$334 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

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

Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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$885
Santo Domingo
Santo Domingo1 stop$943
Nassau
Nassau2 stops$708
Kingston
Kingston2 stops$1,195
Puerto Plata
Puerto Plata2 stops$1,123
Punta Cana
Punta Cana2 stops$885
Santo Domingo
Santo Domingo1 stop$943
Nassau
Nassau2 stops$708
Kingston
Kingston2 stops$1,195
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

Sat, Jun 6 - Sat, Jun 13
Air Canada Logo
2:40 pm - 5:30 pm
ANC
-
NAS
22h 50m
2 stops
Air Canada Logo
6:30 pm - 1:36 pm
NAS
-
ANC
23h 06m
2 stops
$708Air Canada
Sun, May 17 - Sun, May 24
United Airlines Logo
8:45 pm - 2:57 pm
ANC
-
NAS
14h 12m
1 stop
United Airlines Logo
3:59 pm - 11:10 am
NAS
-
ANC
23h 11m
2 stops
$780United Airlines
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
Sat, Jun 6 - Sat, Jun 13
Multiple Airlines Logo
1:22 pm - 7:15 pm
ANC
-
NAS
25h 53m
3 stops
Multiple Airlines Logo
6:30 pm - 1:36 pm
NAS
-
ANC
23h 06m
2 stops
$830Multiple Airlines
Sun, May 17 - Sun, May 24
Southwest Logo
11:55 pm - 11:40 pm
ANC
-
SJU
19h 45m
2 stops
Southwest Logo
5:45 am - 10:45 pm
SJU
-
ANC
21h 00m
2 stops
$835Southwest
Wed, Jul 1 - Wed, Aug 12
Delta Logo
8:10 pm - 11:44 am
ANC
-
SJU
11h 34m
1 stop
Delta Logo
7:30 am - 12:33 am
SJU
-
ANC
21h 03m
2 stops
$855Delta
Fri, Jun 5 - Fri, Jun 26
Multiple Airlines Logo
1:22 pm - 10:42 pm
ANC
-
SJU
29h 20m
2 stops
Multiple Airlines Logo
2:11 am - 7:48 pm
SJU
-
ANC
21h 37m
2 stops
$901Multiple 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
Sun, May 17 - Sun, May 24
American Airlines Logo
8:30 pm - 4:34 pm
ANC
-
NAS
16h 04m
2 stops
American Airlines Logo
11:03 am - 8:47 pm
NAS
-
ANC
13h 44m
2 stops
$954American 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 ($780) 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 8450 reviews
7.2Food
8.1Boarding
8.5Crew
7.8Entertainment
7.9Comfort
Airline reviews

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

2.0 MediocreNicholas, Apr 2026
LGA - CLT
Read more Delta reviews

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

Everything was great. The only issue is unfixable. Seats are too small. 😁🤪

This wasn't my experience with Delta. It was just the Pegasus flight. Seats were very hard. Staff was kinda rough. Not very nice. Charged me for snacks. For a 4 hour flight I would've expected more.

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

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.

United Airline crews were very friendly and very attentive. 12 hours flight was gone like in a shorter one.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

Food was surprisingly delicious. Space in the seat is horrible when the seating front is reclined. Movie offerings were terrible. Crew was friendly and helpful.

They told us yesterday APR21st that they were cleaning the plane and we got delayed. After that they said they didn't had any crew for the flight so they cancelled the flight till next day.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Flight itself excellent, but delayed so missed connection & got to destination 2 hrs later

The flight crew on this leg of my trip was very friendly and pleasant. Every one of them was humorous, as well as helpful and accommodating. This group was BY FAR the best crew I’ve flown with. They deserve kudos.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was delayed from take off because only one runway was operational in San Francisco.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports