$380 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 8/5. 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 Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Anchorage to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Anchorage to Caribbean Islands, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

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

Bundle and saveSave money when you bundle your flight + hotel.

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

Flight Deals
Booking Insights
Flight Deals

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$978
Santo Domingo
Santo Domingo2 stops$941
Nassau
Nassau1 stop$759
Saint Thomas Island
Saint Thomas Island2 stops$1,263
Kingston
Kingston2 stops$1,188
Puerto Plata
Puerto Plata2 stops$1,137
Punta Cana
Punta Cana1 stop$978
Santo Domingo
Santo Domingo2 stops$941
Nassau
Nassau1 stop$759
Saint Thomas Island
Saint Thomas Island2 stops$1,263
Kingston
Kingston2 stops$1,188
Puerto Plata
Puerto Plata2 stops$1,137

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

Tue, Jul 28 - Wed, Aug 5
United Airlines Logo
11:59 pm - 2:57 pm
ANC
-
NAS
10h 58m
1 stop
United Airlines Logo
2:53 pm - 11:10 am
NAS
-
ANC
24h 17m
2 stops
$759United Airlines
Sun, Aug 30 - Sat, Sep 5
Southwest Logo
10:25 pm - 10:50 pm
ANC
-
SJU
20h 25m
2 stops
Southwest Logo
5:55 am - 10:05 pm
SJU
-
ANC
20h 10m
2 stops
$790Southwest
Fri, Jul 31 - Fri, Aug 7
WestJet Logo
1:20 pm - 11:10 am
ANC
-
NAS
17h 50m
2 stops
WestJet Logo
12:00 pm - 12:30 pm
NAS
-
ANC
52h 30m
2 stops
$856WestJet
Tue, Jul 28 - Wed, Aug 5
American Airlines Logo
11:44 pm - 5:05 pm
ANC
-
NAS
13h 21m
2 stops
American Airlines Logo
10:20 am - 11:53 pm
NAS
-
ANC
17h 33m
2 stops
$868American Airlines
Thu, Jul 2 - Wed, Jul 8
American Airlines Logo
8:17 pm - 4:56 pm
ANC
-
NAS
16h 39m
1 stop
American Airlines Logo
3:00 pm - 10:39 pm
NAS
-
ANC
11h 39m
1 stop
$905American Airlines
Fri, Jul 31 - Fri, Aug 7
Multiple Airlines Logo
1:20 pm - 11:10 am
ANC
-
NAS
17h 50m
2 stops
Multiple Airlines Logo
12:00 pm - 1:38 pm
NAS
-
ANC
29h 38m
3 stops
$920Multiple Airlines
Tue, Aug 25 - Tue, Sep 8
Delta Logo
2:22 pm - 1:28 pm
ANC
-
SDQ
19h 06m
2 stops
Delta Logo
2:53 pm - 10:15 am
SDQ
-
ANC
23h 22m
2 stops
$941Delta
Tue, Dec 8 - Sat, Jan 9
Delta Logo
1:30 am - 1:35 am
ANC
-
SDQ
19h 05m
2 stops
Delta Logo
7:30 am - 1:45 am
SDQ
-
ANC
23h 15m
2 stops
$961Delta
Fri, Jul 31 - Fri, Aug 7
Multiple Airlines Logo
1:20 pm - 2:05 pm
ANC
-
PUJ
20h 45m
2 stops
Multiple Airlines Logo
3:00 pm - 1:38 pm
PUJ
-
ANC
26h 38m
3 stops
$1,150Multiple Airlines
Fri, Jul 31 - Fri, Aug 7
WestJet Logo
1:20 pm - 2:30 pm
ANC
-
KIN
22h 10m
2 stops
WestJet Logo
3:30 pm - 12:30 pm
KIN
-
ANC
48h 00m
2 stops
$1,242WestJet
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 $663, 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 seasonApril
Cheapest flight$380
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Anchorage to Nassau

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 8423 reviews
7.8Comfort
7.2Food
8.1Boarding
7.8Entertainment
8.5Crew
Airline reviews

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

4.0 OkayKelli, Jun 2026
ATL - TYS
Read more Delta reviews

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

We sat on the runway for over an hour before departure. That was unwelcome.

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

From checking to boarding, it was a seamless experience. The service agents were so helpful. The flight crew was so pleasant.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

Lost one piece of luggage even though I checked in 2.5 hours before the flight

It was Swiss. Our kosher meals were literally frozen solid and therefore inedible, and the crew didnt care.

For the expense of first class, the seats could have been nicer and higher tier snacks would have been nice.

The boarding process on the departure from LA was rather slow even though I was in Group 1. For first class, I was not expecting to have to pay for Wi-fi but I did and then the wi-fi was spotty. The entree was surprisingly good and so that was a pleasant surprise. However, once I got to Houston, it was terrible. Unfortunately there was bad weather but the constant gate changes for my connecting flight was difficult to manage due to having to navigate back and forth between different terminals.

We used Kayak to reserve our tickets and specifically checked the luggage option which was a more expensive option. When we arrived at the terminal we had to pay an extra $90 per suitcase for the three passengers. This has been a pattern for the past 3 years. Why charge for a more expensive luggage option, and the ticket price not include luggage?

They delayed the flight 3 hours because it wasn't full they moved us to 5 different gates probably the worst airline ever not even spirit is this bad.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Checking bag at terminal was horrible. No agents to check us in and only 1 kiosk working. Boarding went ok. Crew onboard was very scattered rained. Missed our row while serving and then didn’t see them hardly again.

Crew was amazing, takeoff wonderful. The bathroom was disgusting from before takeoff the odor made the flight uncomfortable as you could smell the bathroom from the center of the plane where we were sitting. Smelled like raw sewage. My daughter was throwing up as we landed due to the smell and horrible turbulence as we approached Newark.

Airline tickets are not cheap. You expect reliable competent service. Thanks to canceled flights and botched transfers we arrived at our destination two days late. This is not acceptable

I was not clear if food was offered or not.

Because I bought my ticket from Underpricer, I could not check in online. I could only check in at the airport and that was deeply frustrating because I had to arrive very early. The flight also departed 45 min late and passengers were given no explanations about why we were delayed. I was worried I would miss my connecting flight. Once on board, however, the flight was fine.

Absolutely terrible. They boarded the plane, supposedly realized they didn't refuel the plane or load the luggage so we sat as the gate inside the plane for over 2 hours while they supposedly did things that should have been done before having passengers board the planem

Flight cancelled. Twice. And no communication. No gate agent. Went past boarding time and had to go and see email from AA. Airport communication was bad

I love the e fact that the staff communicated swiftly when my flight was delayed and gate number changed

It was awful. The communication between corporate and the crew on the ground left more to be desired. The crew even said that Corporate was waiting on answers because they themselves didn't know. Every hour, there was a new excuse. I also understood that passengers were angry, but the crew should have done a better job at crowd control. There was a racial exchange between passengers that could've been avoided has the crew acted sooner.

Delayed and horrible communication and sat on flight for an hour before taking off

Flight was delayed three times and we had an international connecting flight which we would’ve missed but AA manage to find us a flight that allowed us to catch and we made our international flight. However, due to the flight change, I’m in Amman, Jordan missing all 4 bags. It’s been a nightmare. Been waiting since June 17 and today is June 20th. Still without luggage. Customer service wait times are two hours and I get disconnected while waiting. I’ll update when/if my luggage arrives. Every day is costing money in a hotel in Amman. I can’t continue my trip to Palestine until the luggage arrives. Then, I will be updating my review.

They did not offer coffee on a 7am flight…awful!!

Plane temperature was so hot that everyone on the plane was sweating. Departure gates changed 3 times in the hour before the flight. Internet service was so poor in the terminal that updates weren't always being received.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports