$318 Find Cheap Flights from Anchorage to Caribbean

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 departing on 6/10. 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

Travelers love KAYAK
41’299’237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

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

Free to useThere are no hidden charges or fees.

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

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Anchorage to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$1,003
Santo Domingo
Santo Domingo1 stop$943
Nassau
Nassau2 stops$729
Saint Thomas Island
Saint Thomas Island2 stops$1,193
Kingston
Kingston2 stops$1,326
Punta Cana
Punta Cana2 stops$1,003
Santo Domingo
Santo Domingo1 stop$943
Nassau
Nassau2 stops$729
Saint Thomas Island
Saint Thomas Island2 stops$1,193
Kingston
Kingston2 stops$1,326

Book Cheap Anchorage to Caribbean 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 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

Wed, Sep 23 - Mon, Sep 28
United Airlines Logo
3:30 pm - 1:50 pm
ANC
-
NAS
18h 20m
2 stops
United Airlines Logo
2:53 pm - 7:45 pm
NAS
-
ANC
32h 52m
2 stops
$729United Airlines
Tue, Aug 11 - Sun, Sep 13
Southwest Logo
11:15 pm - 6:10 pm
ANC
-
SJU
14h 55m
2 stops
Southwest Logo
5:30 am - 11:45 pm
SJU
-
ANC
22h 15m
2 stops
$790Southwest
Mon, May 25 - Fri, Jun 5
Delta Logo
1:55 am - 8:30 pm
ANC
-
SJU
14h 35m
2 stops
Delta Logo
7:05 am - 12:55 am
SJU
-
ANC
21h 50m
2 stops
$815Delta
Fri, May 29 - Fri, Jun 5
United Airlines Logo
8:20 pm - 11:28 am
ANC
-
NAS
11h 08m
1 stop
United Airlines Logo
3:59 pm - 11:10 am
NAS
-
ANC
23h 11m
2 stops
$829United Airlines
Sun, May 24 - Wed, Jun 3
Delta Logo
8:05 pm - 12:01 pm
ANC
-
SJU
11h 56m
1 stop
Delta Logo
7:05 am - 12:55 am
SJU
-
ANC
21h 50m
2 stops
$848Delta
Sat, Jun 6 - Sat, Jun 27
Delta Logo
2:20 pm - 12:00 pm
ANC
-
SJU
17h 40m
2 stops
Delta Logo
4:21 pm - 1:23 am
SJU
-
ANC
13h 02m
1 stop
$855Delta
Fri, May 29 - Fri, Jun 5
American Airlines Logo
8:17 pm - 2:46 pm
ANC
-
NAS
14h 29m
1 stop
American Airlines Logo
12:42 pm - 8:41 pm
NAS
-
ANC
11h 59m
1 stop
$940American Airlines
Sun, May 31 - Sun, Jun 7
American Airlines Logo
9:53 pm - 5:50 pm
ANC
-
NAS
15h 57m
2 stops
American Airlines Logo
8:00 am - 10:35 pm
NAS
-
ANC
18h 35m
2 stops
$954American Airlines
Sat, Sep 5 - Wed, Sep 9
Air Canada Logo
2:40 pm - 1:15 pm
ANC
-
AZS
18h 35m
2 stops
Air Canada Logo
8:05 pm - 1:35 pm
AZS
-
ANC
45h 30m
2 stops
$1,836Air Canada
Fri, May 29 - Fri, Jun 5
Multiple Airlines Logo
2:40 pm - 5:30 pm
ANC
-
NAS
22h 50m
2 stops
Multiple Airlines Logo
12:00 pm - 1:36 pm
NAS
-
ANC
29h 36m
3 stops
$1,874Multiple Airlines
Booking Insights

KAYAK's insights & trends for Anchorage to Caribbean flights

Get data-powered insights and trends into flights from Anchorage to Caribbean to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Anchorage to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Anchorage to Caribbean were found on United Airlines ($729) and American Airlines ($729).

Good to know

Low seasonApril
Cheapest flight$318
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Anchorage to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Anchorage to Caribbean?

    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.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Anchorage to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Anchorage to Caribbean 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?

    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 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?

    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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Anchorage to Caribbean

 
Need help choosing which airline to fly with from Anchorage to Caribbean? 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.
7.9
DeltaOverall score based on 8424 reviews
8.5Crew
7.8Entertainment
7.9Comfort
7.2Food
8.1Boarding
Airline reviews

The flight was way too HOT! And the plane did not have any in-flight TV entertainment.

6.0 GoodEvelyn, Apr 2026
MDT - ATL
Read more Delta reviews

The flight was way too HOT! And the plane did not have any in-flight TV entertainment.

Boarding was good. The flight was on time ( arrival was 20 minutes early). Inflight service was average ( US airlines have not mastered the skills of customer service yet). The food was mediocre. “ breakfast “ was downright awful and insulting. It was a piece of dough with mon descript filling that was supposed to be cheese omelette).

The tray table was broken and the food was terrible.

The gentleman at the gate I think his name is RIE was exceptional

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

No entertainment. Plane was so small had to pink tag a carry on ive used for 20 years easily on board. The fact the flight got in at midnight, had to wait for crew in fort wayne to allow the plane to approach the gate, THEN had to wait for bag on jet bridge made experience irritating at best.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

Would have been better if there was a nonstop flight from Tampa to Norfolk or Tampa to New Port News.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The entertainment options on the seat back video boards were nice.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

Due to cancellation of connecting flight (Lufthansa) I didn’t fly with United

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

It was a red-eye, but the flight felt surprisingly quick. The seats were very comfortable, and that made resting much easier. I also want to thank the gentleman seated next to me, who graciously moved so my mom could sit beside me. We slept almost the entire way. The cabin crew was respectful in not disturbing us, while also being courteous and professional throughout. Thank you, United.

Packed in plane small uncomfortable seats elbow to elbow nobody wants to be in that situation for the money they paid

Vegetarian selection could be better. Bread was too hard to chew.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports