$312 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 3/23. 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 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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Flight Deals

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$957
Santo Domingo
Santo Domingo2 stops$902
Nassau
Nassau1 stop$644
Santiago de los Caballeros
Santiago de los Caballeros2 stops$902
Saint Thomas Island
Saint Thomas Island2 stops$895
Kingston
Kingston2 stops$1,151
Punta Cana
Punta Cana2 stops$957
Santo Domingo
Santo Domingo2 stops$902
Nassau
Nassau1 stop$644
Santiago de los Caballeros
Santiago de los Caballeros2 stops$902
Saint Thomas Island
Saint Thomas Island2 stops$895
Kingston
Kingston2 stops$1,151

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

Sat, Apr 25 - Sat, May 2
United Airlines Logo
8:50 pm - 2:57 pm
ANC
-
NAS
14h 07m
1 stop
United Airlines Logo
3:10 pm - 10:45 pm
NAS
-
ANC
11h 35m
1 stop
$644United Airlines
Tue, Apr 7 - Tue, Apr 14
United Airlines Logo
8:50 pm - 2:57 pm
ANC
-
NAS
14h 07m
1 stop
United Airlines Logo
3:59 pm - 7:48 pm
NAS
-
ANC
31h 49m
1 stop
$655United Airlines
Thu, Apr 9 - Thu, Apr 16
United Airlines Logo
11:47 pm - 11:55 am
ANC
-
NAS
32h 08m
2 stops
United Airlines Logo
2:53 pm - 7:48 pm
NAS
-
ANC
32h 55m
2 stops
$663United Airlines
Sat, Apr 25 - Sat, May 2
American Airlines Logo
8:30 pm - 2:44 pm
ANC
-
NAS
14h 14m
1 stop
American Airlines Logo
3:44 pm - 6:50 pm
NAS
-
ANC
31h 06m
1 stop
$664American Airlines
Sat, Apr 25 - Sat, May 2
American Airlines Logo
8:30 pm - 8:27 pm
ANC
-
NAS
19h 57m
2 stops
American Airlines Logo
3:44 pm - 6:50 pm
NAS
-
ANC
31h 06m
1 stop
$668American Airlines
Sat, May 2 - Thu, May 7
Delta Logo
9:15 pm - 4:23 pm
ANC
-
SJU
15h 08m
2 stops
Delta Logo
2:25 pm - 12:31 am
SJU
-
ANC
14h 06m
2 stops
$795Delta
Thu, May 28 - Sun, Jun 7
Delta Logo
5:20 pm - 4:33 pm
ANC
-
SJU
19h 13m
2 stops
Delta Logo
2:35 pm - 1:35 am
SJU
-
ANC
15h 00m
2 stops
$815Delta
Mon, May 25 - Mon, Jun 8
Southwest Logo
11:55 pm - 10:40 pm
ANC
-
SJU
18h 45m
2 stops
Southwest Logo
6:00 am - 10:10 pm
SJU
-
ANC
20h 10m
2 stops
$830Southwest
Sun, May 17 - Sun, May 24
Multiple Airlines Logo
2:40 pm - 1:55 pm
ANC
-
KIN
44h 15m
2 stops
Multiple Airlines Logo
8:05 am - 1:36 pm
KIN
-
ANC
32h 31m
2 stops
$1,151Multiple Airlines
Sun, May 17 - Sun, May 24
Multiple Airlines Logo
2:40 pm - 1:55 pm
ANC
-
KIN
44h 15m
2 stops
Multiple Airlines Logo
8:05 am - 1:36 pm
KIN
-
ANC
32h 31m
3 stops
$1,159Multiple 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 $635, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonAugust
Cheapest flight$312
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly with an average 6% 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.

Reviews of the top airline 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.
7.9
DeltaOverall score based on 8239 reviews
7.9Comfort
7.8Entertainment
7.2Food
8.5Crew
8.1Boarding
Airline reviews

2+hrs delay without any reason provided and a cramped flight

2.0 MediocreYogendra Kumar, Feb 2026
DTW - MDT
Read more Delta reviews

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

Never got on it. Was re-routed through Detroit and am still in airports 12 hours later waiting for my connecting plane to arrive.

Delta has too many delays now days. It is 1:06 am now. I was supposed to land in Norfolk at 10:30 pm. I got re-booked through Detroit and I’m still in Detroit. I hope to be landed in Norfolk by 3am. I’ve been in airports for 12 hours as of right now. There is a weather delay now but most delays lately have been maintenance.

Very Very late. Subsequent flights left an hour before ours

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Anchorage (ANC)