$237 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 9/2. 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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Flights Deals

Best Caribbean Islands Flight Deals from Anchorage

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$928
Santo Domingo
Santo Domingo1 stop$868
Nassau
Nassau2 stops$588
Saint Thomas Island
Saint Thomas Island2 stops$1,242
Kingston
Kingston2 stops$1,094
Puerto Plata
Puerto Plata2 stops$1,068
Punta Cana
Punta Cana2 stops$928
Santo Domingo
Santo Domingo1 stop$868
Nassau
Nassau2 stops$588
Saint Thomas Island
Saint Thomas Island2 stops$1,242
Kingston
Kingston2 stops$1,094
Puerto Plata
Puerto Plata2 stops$1,068

Cheap Flights from Anchorage to Caribbean Islands

 
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, Oct 21 - Thu, Oct 30
Delta Logo
12:40 am - 1:11 pmANC-NAS
32h 31m2 stops
Delta Logo
1:23 pm - 1:00 amNAS-ANC
15h 37m2 stops
$588Delta
Find Deal
Thu, Oct 23 - Tue, Oct 28
American Airlines Logo
7:52 pm - 5:47 pmANC-NAS
17h 55m2 stops
American Airlines Logo
7:45 am - 6:44 pmNAS-ANC
14h 59m2 stops
$592American Airlines
Find Deal
Wed, Oct 22 - Mon, Oct 27
Delta Logo
10:40 am - 1:11 pmANC-NAS
22h 31m2 stops
Delta Logo
2:36 pm - 1:45 amNAS-ANC
15h 09m2 stops
$593Delta
Find Deal
Thu, Oct 23 - Sun, Oct 26
Delta Logo
5:15 pm - 11:58 amANC-NAS
14h 43m2 stops
Delta Logo
1:23 pm - 1:00 amNAS-ANC
15h 37m2 stops
$598Delta
Find Deal
Sun, Sep 14 - Sun, Sep 21
Delta Logo
2:15 pm - 11:30 amANC-NAS
17h 15m2 stops
Delta Logo
12:55 pm - 1:37 amNAS-ANC
16h 42m2 stops
$619Delta
Find Deal
Sun, Sep 14 - Sun, Sep 21
Delta Logo
2:15 pm - 11:30 amANC-NAS
17h 15m2 stops
Delta Logo
12:55 pm - 1:37 amNAS-ANC
16h 42m2 stops
$642Delta
Find Deal
Sat, Sep 27 - Tue, Sep 30
American Airlines Logo
9:53 pm - 11:37 pmANC-SJU
21h 44m2 stops
American Airlines Logo
3:55 pm - 8:48 pmSJU-ANC
32h 53m2 stops
$648American Airlines
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Fri, Nov 7 - Sat, Nov 15
United Airlines Logo
9:07 pm - 3:03 pmANC-NAS
13h 56m1 stop
United Airlines Logo
2:55 pm - 10:56 pmNAS-ANC
12h 01m1 stop
$693United Airlines
Find Deal
Fri, Nov 7 - Sat, Nov 15
United Airlines Logo
9:07 pm - 3:03 pmANC-NAS
13h 56m1 stop
United Airlines Logo
1:05 pm - 10:56 pmNAS-ANC
37h 51m2 stops
$726United Airlines
Find Deal
Sun, Sep 7 - Sat, Sep 13
Air Canada Logo
4:45 pm - 3:20 pmANC-PUJ
18h 35m2 stops
Air Canada Logo
4:25 pm - 3:56 pmPUJ-ANC
27h 31m2 stops
$954Air Canada
Find Deal
Useful Info

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 $948, 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 $782 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $1,292 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
High seasonDecember
Cheapest flight$237
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from Anchorage to Nassau

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

Flight from New Orleans to Seattle to Anchorage was delayed for 3 hours My flight from Seattle to Anchorage was not rescheduled. I had to call the airlines to tell them to get a flight from Seattle to Anchorage they finally got me a flight If I hadn’t been aware of this problem I don’t know how long I would of waited in Seattle to get a flight to Anchorage!!!!!! Return trip from Anchorage to New Orleans in Seattle to New Orleans I was at the right gate when I realized something was wrong they had changed the gate without notifying the change l finally made it on time with minutes to spare & exhausted

10.0 ExcellentAnonymous, Jun 2025ANC - SEA
Read more Alaska Airlines reviews

Flight from New Orleans to Seattle to Anchorage was delayed for 3 hours My flight from Seattle to Anchorage was not rescheduled. I had to call the airlines to tell them to get a flight from Seattle to Anchorage they finally got me a flight If I hadn’t been aware of this problem I don’t know how long I would of waited in Seattle to get a flight to Anchorage!!!!!! Return trip from Anchorage to New Orleans in Seattle to New Orleans I was at the right gate when I realized something was wrong they had changed the gate without notifying the change l finally made it on time with minutes to spare & exhausted

Could have service kiosks, had to find a gate with an attendant

The flight was short and smooth. The crew was friendly and courteous.

It sucks, flight delays at FAT caused us to miss a day at lodge and overnight in Seattle. Flight delays coming home also. Never again

Like the friendliness of the crew, each flight had a very very drunk person next to me and the last flight had a very obese man pushing me into the aisle while the crew kept ending up hitting me in the shoulder with the beverage carts.

Booked a first class ticket from Anchorage to Seattle but was denied complimentary access to Alaska Lounge as our 1500 mile flight wasn’t long enough’

It was very good. I love flying with Alaska air.

Flying sucks these days. No airline is better than another. Alaska Air At least gives you some pretzel snacks. That is about all I can say for it.

Boarding for Alaska Airlines is always chaotic with many people crowding the gates. Arriving in on Alaska in Los Angeles is always interesting since there is never a gate available. So the planes are often parked all the way out on the west side of the airport while waiting for the gate to be cleared of the departing plane. This flight was no exception.

The would have rated higher, but I asked for a cup of coffee twice and never got one. Later found the crew sitting in the back having a meal and visiting. Just saying.

Great. Very smooth. Plenty of information. However, wish they would give out a menu in advance of making a dinner choice like other international airlines. The flight attendant says chicken or pasta and there are details about ingredients or spices requiring the passenger to ask which requires the flight attendant to answer many times. So easy to solve this problem. P

I'm a tall guy and even the seats with more leg room were not as comfortable as I had hoped.

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

They delayed our flight because of bad weather in NY which was completely understandable. Then they cancelled our flight and a later flight that evening. The earliest we could fly was the next morning. We ended up buying last minute tickets on another airline and made it home slightly delayed but safely that evening. Delta kept saying it was weather related but if that was the case how did we make it back on another airline? The weather in NY was cloudy but not bad.

From Atlanta to Savannah - flight connection was way to short (we weren't even late landing ) and flight was already boarding when we landed - we were told we were the last on board and so we had to gate check our bags. Once we got on the plane, there were at least seven open bag spots so that was unnecessary delay. There should be better communication between the gate agent and the crew.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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