$319 Find Cheap Flights from Anchorage to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Anchorage to Caribbean departing on 1/11. 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, 0 bags

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Cheap Flights from Anchorage to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$931
Santo Domingo
Santo Domingo2 stops$881
Nassau
Nassau2 stops$721
Punta Cana
Punta Cana2 stops$931
Santo Domingo
Santo Domingo2 stops$881
Nassau
Nassau2 stops$721

Book Cheap Anchorage to Caribbean Plane Tickets

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

Wed, Nov 19 - Tue, Jan 13
Delta Logo
2:20 pm - 11:28 amANC-NAS
17h 08m2 stops
Delta Logo
1:41 pm - 12:50 amNAS-ANC
15h 09m2 stops
$721Delta
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Wed, Dec 10 - Wed, Dec 17
Delta Logo
5:37 pm - 1:59 pmANC-SJU
15h 22m2 stops
Delta Logo
3:10 pm - 1:53 amSJU-ANC
15h 43m2 stops
$744Delta
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Sun, Jan 18 - Fri, Jan 23
Delta Logo
3:00 pm - 2:10 pmANC-SJU
18h 10m2 stops
Delta Logo
6:15 am - 8:44 pmSJU-ANC
19h 29m2 stops
$824Delta
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Mon, Dec 1 - Fri, Jan 16
Delta Logo
12:30 am - 11:20 pmANC-SJU
17h 50m2 stops
Delta Logo
7:30 am - 6:58 pmSJU-ANC
16h 28m2 stops
$834Delta
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Mon, Apr 27 - Wed, Apr 29
United Airlines Logo
11:45 pm - 5:38 pmANC-SJU
13h 53m1 stop
United Airlines Logo
1:05 am - 12:57 pmSJU-ANC
15h 52m2 stops
$874United Airlines
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Mon, Apr 27 - Wed, Apr 29
United Airlines Logo
11:45 pm - 5:38 pmANC-SJU
13h 53m1 stop
United Airlines Logo
1:05 am - 12:57 pmSJU-ANC
15h 52m2 stops
$894United Airlines
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Sat, Mar 28 - Wed, Apr 1
American Airlines Logo
8:48 pm - 2:50 pmANC-PUJ
14h 02m2 stops
American Airlines Logo
5:05 pm - 6:37 pmPUJ-ANC
29h 32m2 stops
$1,041American Airlines
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Thu, Dec 11 - Sun, Jan 11
Multiple Airlines Logo
3:30 pm - 9:11 amANC-SDQ
36h 41m3 stops
Multiple Airlines Logo
3:35 pm - 11:56 amSDQ-ANC
49h 21m3 stops
$1,047Multiple Airlines
Find Deal
Sat, Mar 28 - Wed, Apr 1
American Airlines Logo
8:48 pm - 3:19 pmANC-PUJ
14h 31m1 stop
American Airlines Logo
12:50 pm - 6:37 pmPUJ-ANC
33h 47m1 stop
$1,064American Airlines
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Sun, Dec 21 - Wed, Jan 28
Multiple Airlines Logo
8:30 pm - 9:04 pmANC-STI
19h 34m2 stops
Multiple Airlines Logo
6:00 am - 12:54 amSTI-ANC
23h 54m2 stops
$1,546Multiple Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Anchorage to Caribbean flights

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

What is the cheapest month to fly from Anchorage to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Anchorage to Caribbean, 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 Anchorage to Caribbean is August, when tickets cost $441 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $1,272 and $1,246 respectively.

What’s the cheapest day of the week to fly from Anchorage to Caribbean?

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

If your flying dates are flexible, you should consider flying to Caribbean on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Thursday is the most expensive day to fly from Anchorage to Caribbean. For your return ticket, we recommend flying on a Monday and avoiding Fridays for the best deals.

Good to know

Low seasonAugust
Cheapest flight$319
Best time to beat the crowds with an average 57% drop in price.
Most popular time to fly with an average 25% increase in price.
Flight from Anchorage to Santo Domingo

FAQs - booking Caribbean flights

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

    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 Anchorage to Caribbean.

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

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

    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 Anchorage to Caribbean 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 Anchorage to Caribbean?

    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 Anchorage to Caribbean 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 Caribbean?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $1,008 on average. Morning departures are around 22% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $1,242.

Reviews of the top 3 airlines serving from Anchorage to Caribbean

 
Need help choosing which airline to fly with from Anchorage to Caribbean? 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 11275 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.1Food
7.0Entertainment
Airline reviews

Flight was delayed several times then eventually cancelled which caused issues with our hotel, car rental and tickets to planned event. We also spent unplanned expense with Lyft to and from the airport which was frustrating. Customer care was not present during whole time at the airport.

2.0 MediocreAnonymous, Oct 2025ANC - LAS
Read more Alaska Airlines reviews

Flight was delayed several times then eventually cancelled which caused issues with our hotel, car rental and tickets to planned event. We also spent unplanned expense with Lyft to and from the airport which was frustrating. Customer care was not present during whole time at the airport.

My flight was canceled because of an IT outage, and they did not answer the phone for 8 hrs. There was no next flight out, I have missed my wedding because of this.

Liked the crew. Multiple delays. Altered my complete day and plans

The plane was clean. They got us to the destination. It was very difficult to hear the announcements at the gate. The person was speaking way too quickly, and the sound system did not carry to all parts of the seating area at the gate. The flight left more than an hour late, which left many of the passengers missing connections.

The chicken salad was very small, the lettuce was wilted and there was no flavor. The hamburger was excellent.

Mostly good. Delayed which in my experience so far happens often with Alaska Airlines. Thank you.

We received a check-in reminder the day before the flight, and it listed the flight at a later time. Correct flight number, same seats, etc. for 3 hours later. I called the airline to confirm and they had no record of the email. The info was wrong, and we would have missed our flight if we'd assumed it was correct. I want to know where/how we received this incorrect info.

My experience would’ve been great because we were on a new plane, but they said as we boarded that the plane would be too new to have WiFi, which to me is unreasonable - newer planes should def have WiFi! It was a 5 hour flight from Anchorage to San Fran and because there was no WiFi, I had to take an unexpected half day off work, which was super annoying because I had a lot to do and we only found out a few minutes before takeoff.

5 1/2 hour trip. Nice plane. easy boarding. Could have used a bit more beverage service but it was a red eye flight and they didn't want to wake everyone.

Paid extra $230 to check frozen fish on arrival to LAX. I was told my bags miss my flight and we’re gonna be on the next flight that comes in two hours later regrettably my family was here to pick me up so I had to drive all the way home to drop them off then turn around and come back if I had waited on Alaska to deliver them they told me that they would be delivered in 4 to 6 hours after 8 AM tomorrow which would’ve caused the fish to spoil stink and be a lost cause they would’ve put about $2500 worth of fish down the drain very unhappy with Alaska Airlines for not getting my baggage here, especially since I had to pay for the extra service

Plenty of leg room, temperature was great and staff was excellent. Would do it more often.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

Older aircraft, no meal, only food was for purchase. Not impressed United.

United needs to step up their game. Delayed flight leaving Seattle, San Francisco. Older aircraft, not very comfortable.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Not pleasant trip cross country when the entertainment and WiFi system not working. No entertainment for entirety of route. Staff was rather nonchalant in that they dismissed the problem due to age of plane. It would have been nice to know this up front so I could have come prepared to read or download movies before boarding Coincidentally or not, there was a similar issue with the entertainment system on my previous flight I took on my fist leg of the trip. There are no seat TVs, so you must rely on the app when it works. United can do better. Also, what use it it to pay for boarding group 2 when half of the passengers are in the same line as you?

Plane boarded early a quickly, was mostly full. We left close to on time. And landed early.

My experience on this United Airlines flight was highly uncomfortable, primarily due to two issues: Cabin Temperature: The temperature on the Boeing 737 MAX 8 was unacceptably high, feeling consistently around 80 degrees throughout the flight. This made sleeping impossible and significantly detracted from the experience. Seating Arrangement: Being stuck in a middle seat for a six-and-a-half-hour overnight flight compounded the discomfort. Moving forward, I will always purchase a seat assignment to avoid this situation.

Premium Plus is a really good idea for longer flights

Everything you need to know for your flight to Caribbean

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