$318 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 6/10. 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, 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$1,028
Santo Domingo
Santo Domingo1 stop$943
Nassau
Nassau1 stop$849
Kingston
Kingston2 stops$1,326
Puerto Plata
Puerto Plata2 stops$1,123
Punta Cana
Punta Cana2 stops$1,028
Santo Domingo
Santo Domingo1 stop$943
Nassau
Nassau1 stop$849
Kingston
Kingston2 stops$1,326
Puerto Plata
Puerto Plata2 stops$1,123

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

Tue, Aug 11 - Sun, Sep 13
Southwest Logo
11:15 pm - 6:10 pm
ANC
-
SJU
14h 55m
2 stops
Southwest Logo
5:30 am - 11:45 pm
SJU
-
ANC
22h 15m
2 stops
$790Southwest
Wed, Jul 1 - Wed, Aug 12
Delta Logo
2:12 pm - 12:54 pm
ANC
-
SJU
18h 42m
2 stops
Delta Logo
7:30 am - 11:34 pm
SJU
-
ANC
20h 04m
2 stops
$815Delta
Fri, May 15 - Sat, May 23
United Airlines Logo
11:49 pm - 4:10 pm
ANC
-
NAS
12h 21m
1 stop
United Airlines Logo
4:58 pm - 11:10 am
NAS
-
ANC
22h 12m
2 stops
$849United Airlines
Fri, May 15 - Sat, May 23
United Airlines Logo
11:49 pm - 4:10 pm
ANC
-
NAS
12h 21m
1 stop
United Airlines Logo
3:10 pm - 11:10 am
NAS
-
ANC
24h 00m
1 stop
$868United Airlines
Tue, Aug 11 - Sun, Sep 13
American Airlines Logo
9:55 pm - 2:10 pm
ANC
-
SJU
12h 15m
1 stop
American Airlines Logo
7:05 pm - 7:08 pm
SJU
-
ANC
28h 03m
2 stops
$919American Airlines
Sat, Jun 6 - Fri, Jun 26
American Airlines Logo
9:53 pm - 11:56 pm
ANC
-
SJU
22h 03m
1 stop
American Airlines Logo
6:00 am - 8:41 pm
SJU
-
ANC
18h 41m
2 stops
$930American Airlines
Mon, Oct 5 - Fri, Oct 9
Air Canada Logo
8:55 pm - 1:55 pm
ANC
-
KIN
38h 00m
2 stops
Air Canada Logo
3:05 pm - 7:45 pm
KIN
-
ANC
31h 40m
2 stops
$1,326Air Canada
Mon, Oct 5 - Fri, Oct 9
Air Canada Logo
8:55 pm - 1:55 pm
ANC
-
KIN
38h 00m
2 stops
Air Canada Logo
3:05 pm - 7:45 pm
KIN
-
ANC
31h 40m
2 stops
$1,447Air Canada
Fri, May 15 - Sat, May 23
Multiple Airlines Logo
2:40 pm - 4:15 pm
ANC
-
NAS
21h 35m
3 stops
Multiple Airlines Logo
6:30 pm - 1:36 pm
NAS
-
ANC
23h 06m
2 stops
$1,473Multiple Airlines
Fri, Jul 17 - Fri, Aug 14
Multiple Airlines Logo
8:52 pm - 4:48 pm
ANC
-
SDQ
15h 56m
2 stops
Multiple Airlines Logo
6:50 pm - 7:48 pm
SDQ
-
ANC
28h 58m
3 stops
$1,839Multiple Airlines
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.

Which airlines provide the cheapest flights from Anchorage to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Anchorage to Caribbean were found on United Airlines ($729) and Southwest ($790).

Good to know

Low seasonApril
Cheapest flight$318
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 10% 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 airlines flying 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.
7.9
DeltaOverall score based on 8434 reviews
7.8Entertainment
7.2Food
7.9Comfort
8.1Boarding
8.5Crew
Airline reviews

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

6.0 GoodAkanksha Devidas, Apr 2026
BOS - JFK
Read more Delta reviews

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

Putting people that close to the bathroom, where you have to look into the bathroom as people are exiting and entering was not great and the smell was also not great. I know the airlines are desperate for more chairs, but that seat is a crime.

My bags were misplaced!!! Im in a foreign country with no bags

The entertainment options on the seat back video boards were nice.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

Due to cancellation of connecting flight (Lufthansa) I didn’t fly with United

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports