$391 Find Cheap Flights from Anchorage to Caribbean Islands - 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 Islands departing on 8/24. 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.
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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 Cana3 stops$915
Santo Domingo
Santo Domingo2 stops$973
Nassau
Nassau2 stops$707
Kingston
Kingston2 stops$1,188
Puerto Plata
Puerto Plata2 stops$1,239
Punta Cana
Punta Cana3 stops$915
Santo Domingo
Santo Domingo2 stops$973
Nassau
Nassau2 stops$707
Kingston
Kingston2 stops$1,188
Puerto Plata
Puerto Plata2 stops$1,239

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

Sat, Oct 31 - Fri, Nov 6
American Airlines Logo
9:22 pm - 10:16 pm
ANC
-
NAS
20h 54m
2 stops
American Airlines Logo
7:30 am - 7:09 pm
NAS
-
ANC
15h 39m
2 stops
$707American Airlines
Sat, Oct 31 - Sat, Nov 7
American Airlines Logo
9:22 pm - 10:16 pm
ANC
-
NAS
20h 54m
2 stops
American Airlines Logo
7:30 am - 7:09 pm
NAS
-
ANC
15h 39m
2 stops
$767American Airlines
Sat, Oct 31 - Sat, Nov 7
American Airlines Logo
9:22 pm - 2:43 pm
ANC
-
NAS
13h 21m
2 stops
American Airlines Logo
4:10 pm - 7:09 pm
NAS
-
ANC
30h 59m
1 stop
$793American Airlines
Fri, Oct 30 - Fri, Nov 6
United Airlines Logo
8:44 pm - 2:58 pm
ANC
-
NAS
14h 14m
1 stop
United Airlines Logo
2:40 pm - 7:15 pm
NAS
-
ANC
32h 35m
2 stops
$797United Airlines
Tue, Aug 25 - Sat, Sep 5
United Airlines Logo
9:20 pm - 11:50 pm
ANC
-
SJU
22h 30m
2 stops
United Airlines Logo
4:55 pm - 1:04 pm
SJU
-
ANC
24h 09m
2 stops
$812United Airlines
Tue, Aug 25 - Sun, Aug 30
United Airlines Logo
9:20 pm - 2:44 pm
ANC
-
SJU
13h 24m
1 stop
United Airlines Logo
1:00 am - 1:04 pm
SJU
-
ANC
16h 04m
2 stops
$815United Airlines
Wed, Jan 13 - Sun, Jan 24
Delta Logo
5:15 pm - 2:05 pm
ANC
-
SJU
15h 50m
2 stops
Delta Logo
6:15 am - 10:36 pm
SJU
-
ANC
21h 21m
2 stops
$835Delta
Fri, Jan 15 - Sat, Jan 23
Delta Logo
9:55 pm - 5:20 pm
ANC
-
SJU
14h 25m
2 stops
Delta Logo
7:30 am - 7:34 pm
SJU
-
ANC
17h 04m
1 stop
$855Delta
Mon, Aug 24 - Sun, Aug 30
Multiple Airlines Logo
2:28 am - 4:05 pm
ANC
-
PUJ
57h 37m
3 stops
Multiple Airlines Logo
11:46 am - 1:38 am
PUJ
-
ANC
41h 52m
3 stops
$915Multiple Airlines
Mon, Aug 24 - Sun, Aug 30
Multiple Airlines Logo
1:29 am - 7:54 pm
ANC
-
PUJ
38h 25m
2 stops
Multiple Airlines Logo
6:00 pm - 11:12 am
PUJ
-
ANC
21h 12m
1 stop
$985Multiple Airlines
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 $690, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Anchorage to Caribbean Islands, 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 Islands is April, when tickets cost $0 (return) on average. On the other hand, the most expensive months are July and December, when the average cost of round-trip tickets is $1,375 and $1,275 respectively.

Good to know

Low season

April

Cheapest flight

$391
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Anchorage to Punta Cana

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 3 airlines serving 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.
7.8
DeltaOverall score based on 8486 reviews
7.8Comfort
8.5Crew
8.1Boarding
7.8Entertainment
7.2Food
Airline reviews

Chaotic boarding at these gates, multiple gates squeezed in at the very end of a concourse, behind a restaurant. Agents gave up on boarding by individual zones. Flight itself was uneventful, which is all we hope for any more.

6.0 GoodAnonymous, Jul 2026
DTW - DCA
Read more Delta reviews

Chaotic boarding at these gates, multiple gates squeezed in at the very end of a concourse, behind a restaurant. Agents gave up on boarding by individual zones. Flight itself was uneventful, which is all we hope for any more.

Unprepared to rebook a flight of people. Uncommunicative. When I received updates in the app it was well after the announcement in the hold room. Offered a single $12 meal voucher, not enough for a sandwich at DEN, for a 17 hour delay. No one was able to explain their meal or hotel reimbursement policy for this cancellation, just handed a card to call the Help desk. My previous flight went through several delays and was finally cancelled, without explanation. The customer help desk closed while there was a long line. I then waited in line for a gate agent almost an hour while simultaneously on hold and trying to text with a remote Delta agent. Communicating with the text agent was almost impossible; they could not find any flights that got me back to my original city before the following evening. Kept offering itineraries that did not get me back to my origin airport or involved additional layovers. In 50 minutes on hold, never got through to an agent by phone. Finally spoke to one of the gate agents who was able to rebook on a red eye that had only one stop and got me back in the afternoon the next day, rather than late evening. Later by email, Delta offered 10,000 loyalty points for the inconvenience of the cancellation. The crew on the red eye flight were delightful. I don’t remember any food or entertainment on that flight.

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

The international portion was good. Food and beverage options were good. The sustainable wooden eatery was less than desirable. Your Star Alliance partner ANA provided real silverware. I'm 6'3" & 198 lbs and felt cramped in the exit row. How can that be? Flight attendant all had a pleasant disposition which is always good.

Flight was late to take off Plane broke down Had to move everyone to another plane Told we weren’t going to LGA but Newark Also told we would be taken to NY But United lied and we ended up at Newark at 2 in the morning Horrible experience. And the experience of trying to get compensation from United is just as bad. They could not care less about their passengers Never again!

Flight was late, the only reason I almost missed my flight was that my connection was also late.

Staff on the plane was incredible. Check-in was very complicated with no staff to help at the airport. I was charged for a second bag even though my ticket says 2 bags are free

Flight be on time would be a good start. Then train your flight attendants to be attentive and friendly. This time they completely forgot my row for the measly snack! United, do better!

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

Our flight gor canceled and there was no one to help us but told us to scan the qr code and fill the forms on-line. Very poor service especially we are tourists traveling to Washington DC for the 1st 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.

Patrons with larger bags were asked to check the bags when boarding. Seems like the most effective, and least costly way, way to successfully use the cramped space.

Like all planes recently, entertainment is achieved by giving the patron free WiFi and letting them stream shows via the screen on a phone or tablet.

Worst communication. Delayed boarding for two hours without a single announcement until hour 1 had passed - on time status showing until our flight was supposed to takeoff and the crew had already walked away. No one was boarding. Disgusting part of DFW overcrowded with no AC on a 97 degree day. Then the first app update is that we’d take off in 15 mins… but again no one had boarded a full flight. No announcement in the terminal so everyone is just crowded around a disgusting place with no info for over an hour which turned into two. This was an overfill flight and a disgrace to passenger decency all while likely just trying to fix their own issue of overbooking. The worst airline at the worst airport.

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

The flight was delayed almost three hours. I understand delays happen from time to time, but this flight was delayed no less than 10 times. I wish the amount of time of the delay was more accurate, versus delaying in 10 or 20 minute increments many, many times.

I thought American Airlines did well considering the adverse weather situation over July 21 and 22. I especially appreciated the consideration given to me when I got stuck in Miami on my way to Boston from Charleston, West Virginia. Thank you for providing a voucher for an overnight stay. Though it was only a few hours of sleep, it was very helpful. I was able to reschedule my medical appointment and got back to the Boston area on the 1st flight out of Miami as a standby passenger. It was very helpful that I was given number one priority on the standby list.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports