$463 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 7/31. 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

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

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 Cana3 stops$915
Santo Domingo
Santo Domingo2 stops$953
Nassau
Nassau2 stops$764
Kingston
Kingston2 stops$1,188
Puerto Plata
Puerto Plata2 stops$1,239
Punta Cana
Punta Cana3 stops$915
Santo Domingo
Santo Domingo2 stops$953
Nassau
Nassau2 stops$764
Kingston
Kingston2 stops$1,188
Puerto Plata
Puerto Plata2 stops$1,239

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

Mon, Aug 17 - Mon, Aug 24
Multiple Airlines Logo
1:29 am - 8:40 pm
ANC
-
NAS
15h 11m
2 stops
Multiple Airlines Logo
7:45 am - 9:36 am
NAS
-
ANC
29h 51m
2 stops
$764Multiple 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
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
Mon, Aug 24 - Thu, Aug 27
United Airlines Logo
11:09 pm - 2:44 pm
ANC
-
SJU
35h 35m
2 stops
United Airlines Logo
4:55 pm - 7:59 pm
SJU
-
ANC
31h 04m
2 stops
$818United Airlines
Mon, Aug 24 - Thu, Aug 27
United Airlines Logo
11:09 pm - 2:44 pm
ANC
-
SJU
35h 35m
2 stops
United Airlines Logo
3:56 pm - 7:59 pm
SJU
-
ANC
32h 03m
1 stop
$822United Airlines
Tue, Aug 25 - Sat, Sep 5
United Airlines Logo
3:15 pm - 1:45 pm
ANC
-
SJU
18h 30m
2 stops
United Airlines Logo
3:56 pm - 3:10 pm
SJU
-
ANC
27h 14m
2 stops
$828United Airlines
Wed, Jan 13 - Sat, Jan 23
Delta Logo
9:55 pm - 4:10 pm
ANC
-
SJU
13h 15m
1 stop
Delta Logo
7:30 am - 7:34 pm
SJU
-
ANC
17h 04m
1 stop
$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
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 August, when tickets cost $602 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $1,192 and $1,161 respectively.

Good to know

Low season

April

Cheapest flight

$463
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 10% increase in price.
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 8479 reviews
8.5Crew
7.8Comfort
7.8Entertainment
7.2Food
8.1Boarding
Airline reviews

This flight was originally delayed by ~45 minutes; which is fine. However, there were additional delays due to late offboarding of the prior flight, unclear issues with the boarding process, delays on the tarmac, and exceptionally long taxiing. None of these issues were communicated proactively. Additionally, the flight had exceptionally rough turbulence, which led to a very uncomfortable flight and no traditional beverage service. Again, this is understandable, but it was not communicated up-front by the flight team.

2.0 MediocreAidan, Jul 2026
RDU - BOS
Read more Delta reviews

This flight was originally delayed by ~45 minutes; which is fine. However, there were additional delays due to late offboarding of the prior flight, unclear issues with the boarding process, delays on the tarmac, and exceptionally long taxiing. None of these issues were communicated proactively. Additionally, the flight had exceptionally rough turbulence, which led to a very uncomfortable flight and no traditional beverage service. Again, this is understandable, but it was not communicated up-front by the flight team.

My flight was canceled, and instead of rebooking me on a non-stop first-class flight for the same day, which I originally had, Delta rebooked me on a one-stop flight for the following day. When I checked the Delta app, I noticed that there were available flights for both the same day and the next day. I believe this indicates poor management on their part.

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 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.

1. Everything was satisfactory concerning the flight. 2. Can't think of what could be better right now.

Onboard staff was courteous, helpful, responsive and friendly. The boarding process was disorganized, poorly communicated, and disheveled. Gate agents were yelling instead of using the PA system, didn’t communicate the timing delay of our flight, and created an atmosphere of chaos rather than order and communication. As far as I know, there was no reason for their. I would hate to see how it operated under extreme conditions. I’ve never seen United Airlines operations in such a state.

Baggage claim signs were not updated with my flight information, so I had to guess. The app wasn't updated either.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

Unbelievably smooth boarding at IAH and the flight attendants were top notch.

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.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

boarding announcements werent clear/loud. Tired of those cookies. Of the 3 staff/attendants, 1 was good and the other 2 were mediocre.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

American was the airline that Starlux contracted for this trip. I arrived in time to make the connecting flight on American, and then the baggage-handler debacle happened. For some reason, the first class and premium economy passengers' luggage was unloaded first. Never seen this happen before. They had handlers removing the bags from the carousel for those passengers. Meanwhile, all of the economy passengers were waiting for their bags, including me. And there were a lot of bags because it was an international flight packed full. While waiting for 45 minutes, my bag didn't show. Meanwhile, an American representative showed up asking if anyone has a connecting flight to Phoenix. Of course I spoke up, and they proceeded to try to find my bag because I had to take a bus to the actual terminal to catch my flight. Which I was not informed of before I arrived. After another 15 minutes of searching, my bag was finally found with the first-class passengers' bags because they had pulled it by mistake. So I rushed to the terminal with the American representative to catch my flight, and they informed me that I missed it and could not get another flight until the next day. Of course, after being on an international flight for 18 hours, I was in no mood to hear this. Now, to be fair, there were a few American employees who tried to help me. After hearing about the missed flight, they got a supervisor to talk to. I expressed my situation to the supervisor, and she was not helpful until I asked for compensation. She agreed to get me a hotel room for the night. So I agreed, and she disappeared into her office, and I waited. And waited. And waited. And waited. While waiting, I was asked by three different employees who knew of my situation if I had been helped. I told them I was waiting for the supervisor to get the hotel room, and they said they would check. Finally, after waiting for 75 minutes, one of the employees who had asked me if I had been helped arrived with my hotel room and arranged a ride to the hotel for me. Never saw the supervisor again. It was now 8 o'clock; I arrived at 5:45! My rebooked fight was scheduled for 6:11 this morning and I have now been informed it has been delayed until 10:00. So am I happy with American? NO I'M NOT!! ;

My flight was delayed by 8 hours I arrived at airport 4hrs earlier but to see if they can reroute me to get my connecting flt to Hong Kong. They auto rebooked my flt. With no chance. Which I missed this entire reservation through kayak. My next flt they got me on was at 6 am. Misses an entire day of my trip abroad all my accommodations seat assignments were missed and missed adding my TSA precheck to my ticket as well as my vegan meal request so I didnt have meals on any of the flight....so not a comfortable experience. Please help me with accommodations upon my return.

The boarding crew was very helpful with a little special problem I had. The inflight crew - so-so.

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

Information on your arrival and departure airports