older lady who was helping check bags and asked for help printing my boarding passes. Thankful she was able to do it right away! This whole debacle took a little over an hour. I wish there was better communication and knowledge between the two airlines because it could have been easily handled if everyone between the two airlines was on the same page. Once I ran through the airport to get to my gate, we were greeted with a smile and they seemed glad we made our flight! We were the last to board and barely made it. After the headache our flight was great! No complaints there.

Biggest issue: awfully narrow seats, + not a lot of leg room. Other than that, everything was good. Cabin crew seemed like very nice people.

The Kayak confirmation number did not work for checking in the day before. I checked in at 8.30 using my ticket number. When I arrived at the airport, I was informed that the flight was overbooked, and since I had checked in late, I did not have a seat. The Next flight was not until ten PM. I called my wife, who had been taking care of our kids all weekend, and she was upset, calling me a liar and telling me to stay in SD. It turned my weekend getaway into a nightmare! I blame the Kayak website and will not book flights using your app in the future.

comfortable but the food is horrible. I have flown Hawaiian several times now and no matter what they say the food is its the same squashed bread with melted goop inside. Tastes fake and isnt what they represent, its quite nasty. What happend to real food? And there is NO entertainment!! so not sure why they are asking for a review on that.

Good and friendly staff. Nicely enjoyed the complimentary drink and snack.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

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

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

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

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

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.

Everything you need to know for your flight from Chicago to Alaska

Cabin class types available on flights to Alaska

Cabin classes available on flights to Alaska. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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