$398 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 8/31. 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.
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1 adult, Economy, 0 bags

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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 Cana1 stop$998
Santo Domingo
Santo Domingo2 stops$993
Nassau
Nassau1 stop$798
Saint Thomas Island
Saint Thomas Island2 stops$1,290
Kingston
Kingston2 stops$1,407
Punta Cana
Punta Cana1 stop$998
Santo Domingo
Santo Domingo2 stops$993
Nassau
Nassau1 stop$798
Saint Thomas Island
Saint Thomas Island2 stops$1,290
Kingston
Kingston2 stops$1,407

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, Sep 6 - Sun, Sep 13
United Airlines Logo
8:19 pm - 11:28 amANC  Anchorage-NAS Nassau Intl
11h 09m1 stop Newark
United Airlines Logo
2:35 pm - 7:59 pmNAS  Nassau Intl-ANC Anchorage
33h 24m2 stops Newark Chicago O'Hare Intl
$798United Airlines
Thu, Sep 3 - Sun, Sep 6
United Airlines Logo
9:20 pm - 2:44 pmANC  Anchorage-SJU San Juan Luis Munoz Marin Intl
13h 24m1 stop Chicago O'Hare Intl
United Airlines Logo
1:00 am - 1:04 pmSJU  San Juan Luis Munoz Marin Intl-ANC Anchorage
16h 04m2 stops Newark Chicago O'Hare Intl
$815United Airlines
Thu, Jan 7 - Tue, Jan 19
United Airlines Logo
8:44 pm - 3:40 pmANC  Anchorage-SJU San Juan Luis Munoz Marin Intl
13h 56m1 stop Chicago O'Hare Intl
United Airlines Logo
2:25 pm - 10:39 pmSJU  San Juan Luis Munoz Marin Intl-ANC Anchorage
13h 14m1 stop Denver Intl
$815United Airlines
Sun, Oct 18 - Mon, Nov 2
Delta Logo
10:09 pm - 4:49 pmANC  Anchorage-SJU San Juan Luis Munoz Marin Intl
14h 40m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson
Delta Logo
7:45 am - 12:35 amSJU  San Juan Luis Munoz Marin Intl-ANC Anchorage
21h 50m2 stops New York John F Kennedy Intl Seattle/Tacoma Intl
$835Delta
Sun, Oct 18 - Mon, Nov 2
Delta Logo
4:05 pm - 11:40 amANC  Anchorage-SJU San Juan Luis Munoz Marin Intl
15h 35m2 stops Seattle/Tacoma Intl Atlanta Hartsfield-Jackson
Delta Logo
7:45 am - 12:35 amSJU  San Juan Luis Munoz Marin Intl-ANC Anchorage
21h 50m2 stops New York John F Kennedy Intl Seattle/Tacoma Intl
$835Delta
Sun, Oct 18 - Mon, Nov 2
Delta Logo
2:29 pm - 1:49 pmANC  Anchorage-SJU San Juan Luis Munoz Marin Intl
19h 20m2 stops Seattle/Tacoma Intl Atlanta Hartsfield-Jackson
Delta Logo
7:45 am - 12:35 amSJU  San Juan Luis Munoz Marin Intl-ANC Anchorage
21h 50m2 stops New York John F Kennedy Intl Seattle/Tacoma Intl
$835Delta
Sat, Sep 5 - Sun, Sep 13
Multiple Airlines Logo
1:29 am - 8:45 pmANC  Anchorage-NAS Nassau Intl
15h 16m2 stops Seattle/Tacoma Intl Miami
Multiple Airlines Logo
11:30 am - 11:15 amNAS  Nassau Intl-ANC Anchorage
27h 45m2 stops Fort Lauderdale Seattle/Tacoma Intl
$933Multiple Airlines
Thu, Oct 1 - Sat, Oct 10
American Airlines Logo
9:54 pm - 8:47 pmANC  Anchorage-SJU San Juan Luis Munoz Marin Intl
18h 53m2 stops Chicago O'Hare Intl Miami
American Airlines Logo
6:00 am - 5:29 pmSJU  San Juan Luis Munoz Marin Intl-ANC Anchorage
15h 29m2 stops Dallas/Fort Worth Seattle/Tacoma Intl
$960American Airlines
Thu, Sep 3 - Mon, Sep 7
American Airlines Logo
9:56 pm - 9:55 pmANC  Anchorage-SJU San Juan Luis Munoz Marin Intl
19h 59m2 stops Chicago O'Hare Intl Miami
American Airlines Logo
6:00 am - 8:51 pmSJU  San Juan Luis Munoz Marin Intl-ANC Anchorage
18h 51m2 stops Miami Chicago O'Hare Intl
$965American Airlines
Wed, Sep 2 - Wed, Sep 9
Multiple Airlines Logo
10:28 pm - 12:30 pmANC  Anchorage-PUJ Punta Cana
34h 02m1 stop Chicago O'Hare Intl
Multiple Airlines Logo
1:01 pm - 10:04 amPUJ  Punta Cana-ANC Anchorage
25h 03m2 stops Miami Seattle/Tacoma Intl
$998Multiple Airlines
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 $709, 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 July and May, when the average cost of round-trip tickets is $1,375 and $1,261 respectively.

Good to know

Low season

April

Cheapest flight

$398
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 8% lower on average.
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.

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 8504 reviews
7.8Comfort
7.8Entertainment
8.1Boarding
7.2Food
8.5Crew
Airline reviews

There is consistently no communication/updated time slots in the app on when a flight will board when its delayed, which is the most frustrating as a consumer trying to understand if they need to get food now, or if there is actually a chance for them to eat during their layover. This keeps being my experience with delta and a potential reason to change airlines.

4.0 OkayStacey, Aug 2026
Read more Delta reviews

There is consistently no communication/updated time slots in the app on when a flight will board when its delayed, which is the most frustrating as a consumer trying to understand if they need to get food now, or if there is actually a chance for them to eat during their layover. This keeps being my experience with delta and a potential reason to change airlines.

Long delays at both DCA and MSP; Crew did not keep us informed (or very little). Airplane was showing signs of heavy use (not up to Delta standards). Food options for Business Class have dropped in quality. After landing we sat on tarmac for maybe 25 minutes with no provided chance to use the bathroom and crew did not tell us what was going on or give an estimated time to expect to be at a gate.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Lounge in Lagos is terrible, food on board from Lagos to Atlanta was horrible. Only bright spot the cabin crew were awesome.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

Food from the flight from Atlanta to Santiago was very poor..

Delta was great the entertainment was outdated. Screen was very small and didn’t work.

The boarding was great. With all the delays I was grateful to get on the plane and headed for home. There was no in flight entertainment. Seats were very uncomfortable! Unfortunately we were seated next to an exit row so there was no recline in our seat. Other than that it was a smooth ride.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

Delta is one of the best airlines I have flown

Like the fact that the boarding was expedited. But the delay and chaos around the onboarding was not appreciated.

Flight was 2.5 late. Maybe not United’s fault but late none the less. We were late as well on the first leg. WiFi quit working with an hour left.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

The flight to America was freezing. The overnight flight back to the UK was boiling hot and the cabin stank of toilet or occasionally perfume, even though I was several rows back from either bathroom. Food was tiny portions. Two small pieces of tough and dry beef in random gravy with pretend mashed potato raking up most of it. Very little veg. Salad was ok. Wooden cutlery broke within minutes of using. Lots of old films for entertainment. Some new ones. Generally a bit rubbish.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

Staff and flight attendants were very polite. Flight was smooth. My seat on the plane was a bit broken so it would not stay in upright position but it was fine for the most part.

There was no food available for this red eye... one little waffle cookie for a 6+ hour flight... thank God I was able to sleep some

To san Francisco it was ok. From sf to Manila it was horrible

You have got to come up with a better way of getting connecting flight people off the plane first. Flying doesn’t bring out the best in people but exiting off a plane rules needs to come from management, not from the expectation that passengers will be “kind” and let them off first. Perhaps exiting in zones? Like boarding? Zone 1 exits are connecting people. This frustration led to many people missing their flights or scrambling. We were delayed leaving the first leg which amplified this.

Pilot main message was to "be nice to her crew". Crew only instructed passenger to "move out of the aisles" rather than helping passengers place their luggage. Some passengers needed to exit early to make their connections yet cleaning crews rushed onboard to make their way past rushing outgoing passengers. AA needs better protocols and better customer service for the price paid for trips.

Inflight wifi was awful. Couldn't connect for the first hour until they manually reset, and after that the connection kept dropping every five minutes. Their entertainment option streamed fine but normal browsing was unusable.

Did not know that they didn’t have screens for entertainment. I didn’t have headphones so I couldn’t watch anything on my phone.

Delayed couple hours due to airplane maintenance issues, we boarded and then asked to unboard, but cmon!! Can they do the whole maintenance prior to boarding?

No food. I paid over $1.000 for my ticket for nuts and espresso beans.

I was so hungry. No meals. Staff very nice. Seat arms armed too tight and didn’t go up. I was scheduled for First class, but was put on Standby, even though I made my reservation a while ago. Thank you.

Boarding was horrendous! Took absolutely forever… and the delay from the broken coffee pot was really kind of ridiculous

I take this flight about 6-8 times per year. It is convenient and saves an hour or two by skipping PDX, SEA, PHX, or ORD (but it takes longer to get bags to the carousel than Alaska Airlines). I wish the food service were better (but they might cut back on it because it is a red-eye). The WifI seems to go down about an hour out of Anchorage, and then comes back about an hour later...so be warned if this is an issue for you.

Flight was good. However, they had everyone board the plane then made us sit there on the tarmac for an hour plus due to maintenance issues. Besides that flight attendant and pilot were amazing.

Check in agent was helpful and nice. Flight was OK. Our flight in Chicago was delayed 8 hours without an explination. This was our journey home. After a horrible flight experience on on the way to our vacation where our plane was diverted for an emergency medical issue, was grounded for hours, we missed our connecting flight by 25 minutes, and it took a day yo get re-booked, this was yet another bad experience that American seemed unwilling to help out with, much less compensate us for the

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports