$331 Find Cheap Flights from Anchorage to Caribbean Islands

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 7/8. 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

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
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Flights Deals

Best Caribbean Islands Flight Deals from Anchorage

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$931
Santo Domingo
Santo Domingo3 stops$782
Nassau
Nassau2 stops$737
Saint Thomas Island
Saint Thomas Island2 stops$1,194
Kingston
Kingston3 stops$921
Puerto Plata
Puerto Plata2 stops$1,446
Punta Cana
Punta Cana2 stops$931
Santo Domingo
Santo Domingo3 stops$782
Nassau
Nassau2 stops$737
Saint Thomas Island
Saint Thomas Island2 stops$1,194
Kingston
Kingston3 stops$921
Puerto Plata
Puerto Plata2 stops$1,446

Cheap Flights from Anchorage to Caribbean Islands

 
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

Wed, Jul 9 - Fri, Jul 25
 Logo
1:20 pm - 1:35 amANC-SJU
32h 15m3 stops
 Logo
11:59 pm - 7:48 pmSJU-ANC
23h 49m3 stops
Wed, Jul 9 - Fri, Jul 25
 Logo
1:20 pm - 1:35 amANC-SJU
32h 15m3 stops
 Logo
11:59 pm - 7:48 pmSJU-ANC
23h 49m2 stops
Sun, Sep 14 - Sun, Sep 21
Air Canada Logo
4:45 pm - 5:30 pmANC-NAS
20h 45m2 stops
Air Canada Logo
6:30 pm - 3:56 pmNAS-ANC
25h 26m2 stops
$737Air Canada
Find Deal
Wed, Jul 30 - Wed, Aug 6
United Airlines Logo
8:16 pm - 1:31 pmANC-NAS
13h 15m1 stop
United Airlines Logo
5:00 pm - 10:52 pmNAS-ANC
33h 52m2 stops
$743United Airlines
Find Deal
Sat, Aug 30 - Sun, Sep 7
Delta Logo
12:42 am - 10:07 pmANC-SJU
17h 25m2 stops
Delta Logo
7:30 am - 11:27 pmSJU-ANC
19h 57m2 stops
$804Delta
Find Deal
Wed, Jul 30 - Wed, Aug 6
United Airlines Logo
8:16 pm - 1:31 pmANC-NAS
13h 15m1 stop
United Airlines Logo
5:00 pm - 7:24 pmNAS-ANC
30h 24m1 stop
$810United Airlines
Find Deal
Sun, Dec 7 - Sat, Dec 27
Delta Logo
9:55 pm - 5:10 pmANC-SJU
14h 15m2 stops
Delta Logo
4:42 pm - 12:59 amSJU-ANC
13h 17m1 stop
$859Delta
Find Deal
Fri, Aug 8 - Mon, Aug 11
Air Canada Logo
4:40 pm - 3:20 pmANC-PUJ
42h 40m2 stops
Air Canada Logo
4:25 pm - 3:47 pmPUJ-ANC
27h 22m2 stops
$931Air Canada
Find Deal
Mon, Jun 30 - Sat, Jul 5
Alaska Airlines Logo
1:44 am - 2:01 pmANC-SJU
32h 17m2 stops
Alaska Airlines Logo
3:23 pm - 4:37 amSJU-ANC
17h 14m1 stop
$1,334Alaska Airlines
Find Deal
Tue, Jul 8 - Thu, Jul 24
Alaska Airlines Logo
1:44 am - 5:06 amANC-SJU
23h 22m2 stops
Alaska Airlines Logo
12:59 am - 12:56 pmSJU-ANC
39h 57m2 stops
$1,464Alaska Airlines
Find Deal
Useful Info

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 $941, 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 $782 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $1,292 and $1,171 respectively.

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

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

When flying from Anchorage to Caribbean Islands, you should consider leaving on a Tuesday and avoid Thursdays if you are looking for the best rates. For your return to Anchorage, you’ll find the best rates on Mondays and the most expensive ones on Fridays.


Good to know

Low seasonAugust
High seasonDecember
Cheapest flight$331
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Anchorage to San Juan

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.

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

    The cheapest time of day to fly to Caribbean Islands 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 Islands 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 airlines flying 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.
8.0
Alaska AirlinesOverall score based on 10000 reviews
7.1Food
7.8Comfort
8.5Crew
8.1Boarding
7.1Entertainment
Airline reviews

The flight was short and smooth. The crew was friendly and courteous.

10.0 ExcellentAnnette, Jun 2025ANC - SEA
Read more Alaska Airlines reviews

The flight was short and smooth. The crew was friendly and courteous.

It sucks, flight delays at FAT caused us to miss a day at lodge and overnight in Seattle. Flight delays coming home also. Never again

Like the friendliness of the crew, each flight had a very very drunk person next to me and the last flight had a very obese man pushing me into the aisle while the crew kept ending up hitting me in the shoulder with the beverage carts.

Booked a first class ticket from Anchorage to Seattle but was denied complimentary access to Alaska Lounge as our 1500 mile flight wasn’t long enough’

It was very good. I love flying with Alaska air.

Flying sucks these days. No airline is better than another. Alaska Air At least gives you some pretzel snacks. That is about all I can say for it.

Boarding for Alaska Airlines is always chaotic with many people crowding the gates. Arriving in on Alaska in Los Angeles is always interesting since there is never a gate available. So the planes are often parked all the way out on the west side of the airport while waiting for the gate to be cleared of the departing plane. This flight was no exception.

The would have rated higher, but I asked for a cup of coffee twice and never got one. Later found the crew sitting in the back having a meal and visiting. Just saying.

The flight was delayed almost an hour causing many passengers to be at jeopardy of missing their connecting flights. There was no help in providing passengers help with connections or allowing passengers with connecting flights to exit the plane in an expediated manner.

This was our fist time flying Alaska Airlines. Overall it was a great experience. Ticket counter, gate agents and flight attendants were all wonderful. They all seemed happy at what they do and it shows. Of 4 legs, the onboard WiFi was spotty on 1 leg. The food in first class cabin was ok. Couldn’t get the text messaging notifications to work so had to rely on Flight Aware and the Alaska App. Flights were on time and uneventful. We would def fly Alaska Airlines again :)

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Overall, aside from the baggage issue, it was as good as one expects.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

I want to single out flight attendant Mitch who was in the Premium Economy section. When my wife’s hearing aide dropped through the cushion under the seat he was able to locate it and return it to her. Food was a different matter. Dinner was fine. Breakfast was another matter. They had a yogurt dish that the ran out of and the alternative was not very good according to those we talked to.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Flight was delayed long enough that I was misding my connecting flight. The agents could not get me on a comparable flight, nor could they get me s Main Cabin seat I had paid for, nor could they get me on a comparable connecting flight. The gate agent would not issue meal vouchers, even though I was delayed over six hours! I had to spend over an hour and 15 minutes with customer service on the phone to See if they could get me on a better flight and get a meal voucher. Customer service was not helpful enough in trying to find alternate flights and it Ended up taking me 24 hours for a 12 hour trip!! Delta does not provide upgrades NOR will they even give you a pass for a few hours to their lounge. They claim that they do not issue daily passes to their lounge anymore. I call BS since this would be no extra cost to them to provide excellent customer service and give you a few hours to relax in comfort when you’re sitting in a crowded airport and your flight has been screwed up for that many hours.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Everything you need to know for your flight to Caribbean Islands

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