$390 Find Cheap Flights from Caribbean to Anchorage

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Anchorage departing on 9/21. 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

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Cheap Flights from Caribbean to Anchorage

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

Thu, Oct 2 - Mon, Oct 6
Delta Logo
7:00 am - 1:37 amSJU-ANC
22h 37m2 stops
Delta Logo
9:45 pm - 4:25 pmANC-SJU
14h 40m2 stops
$745Delta
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Thu, Oct 2 - Mon, Oct 6
American Airlines Logo
7:05 pm - 8:48 pmSJU-ANC
29h 43m2 stops
American Airlines Logo
7:52 pm - 2:25 pmANC-SJU
14h 33m1 stop
$751American Airlines
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Thu, Oct 2 - Mon, Oct 6
American Airlines Logo
7:05 pm - 8:48 pmSJU-ANC
29h 43m2 stops
American Airlines Logo
7:52 pm - 3:54 pmANC-SJU
16h 02m2 stops
$752American Airlines
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Thu, Sep 18 - Thu, Oct 2
American Airlines Logo
6:10 am - 7:08 pmSJU-ANC
16h 58m2 stops
American Airlines Logo
8:13 pm - 2:15 pmANC-SJU
14h 02m1 stop
$754American Airlines
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Thu, Oct 2 - Sun, Oct 5
Delta Logo
7:30 am - 1:37 amSJU-ANC
22h 07m2 stops
Delta Logo
12:30 am - 9:59 pmANC-SJU
17h 29m2 stops
$755Delta
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Fri, Oct 10 - Sat, Oct 18
Delta Logo
12:51 pm - 1:59 amSJU-ANC
17h 08m2 stops
Delta Logo
8:15 pm - 11:41 amANC-SJU
11h 26m1 stop
$764Delta
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Wed, Oct 1 - Mon, Oct 6
United Airlines Logo
1:05 am - 7:57 pmSJU-ANC
22h 52m2 stops
United Airlines Logo
11:49 pm - 2:44 pmANC-SJU
34h 55m2 stops
$790United Airlines
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Wed, Oct 1 - Mon, Oct 6
United Airlines Logo
1:05 am - 7:57 pmSJU-ANC
22h 52m2 stops
United Airlines Logo
9:04 pm - 2:44 pmANC-SJU
13h 40m1 stop
$806United Airlines
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Fri, Oct 10 - Fri, Oct 24
Alaska Airlines Logo
3:10 pm - 1:22 pmSJU-ANC
26h 12m3 stops
Alaska Airlines Logo
1:59 pm - 2:25 pmANC-SJU
20h 26m2 stops
$1,041Alaska Airlines
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Fri, Oct 10 - Sat, Oct 18
Alaska Airlines Logo
3:10 pm - 1:22 pmSJU-ANC
26h 12m3 stops
Alaska Airlines Logo
10:50 am - 2:20 pmANC-SJU
23h 30m3 stops
$1,066Alaska Airlines
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Good to know

Low seasonMarch
Cheapest flight$390
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from San Juan to Anchorage

FAQs for booking flights from Caribbean to Anchorage

  • How does KAYAK find such low prices on flights from Caribbean to Anchorage?

    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 Caribbean to Anchorage.

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

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

    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 Anchorage with an airline and back to Caribbean with another airline.

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

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

Reviews of the top 3 airlines serving from Caribbean to Anchorage

 
Need help choosing which airline to fly with from Caribbean to Anchorage? 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
DeltaOverall score based on 7980 reviews
8.5Crew
8.2Boarding
7.9Entertainment
7.9Comfort
7.3Food
Airline reviews

Check in process was terrible. Lady at counter didn’t know what she was doing

4.0 OkayAnonymous, Jul 2025ICN - SEA
Read more Delta reviews

Check in process was terrible. Lady at counter didn’t know what she was doing

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

The crew was amazing; Von, Vera and Guadalupe were very friendly and attentive throughout the entire flight. They were friendly and welcoming to everyone. A solid and dedicated team for sure!

Terrible. I was bumped off of my original flight and spent the next six days fighting to get back on it. I lost hours of my vacation trying to get this situation corrected.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Terrible. Delayed 7 hours, and cancelled the flight, leaving me stranded and out of pocket $500 for an alternative last minute flight

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

Had one staff that was not pleasant. Seems they are stressed with too many people to care for.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Ok. Get a different kosher caterer. The food was odd.

Food was terrible. Crew was kind but skipped over my row for providing sandwiches and beverages.

Our flight was understandably diverted to a small regional airport in Laramie, Wyoming due to weather conditions, which I fully recognize and appreciate. However, the low rating stems from the experience that followed: passengers remained on board for over an hour without the option to deplane and stretch, despite the aircraft being stationary. Although the pilot opened the cabin door, only he was permitted to exit. Meanwhile, passengers grew increasingly uncomfortable as warm summer air entered the cabin through the open door, and being in the second row meant we were impacted immediately. While the flight attendants made efforts to keep everyone at ease, I believe allowing passengers to deplane briefly, given the extended delay, would have significantly improved the overall experience.

I never flew. Flight was canceled. DIA worst airport in the country. Avoid at all costs.

Lost luggage, they need a baggage service representative available all times in Atlanta

Our experience on United Airlines was extremely poor. The plane was extremely cold throughout our entire flight- which multiple people complained about- and we had to wait 2 hours to get a blanket which was too thin and barely helped warm us up. As well as this, none of the entertainment features were working so we had to sit through a roughly 10 hour flight with nothing to keep our attention, including the actual flight path screen. It was an extremely disappointing experience and I would hope that this gets fixed if we ever choose United Airlines again.

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

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

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Very clean and comfortable cabin. Amazing Mediterranean salad for lunch before landing. Great range of films to watch. Really quiet and easy to sleep on the flight also. The initial food was a bit weird: odd fried chicken pieces in some weird white gloop, but that would be my lack of cultural knowledge on the grub. Salad more than made up for it at the other end. Staff were super attentive and helpful. Great and easy flight

International baggage recheck process in Philadelphia was a disaster. Waited 1 hour and 45 minutes to receive our bags. Waited 15 minutes to recheck bags, flight notification boards were blank so we asked an AA representative for our connecting gate and we were directed to the wrong terminal and gate. Our connection window was over 3 hours and we made our flight by 5 minutes. We pulled away from the gate and sat on the runway for 1 1/2 hours. 1 of our 4 bags didn’t make it to Phoenix. The mobile app for lost baggage didn’t work, the AA rep had to manually fix.

I miss my flight and they could not rebook me that day because the other flight was full, and for the next day I had to pay a whole new fee again which I think is unprofessional

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

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