$373 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 10/6. 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$930
Santo Domingo
Santo Domingo2 stops$878
Nassau
Nassau2 stops$683
Kingston
Kingston2 stops$1,094
Puerto Plata
Puerto Plata2 stops$1,038
Punta Cana
Punta Cana2 stops$930
Santo Domingo
Santo Domingo2 stops$878
Nassau
Nassau2 stops$683
Kingston
Kingston2 stops$1,094
Puerto Plata
Puerto Plata2 stops$1,038

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

Sun, Nov 2 - Wed, Nov 12
United Airlines Logo
9:07 pm - 10:22 pmANC-SJU
20h 15m2 stops
United Airlines Logo
2:05 am - 7:59 pmSJU-ANC
22h 54m2 stops
$654United Airlines
Find Deal
Sat, Oct 4 - Tue, Oct 7
United Airlines Logo
11:49 pm - 2:44 pmANC-SJU
34h 55m2 stops
United Airlines Logo
1:05 am - 7:57 pmSJU-ANC
22h 52m2 stops
$680United Airlines
Find Deal
Wed, Oct 22 - Fri, Oct 31
Delta Logo
12:30 am - 11:56 pmANC-SJU
19h 26m2 stops
Delta Logo
7:15 am - 10:43 pmSJU-ANC
19h 28m2 stops
$764Delta
Find Deal
Wed, Oct 22 - Mon, Oct 27
Delta Logo
12:30 am - 11:56 pmANC-SJU
19h 26m2 stops
Delta Logo
2:22 pm - 1:59 amSJU-ANC
15h 37m2 stops
$784Delta
Find Deal
Sun, Oct 5 - Sun, Oct 12
American Airlines Logo
8:13 pm - 3:54 pmANC-SJU
15h 41m2 stops
American Airlines Logo
7:00 am - 6:44 pmSJU-ANC
15h 44m2 stops
$909American Airlines
Find Deal
Mon, Oct 6 - Sun, Oct 12
American Airlines Logo
7:52 pm - 2:25 pmANC-SJU
14h 33m1 stop
American Airlines Logo
7:00 am - 6:44 pmSJU-ANC
15h 44m2 stops
$929American Airlines
Find Deal
Mon, Jan 19 - Fri, Jan 23
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
$1,023Alaska Airlines
Find Deal
Mon, Nov 3 - Tue, Nov 11
Alaska Airlines Logo
11:05 am - 3:06 pmANC-SJU
23h 01m2 stops
Alaska Airlines Logo
7:15 am - 2:04 amSJU-ANC
23h 49m3 stops
$1,057Alaska Airlines
Find Deal
Wed, Dec 10 - Thu, Jan 8
 Logo
11:20 am - 11:41 amANC-PUJ
19h 21m2 stops
 Logo
1:50 pm - 9:54 amPUJ-ANC
25h 04m2 stops
$1,215
Find Deal
Fri, Dec 19 - Wed, Jan 7
 Logo
8:30 pm - 5:49 pmANC-PUJ
16h 19m2 stops
 Logo
1:57 pm - 2:39 amPUJ-ANC
17h 42m2 stops
$1,374
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 $644, 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 $441 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $1,272 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$373
Best time to beat the crowds with an average 58% drop in price.
Most popular time to fly and prices are also 21% lower on average.
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
8.5Crew
8.1Boarding
7.8Comfort
7.0Entertainment
7.1Food
Airline reviews

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.

4.0 OkayAnonymous, Sep 2025SIT - SEA
Read more Alaska Airlines reviews

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.

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!

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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