$304 Find Cheap Flights from Anchorage to Caribbean Islands

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 Islands departing on 3/1. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Anchorage to Caribbean Islands, 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 Anchorage to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Anchorage to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$947
Santo Domingo
Santo Domingo2 stops$912
Nassau
Nassau1 stop$849
Kingston
Kingston2 stops$1,489
Puerto Plata
Puerto Plata2 stops$952
Punta Cana
Punta Cana1 stop$947
Santo Domingo
Santo Domingo2 stops$912
Nassau
Nassau1 stop$849
Kingston
Kingston2 stops$1,489
Puerto Plata
Puerto Plata2 stops$952

Book Cheap Anchorage to Caribbean Islands 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 Islands 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 Islands

ج, مايو 29 - ر, يونيو 10
Sun Country Air Logo
1:18 pm - 3:07 pm
ANC
-
SJU
21h 49m
1 stop
Sun Country Air Logo
4:20 pm - 12:18 pm
SJU
-
ANC
23h 58m
1 stop
$646Sun Country Air
ج, مايو 29 - س, يونيو 13
Sun Country Air Logo
1:18 pm - 3:07 pm
ANC
-
SJU
21h 49m
1 stop
Sun Country Air Logo
4:20 pm - 12:18 pm
SJU
-
ANC
23h 58m
1 stop
$671Sun Country Air
ث, يونيو 2 - خ, يونيو 11
Delta Logo
8:30 pm - 1:18 pm
ANC
-
SJU
12h 48m
1 stop
Delta Logo
2:35 pm - 1:35 am
SJU
-
ANC
15h 00m
2 stops
$765Delta
ث, يونيو 2 - ح, يونيو 14
Delta Logo
5:15 pm - 1:19 pm
ANC
-
SJU
16h 04m
2 stops
Delta Logo
2:35 pm - 1:35 am
SJU
-
ANC
15h 00m
2 stops
$785Delta
ن, مايو 4 - ر, مايو 6
United Airlines Logo
11:49 pm - 9:24 pm
ANC
-
SJU
17h 35m
2 stops
United Airlines Logo
4:55 pm - 5:01 pm
SJU
-
ANC
28h 06m
2 stops
$794United Airlines
ن, مايو 4 - ر, مايو 6
United Airlines Logo
9:00 pm - 8:34 pm
ANC
-
SJU
19h 34m
1 stop
United Airlines Logo
4:55 pm - 5:01 pm
SJU
-
ANC
28h 06m
2 stops
$802United Airlines
خ, مارس 26 - خ, أبريل 2
American Airlines Logo
8:13 pm - 2:32 pm
ANC
-
NAS
14h 19m
1 stop
American Airlines Logo
12:48 pm - 12:39 am
NAS
-
ANC
15h 51m
2 stops
$849American Airlines
خ, مارس 26 - خ, أبريل 2
American Airlines Logo
8:13 pm - 4:54 pm
ANC
-
NAS
16h 41m
2 stops
American Airlines Logo
12:48 pm - 12:39 am
NAS
-
ANC
15h 51m
2 stops
$894American Airlines
ن, مارس 30 - ر, أبريل 1
Air Canada Logo
9:04 pm - 12:25 pm
ANC
-
NAS
35h 21m
2 stops
Air Canada Logo
9:10 pm - 7:55 pm
NAS
-
ANC
26h 45m
2 stops
$1,028Air Canada
ح, مارس 29 - خ, أبريل 2
Air Canada Logo
9:04 pm - 12:35 pm
ANC
-
KIN
36h 31m
2 stops
Air Canada Logo
1:55 pm - 7:55 pm
KIN
-
ANC
33h 00m
2 stops
$1,489Air Canada
Booking Insights

KAYAK's insights & trends for Anchorage to Caribbean Islands flights

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

Can I save money by flying with a layover from Anchorage to Caribbean Islands?

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 $645, prices are generally cheapest when you fly direct.

Good to know

Low seasonAugust
Cheapest flight$304
Best time to beat the crowds with an average 49% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Anchorage to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

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

    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 Islands 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 Islands?

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

Reviews of the top airline flying from Anchorage to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Anchorage to Caribbean Islands. 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 Anchorage to Caribbean Islands? 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.
7.9
DeltaOverall score based on 8178 reviews
8.5Crew
7.2Food
8.1Boarding
7.8Entertainment
7.9Comfort
Airline reviews

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

2.0 MediocreMichael, Feb 2026
ORD - LGA
Read more Delta reviews

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

No wheel chair as requested at Atlanta arrival on first flight.

Only freetext wifi was available in flight; browsing WiFi required payment. Since the seats had no in flight entertainment, Delta should revisit this policy on this longer flight.

Only water, tea or coffee served midflight, even to comfort seating. Man next to me needed two seats and took up a portion of my seat and Delta did nothing.

The flight was great as well as the airline staff

First class and monitors weren’t working for mine & my husbands. Eventually fixed, but quite annoyed as we bought first class. Also, No foot rests.

Prior to takeoff, the pilot told us there was a possibility of not being able to land and going to Portland. Well that happened, we took off and then did 8 loops around Spokane before the pilot told us we ran out of fuel and had to go to Portland. So for a 35 minute flight we have now been on the plane for 3 hours (boarded at 6:50 am and landed in Portland at 10:30). Then, we just sat in Portland's airport with no updates of when we can start heading back. All of a sudden, our pilots and crew just left, leaving us stranded in a different city and state. We continued to sit in Portland until we finally got a new crew assigned and boarded the plane (This was from 10:30-2). We then sat on the plane for an additional hour before take off because they had to count us multiple times. We finally landed in Spokane at 3:55 PM. So a flight that should have taken at max an hour took us 10 hours and we missed the majority of the recruiting event we went for.

It was delayed but other than that it was great.

Got on the plane and sat there for an hour before departure.

Second flight in a row where the entertainment system is broken. 5 hour long flight with no entertainment and flight attendants did not seem interested in resolving the matter. Very shocked to be treated this poorly considering I paid for a first class experience and have Diamond Medallion status.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports