$297 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 1/31. 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

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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$926
Santo Domingo
Santo Domingo2 stops$881
Nassau
Nassau2 stops$598
Saint Thomas Island
Saint Thomas Island2 stops$1,115
Kingston
Kingston2 stops$1,605
Puerto Plata
Puerto Plata2 stops$1,291
Punta Cana
Punta Cana2 stops$926
Santo Domingo
Santo Domingo2 stops$881
Nassau
Nassau2 stops$598
Saint Thomas Island
Saint Thomas Island2 stops$1,115
Kingston
Kingston2 stops$1,605
Puerto Plata
Puerto Plata2 stops$1,291

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, Jan 24 - Sat, Jan 31
United Airlines Logo
9:00 am - 3:22 pm
ANC
-
NAS
26h 22m2 stops
United Airlines Logo
2:55 pm - 11:15 pm
NAS
-
ANC
12h 20m1 stop
$598United Airlines
Sun, Mar 8 - Sun, Mar 15
United Airlines Logo
9:10 pm - 3:22 pm
ANC
-
NAS
14h 12m1 stop
United Airlines Logo
3:35 pm - 8:01 pm
NAS
-
ANC
32h 26m1 stop
$720United Airlines
Mon, Jan 5 - Tue, Jan 13
Delta Logo
1:20 am - 11:59 pm
ANC
-
SJU
17h 39m2 stops
Delta Logo
3:20 pm - 12:48 am
SJU
-
ANC
14h 28m2 stops
$844Delta
Sat, Feb 7 - Mon, Feb 16
American Airlines Logo
12:38 am - 8:50 pm
ANC
-
SJU
15h 12m2 stops
American Airlines Logo
7:30 am - 11:04 pm
SJU
-
ANC
20h 34m2 stops
$884American Airlines
Mon, Jan 5 - Tue, Jan 13
Alaska Airlines Logo
1:25 am - 9:39 pm
ANC
-
SJU
15h 14m2 stops
Alaska Airlines Logo
7:07 am - 12:53 am
SJU
-
ANC
22h 46m3 stops
$895Alaska Airlines
Thu, Dec 25 - Sat, Jan 17
Delta Logo
1:44 pm - 11:56 am
ANC
-
SJU
17h 12m2 stops
Delta Logo
7:30 am - 7:01 pm
SJU
-
ANC
16h 31m1 stop
$934Delta
Sat, Feb 7 - Thu, Feb 12
Alaska Airlines Logo
12:38 am - 10:26 pm
ANC
-
SJU
16h 48m2 stops
Alaska Airlines Logo
6:00 am - 9:49 pm
SJU
-
ANC
20h 49m3 stops
$979Alaska Airlines
Mon, Jan 5 - Mon, Jan 12
Multiple Airlines Logo
8:30 pm - 3:42 pm
ANC
-
POP
14h 12m2 stops
Multiple Airlines Logo
4:42 pm - 11:56 am
POP
-
ANC
24h 14m2 stops
$1,291Multiple Airlines
Fri, Feb 13 - Wed, Feb 18
Multiple Airlines Logo
2:40 pm - 10:17 am
ANC
-
KIN
15h 37m2 stops
Multiple Airlines Logo
11:09 am - 10:19 am
KIN
-
ANC
27h 10m2 stops
$1,648Multiple Airlines
Thu, Jan 1 - Sat, Jan 17
American Airlines Logo
8:30 pm - 3:49 pm
ANC
-
SDQ
14h 19m2 stops
American Airlines Logo
6:00 am - 9:51 pm
SDQ
-
ANC
20h 51m3 stops
$2,663American 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.

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 $441 (return) on average. On the other hand, the most expensive months are March and May, when the average cost of round-trip tickets is $1,246 and $1,079 respectively.

What’s the cheapest day of the week to fly from Anchorage to Caribbean?

The average price of all round-trip flights from Anchorage to Caribbean clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Caribbean on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Thursday is the most expensive day to fly from Anchorage to Caribbean. For your return ticket, we recommend flying on a Monday and avoiding Fridays for the best deals.

Good to know

Low seasonAugust
Cheapest flight$297
Best time to beat the crowds with an average 56% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Anchorage to Santo Domingo

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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $1,008 on average. Morning departures are around 22% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $1,242.

Reviews of the top 4 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.
8.0
Alaska AirlinesOverall score based on 11427 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.1Food
7.0Entertainment
Airline reviews

The staff was friendly and the flight ran on time. Boarding was a zoo. This process could be greatly improved. They have done away with the entertainment they used to offer in favor a wifi signal for our phones and that wasn't working in half the flights. The beverage selection is poor and the quantity was minimal. I'm sure when the airlines can come up with something cheaper to serve than pretzels they they will switch to it. If their budget is that tight what else are they skimping on? (Maintenance, fuel, safety) Over all I'm underwhelmed!

4.0 OkayAnonymous, Dec 2025
FAI - SEA
Read more Alaska Airlines reviews

The staff was friendly and the flight ran on time. Boarding was a zoo. This process could be greatly improved. They have done away with the entertainment they used to offer in favor a wifi signal for our phones and that wasn't working in half the flights. The beverage selection is poor and the quantity was minimal. I'm sure when the airlines can come up with something cheaper to serve than pretzels they they will switch to it. If their budget is that tight what else are they skimping on? (Maintenance, fuel, safety) Over all I'm underwhelmed!

Flight was delayed several times then eventually cancelled which caused issues with our hotel, car rental and tickets to planned event. We also spent unplanned expense with Lyft to and from the airport which was frustrating. Customer care was not present during whole time at the airport.

My flight was canceled because of an IT outage, and they did not answer the phone for 8 hrs. There was no next flight out, I have missed my wedding because of this.

Liked the crew. Multiple delays. Altered my complete day and plans

The plane was clean. They got us to the destination. It was very difficult to hear the announcements at the gate. The person was speaking way too quickly, and the sound system did not carry to all parts of the seating area at the gate. The flight left more than an hour late, which left many of the passengers missing connections.

The chicken salad was very small, the lettuce was wilted and there was no flavor. The hamburger was excellent.

Mostly good. Delayed which in my experience so far happens often with Alaska Airlines. Thank you.

We received a check-in reminder the day before the flight, and it listed the flight at a later time. Correct flight number, same seats, etc. for 3 hours later. I called the airline to confirm and they had no record of the email. The info was wrong, and we would have missed our flight if we'd assumed it was correct. I want to know where/how we received this incorrect info.

My experience would’ve been great because we were on a new plane, but they said as we boarded that the plane would be too new to have WiFi, which to me is unreasonable - newer planes should def have WiFi! It was a 5 hour flight from Anchorage to San Fran and because there was no WiFi, I had to take an unexpected half day off work, which was super annoying because I had a lot to do and we only found out a few minutes before takeoff.

5 1/2 hour trip. Nice plane. easy boarding. Could have used a bit more beverage service but it was a red eye flight and they didn't want to wake everyone.

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Not great experience - we were super late boarding due to issues with aircraft. Then when we finally all got onboard and seated and they started taxiing out to the runway they just stopped then turned around and went back to the airport. Apparently the crew “ran out of time” to legally fly us. They mentioned that they were about 2 minutes away from taking off. I understand the rules and safety but kinda wonder why they would have bothered boarding us in the first place? Had to go all the way back and de plane and then wait in a HUGE line to get a hotel (this is somewhere around 2:30am) finally got to hotel by Uber (no shuttle after 20min so gave up) and they ended up putting us all back on the same aircraft at 10am next morning so got about 2.5 hours sleep. They did give us. $250 credit, but it was a São Paulo Brazil flight out of Dulles. The flight and everything was fine.

United overall experience is great these days. Airport experience was very organized. Staff on flight were great. App and information as good as it gets.

United have really come back. Airport and boarding process is clear and good, app and information also very good

They charged a fee for 1st bag checked. Others in same party were free.

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

I liked the humor of the captain and crew on the flight from Flagstaff to Dallas. They were humorous.

AA delayed the flight for 3 hours and 50 minutes, but delayed the last 2 hours, 30 minutes at a time, so if we knew before, could have stayed at home and worked instead of being at the airport wasting time... The plane's crew was excellent, not their fault.

After arriving in Dallas, the aircraft taxied for an unusually long time and was unable to park at the gate, which caused a significant delay and made me miss my connecting flight. I then had to wait in a very long line to be rebooked, and I was told that no hotel or meal accommodations would be provided. What is even more unacceptable is that my luggage was mishandled and has still not been located. My suitcase contains important medications that I urgently need, and I have been unable to access them due to the airline’s mishandling. This situation has caused me considerable stress and inconvenience, and I need this issue to be resolved immediately.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports