$315 Find Cheap Flights from Anchorage to Caribbean - Compare and Save

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 7/21. 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, 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$969
Santo Domingo
Santo Domingo2 stops$951
Nassau
Nassau2 stops$747
Kingston
Kingston2 stops$1,295
Puerto Plata
Puerto Plata2 stops$1,399
Punta Cana
Punta Cana2 stops$969
Santo Domingo
Santo Domingo2 stops$951
Nassau
Nassau2 stops$747
Kingston
Kingston2 stops$1,295
Puerto Plata
Puerto Plata2 stops$1,399

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

Thu, Aug 6 - Thu, Aug 13
American Airlines Logo
11:41 pm - 7:11 pm
ANC
-
NAS
15h 30m
2 stops
American Airlines Logo
10:20 am - 11:53 pm
NAS
-
ANC
17h 33m
2 stops
$747American Airlines
Sat, Sep 5 - Sat, Sep 12
Multiple Airlines Logo
2:28 am - 7:15 pm
ANC
-
NAS
12h 47m
2 stops
Multiple Airlines Logo
7:45 am - 1:38 am
NAS
-
ANC
21h 53m
2 stops
$774Multiple Airlines
Tue, Dec 1 - Tue, Dec 8
United Airlines Logo
11:40 pm - 11:53 am
ANC
-
NAS
32h 13m
2 stops
United Airlines Logo
2:55 pm - 10:39 pm
NAS
-
ANC
35h 44m
2 stops
$790United Airlines
Sun, Aug 30 - Sat, Sep 5
United Airlines Logo
8:00 pm - 1:45 pm
ANC
-
SJU
37h 45m
2 stops
United Airlines Logo
3:56 pm - 3:10 pm
SJU
-
ANC
27h 14m
2 stops
$791United Airlines
Mon, Aug 24 - Fri, Aug 28
United Airlines Logo
9:20 pm - 1:45 pm
ANC
-
SJU
36h 25m
2 stops
United Airlines Logo
3:56 pm - 7:59 pm
SJU
-
ANC
32h 03m
1 stop
$800United Airlines
Mon, Aug 24 - Fri, Aug 28
United Airlines Logo
9:20 pm - 1:45 pm
ANC
-
SJU
36h 25m
2 stops
United Airlines Logo
3:56 pm - 7:35 pm
SJU
-
ANC
31h 39m
2 stops
$806United Airlines
Tue, Sep 1 - Tue, Sep 15
Delta Logo
12:54 pm - 1:28 pm
ANC
-
SDQ
20h 34m
2 stops
Delta Logo
7:35 pm - 9:00 pm
SDQ
-
ANC
29h 25m
2 stops
$951Delta
Sat, Aug 29 - Sat, Sep 5
JetBlue Logo
8:19 pm - 12:57 pm
ANC
-
STI
12h 38m
1 stop
JetBlue Logo
6:00 am - 7:11 pm
STI
-
ANC
17h 11m
1 stop
$994JetBlue
Sat, Dec 12 - Tue, Dec 22
Delta Logo
1:10 pm - 1:30 pm
ANC
-
PUJ
19h 20m
2 stops
Delta Logo
1:55 pm - 12:53 am
PUJ
-
ANC
15h 58m
2 stops
$1,013Delta
Mon, Oct 5 - Thu, Oct 8
Air Canada Logo
8:59 pm - 1:55 pm
ANC
-
KIN
37h 56m
2 stops
Air Canada Logo
3:05 pm - 7:57 pm
KIN
-
ANC
31h 52m
2 stops
$1,424Air Canada
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 February, when tickets cost $226 (return) on average. On the other hand, the most expensive months are January and June, when the average cost of round-trip tickets is $1,020 and $1,015 respectively.

Good to know

Low seasonApril
Cheapest flight$315
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Anchorage to San Juan

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.

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.
7.8
DeltaOverall score based on 8451 reviews
8.1Boarding
7.8Comfort
7.8Entertainment
8.5Crew
7.2Food
Airline reviews

It was as good as it could be. Flying is not a pleasant experience these days.

8.0 ExcellentMark, Jun 2026
LAX - ORD
Read more Delta reviews

It was as good as it could be. Flying is not a pleasant experience these days.

The plane was old and thus the seats were not good. No cushion left whatsoever, and it all was a bit worn out.

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.

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

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

Food from the flight from Atlanta to Santiago was very poor..

Delta was great the entertainment was outdated. Screen was very small and didn’t work.

The boarding was great. With all the delays I was grateful to get on the plane and headed for home. There was no in flight entertainment. Seats were very uncomfortable! Unfortunately we were seated next to an exit row so there was no recline in our seat. Other than that it was a smooth ride.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

Delta is one of the best airlines I have flown

I was very disappointed with my experience at the United Airlines baggage check. The representative was rude and unhelpful. I was required to remove approximately 1.5 pounds from my two checked bags, even though it was a very small amount over the limit. The interaction was unnecessarily unpleasant, and I expected much better customer service. I hope United will review this incident and provide additional customer service training to its staff.

No extra snacks were available. Meals quality is terrible. Crew was not friendly.

I was exhausted from a long day. The flight was smooth. The first flight during my 3 week travel that took off on time.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

I needed internet for critical matters and it never worked.

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

There was no food available for this red eye... one little waffle cookie for a 6+ hour flight... thank God I was able to sleep some

To san Francisco it was ok. From sf to Manila it was horrible

You have got to come up with a better way of getting connecting flight people off the plane first. Flying doesn’t bring out the best in people but exiting off a plane rules needs to come from management, not from the expectation that passengers will be “kind” and let them off first. Perhaps exiting in zones? Like boarding? Zone 1 exits are connecting people. This frustration led to many people missing their flights or scrambling. We were delayed leaving the first leg which amplified this.

My flight was delayed twice. The first time because of “plane maintenance” and the second because the previous flight who supposedly “arrived early” took an obnoxiously long time to get off the plane. Total delay was over an hour for no reason. Not to mention your airline repeatedly changed our gate from one end of the terminal to the other. Not very happy about this experience. My previous flights with American haven’t had this many issues.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

We’ve had a year of delays with American, and this one was another flight to add to that list. It just reduced our vacation by a day! So frustrating. In-flight entertainment (TVs) weren’t working, There was no drinks service due to delivery issues.

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

2 hours delay on my flight causing me to miss my connecting flight. Cause was for maintenance. I understand maintenance is important but maintenance should be done before boarding people!

I take this flight about 6-8 times per year. It is convenient and saves an hour or two by skipping PDX, SEA, PHX, or ORD (but it takes longer to get bags to the carousel than Alaska Airlines). I wish the food service were better (but they might cut back on it because it is a red-eye). The WifI seems to go down about an hour out of Anchorage, and then comes back about an hour later...so be warned if this is an issue for you.

Flight was good. However, they had everyone board the plane then made us sit there on the tarmac for an hour plus due to maintenance issues. Besides that flight attendant and pilot were amazing.

Check in agent was helpful and nice. Flight was OK. Our flight in Chicago was delayed 8 hours without an explination. This was our journey home. After a horrible flight experience on on the way to our vacation where our plane was diverted for an emergency medical issue, was grounded for hours, we missed our connecting flight by 25 minutes, and it took a day yo get re-booked, this was yet another bad experience that American seemed unwilling to help out with, much less compensate us for the

Entertainment was very plentiful, staff were courteous. Seating was HORRIBLE. That is the most cramped I’ve ever been on any flight …Jet Blue and Spirit included. Very uncomfortable for a six hour trip.

Pros: "This was the worst flying experience I have ever encountered."
Cons: "We sat on the tarmac 3 hours, then deplaned to a holding area for another hour and then were told the flight would be delayed until 1 pm the next day. I booked this flight in order to arrive home 7 hours earlier than originally planned on Alaska Air. I finally arrived 20 hours LATER THAN I WOULD HAVE ARRIVED!"

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports