$322 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 10/16. 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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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 Cana2 stops$924
Santo Domingo
Santo Domingo2 stops$888
Nassau
Nassau2 stops$802
Kingston
Kingston2 stops$1,094
Puerto Plata
Puerto Plata2 stops$953
Punta Cana
Punta Cana2 stops$924
Santo Domingo
Santo Domingo2 stops$888
Nassau
Nassau2 stops$802
Kingston
Kingston2 stops$1,094
Puerto Plata
Puerto Plata2 stops$953

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, Feb 3 - Fri, Feb 13
Delta Logo
12:40 am - 8:30 pmANC-SJU
14h 50m2 stops
Delta Logo
4:25 pm - 12:59 amSJU-ANC
13h 34m1 stop
$744Delta
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Sat, Jan 10 - Mon, Jan 19
Delta Logo
12:40 am - 11:58 pmANC-SJU
18h 18m2 stops
Delta Logo
7:00 am - 12:28 amSJU-ANC
22h 28m2 stops
$764Delta
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Wed, Oct 8 - Sun, Oct 12
American Airlines Logo
7:52 pm - 8:50 pmANC-NAS
20h 58m2 stops
American Airlines Logo
7:45 am - 6:44 pmNAS-ANC
14h 59m2 stops
$802American Airlines
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Thu, Oct 23 - Thu, Oct 30
United Airlines Logo
9:04 pm - 2:44 pmANC-SJU
13h 40m1 stop
United Airlines Logo
1:05 am - 7:59 pmSJU-ANC
22h 54m2 stops
$814United Airlines
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Sat, Oct 4 - Tue, Oct 7
United Airlines Logo
11:49 pm - 5:30 pmANC-SJU
13h 41m1 stop
United Airlines Logo
1:05 am - 7:57 pmSJU-ANC
22h 52m2 stops
$834United Airlines
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Thu, Oct 23 - Mon, Oct 27
American Airlines Logo
7:52 pm - 2:25 pmANC-SJU
14h 33m1 stop
American Airlines Logo
7:05 am - 6:44 pmSJU-ANC
15h 39m2 stops
$844American Airlines
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Sun, Dec 14 - Wed, Jan 14
 Logo
2:26 am - 3:35 pmANC-PUJ
32h 09m2 stops
 Logo
4:30 pm - 10:27 pmPUJ-ANC
34h 57m2 stops
Sat, Oct 4 - Wed, Oct 8
Alaska Airlines Logo
4:34 pm - 2:15 pmANC-SJU
17h 41m2 stops
Alaska Airlines Logo
3:34 pm - 4:31 pmSJU-ANC
28h 57m3 stops
$996Alaska Airlines
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Sat, Jan 24 - Sat, Jan 31
Alaska Airlines Logo
11:25 pm - 10:14 pmANC-SJU
17h 49m3 stops
Alaska Airlines Logo
7:20 am - 1:27 amSJU-ANC
23h 07m2 stops
$1,045Alaska Airlines
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Sun, Dec 14 - Wed, Jan 14
 Logo
12:38 am - 1:35 pmANC-PUJ
31h 57m2 stops
 Logo
2:30 pm - 12:12 amPUJ-ANC
38h 42m2 stops
$1,097
Find Deal
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 $626, 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 August, when tickets cost $717 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $1,282 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
Cheapest flight$322
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 17% 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.

  • 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
8.5Crew
8.1Boarding
7.8Comfort
7.1Food
7.0Entertainment
Airline reviews

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

6.0 GoodAnonymous, Aug 2025JNU - SEA
Read more Alaska Airlines reviews

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.

Paid extra $230 to check frozen fish on arrival to LAX. I was told my bags miss my flight and we’re gonna be on the next flight that comes in two hours later regrettably my family was here to pick me up so I had to drive all the way home to drop them off then turn around and come back if I had waited on Alaska to deliver them they told me that they would be delivered in 4 to 6 hours after 8 AM tomorrow which would’ve caused the fish to spoil stink and be a lost cause they would’ve put about $2500 worth of fish down the drain very unhappy with Alaska Airlines for not getting my baggage here, especially since I had to pay for the extra service

I was very pleased with this trip from Anchorage to Seattle and Seattle to Billings. Wheelchair assistance was rendered and gratefully accepted. Unlike my outbound flights to Seattle I did not have long, painful walks on a bad knee to get to airport gates. My thanks to the Alaska staff.

Jammed up security line. Security personnel excellent but facility is really cramped and lines long. Alaska Airlines was excellent.

Everything was great. Paid for upgraded economy seat and it was worth it: early boarding, roomy seat, great entertainment choices, free drink!

Horrible. Boarded late, sat on the tarmac for over an hour, missed my connecting flight and had to spend a day in the Seattle airport. I won’t be flying Hawaiian again.

When I booked with Kayak, I paid extra for a window seat for the long flight, so I could sleep more easily. But when I checked in, they changed my seat to a middle seat. This happened on both long flights to and from Chicago to Anchorage. For one flight, upon request they changed my seat back to a window seat. For the other, they would not and said the Alaska Airlines does not allow seat requests.....just disappointing.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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