$336 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 8/31. 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.
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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 Cana1 stop$892
Santo Domingo
Santo Domingo2 stops$971
Nassau
Nassau1 stop$747
Saint Thomas Island
Saint Thomas Island2 stops$2,828
Kingston
Kingston2 stops$4,340
Punta Cana
Punta Cana1 stop$892
Santo Domingo
Santo Domingo2 stops$971
Nassau
Nassau1 stop$747
Saint Thomas Island
Saint Thomas Island2 stops$2,828
Kingston
Kingston2 stops$4,340

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

Fri, Dec 4 - Thu, Dec 10
United Airlines Logo
11:40 pm - 4:14 pm
ANC
-
NAS
12h 34m
1 stop
United Airlines Logo
2:55 pm - 10:39 pm
NAS
-
ANC
35h 44m
2 stops
$747United Airlines
Tue, Sep 1 - Fri, Sep 4
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
$777United Airlines
Tue, Aug 11 - Mon, Aug 17
American Airlines Logo
11:41 pm - 7:11 pm
ANC
-
NAS
15h 30m
2 stops
American Airlines Logo
7:45 am - 10:32 pm
NAS
-
ANC
18h 47m
2 stops
$802American Airlines
Tue, Sep 1 - Fri, Sep 4
Southwest Logo
11:55 pm - 10:00 pm
ANC
-
SJU
18h 05m
2 stops
Southwest Logo
6:00 am - 9:15 pm
SJU
-
ANC
19h 15m
2 stops
$810Southwest
Fri, Aug 21 - Sun, Aug 30
Southwest Logo
10:25 pm - 6:15 pm
ANC
-
SJU
15h 50m
2 stops
Southwest Logo
6:35 am - 10:45 pm
SJU
-
ANC
20h 10m
2 stops
$825Southwest
Tue, Aug 11 - Mon, Aug 17
American Airlines Logo
11:41 pm - 7:11 pm
ANC
-
NAS
15h 30m
2 stops
American Airlines Logo
7:45 am - 10:32 pm
NAS
-
ANC
18h 47m
2 stops
$842American Airlines
Wed, Aug 12 - Tue, Aug 25
Multiple Airlines Logo
11:21 pm - 12:30 pm
ANC
-
PUJ
33h 09m
1 stop
Multiple Airlines Logo
9:38 am - 1:38 am
PUJ
-
ANC
20h 00m
2 stops
$892Multiple Airlines
Wed, Sep 23 - Fri, Oct 2
Delta Logo
10:10 pm - 5:59 pm
ANC
-
STI
15h 49m
2 stops
Delta Logo
7:30 pm - 6:50 pm
STI
-
ANC
27h 20m
2 stops
$949Delta
Wed, Sep 23 - Fri, Oct 2
Delta Logo
10:10 pm - 5:59 pm
ANC
-
STI
15h 49m
2 stops
Delta Logo
7:30 pm - 6:50 pm
STI
-
ANC
27h 20m
2 stops
$969Delta
Wed, Dec 9 - Mon, Dec 14
Multiple Airlines Logo
1:27 am - 8:45 pm
ANC
-
NAS
15h 18m
2 stops
Multiple Airlines Logo
8:30 am - 12:10 am
NAS
-
ANC
19h 40m
2 stops
$1,057Multiple 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 $674, 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 February and May, when the average cost of round-trip tickets is $1,161 and $1,161 respectively.

Good to know

Low season

April

Cheapest flight

$336
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Anchorage to Santo Domingo

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 8471 reviews
8.1Boarding
7.8Entertainment
7.2Food
7.8Comfort
8.5Crew
Airline reviews

I missed the flight because the Minneapolis flight was 49 minutes LATE, and the Boise flight LEFT 24 minutes EARLY!

2.0 MediocreAnonymous, Jul 2026
MSP - BOI
Read more Delta reviews

I missed the flight because the Minneapolis flight was 49 minutes LATE, and the Boise flight LEFT 24 minutes EARLY!

Our flight was delayed multiple times and then canceled at almost 1 in the morning. We are a family of 7, traveling with 5 young children. When the flight we were supposed to fly on finally arrived after waiting all day after an international flight into JFK we were informed our flight was in need of a copilot and once they located one we would take off. Then our flight was cancelled because the copilot was over his hours and they couldn't locate another. They knew before taking off from the previous location that the copilot would be unable to fly. They could have communicated the cancellation of the flight hours in advance. Once they cancelled and the pilot and copilot got off the flight, they joked about it. While there are understandably limits on flight time for pilots, they can still handle the situation in a professional manner. The late cancellation resulted in angry passengers that required police intervention in the airport. It also occurred so late and included other delta flights that after trying 15 different hotels, we were unable to secure a hotel room, they were all booked. No rental cars were available in the area either. We ended up staying in the airport with the 5 children. We made it home after 54 hours of travel with maybe 2 hours of sleep. Our luggage was lost and had to be claimed at the airport at our final destination. This was the worst trip I have ever taken and the worst airport I have ever spent time in. I met two individuals in the airport that were kind and helpful; Tonya Maingot Williams from the can we hel desk that worked to help get us rebooked and home, as well as provide us with care bags for our extended stay in the airport. The other individual was Danielle from Buffalo Wild Wings that was so very kind when we found a place to take our family we were traveling with to eat, all 11 of us and we were able to sit down together to enjoy a meal during such a stressful time.

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

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

Comfortable seating POS to IAH. Food options were satisfactory. Good seat from IAH to ANC. Food options could be better.

The flight did not have its customary snacks during the flight. Apparently they were never loaded on the plane.

Flight was delayed 5 hours. Updates kept changing. Sears were extremely cramped. Very little leg room. Flight attendant was rushing through with drinks and hit me in the knee either the cart and didn’t apologize. They gave a 15 dollar voucher in airport which doesn’t buy. Much and it was so late that choices were limited.

I bought this ticket for my daughter. She had to pay for her carry on bag to be checked. My understanding is that transatlantic flights included carry on and personal item The nickeling and diming fo legacy carriers has stooped to an all time low. So sad.

Worst service- attendants dont want to help and sat us in front of bathroom

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

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.

Upgraded to first class. I would consider the first class on that plane to be only slightly more comfortable than coach. Long delay.

How is it that every American flight from DFW to IND is significantly delayed? This is the third time in two months I have been delayed flying out of DFW - ALWAYS for a maintenance issue. Makes me want to drop flying American altogether…or maybe flying through Dallas. Miserable experience.

Luggage took too long go get off plane in Knoxville. Was almost 45 minutes after the flight landed.

Initial flight had an engine overheat - returned to DFW. Had another plane ready, but crew timed out. Had to wait 5h for boarding. Fully boarded and pilot says plane is not flight worthy. Deplane and go to the other end of the terminal. Wait an hour to board third plane because the crew couldn’t leave the second plane because no wheelchairs were brought to remove passengers. Finally take off and there is no catering (in flight service) even in first class. Very much an AA failure.

We were delayed due to a mechanical issue, but the gate staff and then later captain were giving thorough and frequent updates. Ended up being delayed about an hour, but we did get out, so it was overall a good flight!

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.

Pros: "This was the worst flying experience I have ever encountered."
Cons: "We sat on the tarmac 3 hours, then deplaned to a holding area for another hour and then were told the flight would be delayed until 1 pm the next day. I booked this flight in order to arrive home 7 hours earlier than originally planned on Alaska Air. I finally arrived 20 hours LATER THAN I WOULD HAVE ARRIVED!"

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports