$353 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 12/3. 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

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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$926
Santo Domingo
Santo Domingo2 stops$881
Nassau
Nassau2 stops$586
Saint Thomas Island
Saint Thomas Island2 stops$1,045
Kingston
Kingston2 stops$1,255
Puerto Plata
Puerto Plata2 stops$926
Punta Cana
Punta Cana2 stops$926
Santo Domingo
Santo Domingo2 stops$881
Nassau
Nassau2 stops$586
Saint Thomas Island
Saint Thomas Island2 stops$1,045
Kingston
Kingston2 stops$1,255
Puerto Plata
Puerto Plata2 stops$926

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

Fri, Nov 7 - Sat, Nov 15
Delta Logo
6:05 am - 11:51 amANC-NAS
25h 46m2 stops
Delta Logo
4:51 pm - 1:23 pmNAS-ANC
24h 32m2 stops
$586Delta
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Wed, Dec 3 - Wed, Dec 10
Delta Logo
5:37 pm - 3:43 pmANC-NAS
18h 06m2 stops
Delta Logo
2:55 pm - 1:53 amNAS-ANC
14h 58m2 stops
$588Delta
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Fri, Nov 7 - Sat, Nov 15
United Airlines Logo
11:59 pm - 4:14 pmANC-NAS
12h 15m1 stop
United Airlines Logo
2:55 pm - 10:56 pmNAS-ANC
12h 01m1 stop
$696United 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
$698United Airlines
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Sun, Dec 21 - Thu, Jan 8
American Airlines Logo
8:30 pm - 11:22 pmANC-SJU
21h 52m1 stop
American Airlines Logo
6:00 am - 9:51 pmSJU-ANC
20h 51m2 stops
$924American Airlines
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Sun, Dec 7 - Fri, Dec 26
American Airlines Logo
5:24 pm - 2:44 pmANC-SJU
16h 20m2 stops
American Airlines Logo
1:30 am - 6:58 pmSJU-ANC
22h 28m1 stop
$949American Airlines
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Wed, Jan 14 - Sat, Feb 7
Alaska Airlines Logo
3:54 pm - 10:22 pmANC-SJU
25h 28m2 stops
Alaska Airlines Logo
7:00 am - 10:52 pmSJU-ANC
20h 52m3 stops
$1,040Alaska Airlines
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Wed, Jan 7 - Thu, Feb 19
Alaska Airlines Logo
12:49 am - 9:39 pmANC-SJU
15h 50m2 stops
Alaska Airlines Logo
8:04 am - 1:27 amSJU-ANC
22h 23m3 stops
$1,059Alaska Airlines
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Thu, Dec 25 - Sat, Feb 7
Multiple Airlines Logo
8:30 pm - 9:04 pmANC-STI
19h 34m2 stops
Multiple Airlines Logo
4:37 pm - 2:17 pmSTI-ANC
26h 40m2 stops
$1,134Multiple Airlines
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Wed, Dec 24 - Sat, Jan 31
Multiple Airlines Logo
8:30 pm - 9:04 pmANC-STI
19h 34m2 stops
Multiple Airlines Logo
6:02 am - 12:59 amSTI-ANC
23h 57m2 stops
$1,156Multiple Airlines
Find Deal
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.

What is the cheapest month to fly from Anchorage to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Anchorage to Caribbean, 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 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?

The average price of all round-trip flights from Anchorage to Caribbean clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Caribbean on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Thursday is the most expensive day to fly from Anchorage to Caribbean. For your return ticket, we recommend flying on a Monday and avoiding Fridays for the best deals.

Good to know

Low seasonAugust
Cheapest flight$353
Best time to beat the crowds with an average 57% drop in price.
Most popular time to fly and prices are also 20% lower on average.
Flight from Anchorage to Santiago de los Caballeros

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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean 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 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 4 airlines serving 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.
8.0
Alaska AirlinesOverall score based on 11094 reviews
8.1Boarding
7.0Entertainment
7.1Food
8.5Crew
7.8Comfort
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!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

On time flight. Seat comfort could be better in the Comfort section.

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

The flight was an hour and a half late departing which was inconvenient

Delay in SLC jammed us up in Chicago. Got caught up in rush hour traffic

The crew took good care of us. The flight from ATL to SFO is a longer one, and there were multiple beverage offerings. I like the 757's that Delta uses. Good airplane that is comfortable. I do wish Delta would separate Priority boarding from the better seats. I would gladly take a smaller seat in an open row than be jammed into Comfort just to get priority boarding, just to make sure I don't have to check a bag.

The flight was great. The gate location was way to far away!!!

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

The entertainment available didn’t work for anyone on the flight. Long 6 hr flight with no entertainment option and the staff didn’t know until an hour into the flight when we made sure they knew about it. They had no way to fix it.

Crew seemed a bit cranky. No seatback screens. But boarding was efficient and on time and we arrived early.

The worst landing I have ever had on a domestic flight. Thought we would lose the landing gear on landing in Newark. Then we spent 40 minutes trying to position the plane in the right place to be able to get the jet way to the plane. The plane arrived stopped. The announcer was that we were there. Everybody got up, then we were told to sit back down because they had to have us towed to a different position. We got towed and then everyone stood up and they told us we were in the wrong position to sit back down again, and then we got towed to a different position This did not happen immediately. It was 30 minutes while we wandered around a small section of the tarmac in Newark close to the gate, but apparently not close enough. Horrifying experience The CAB should be investigating that flight

Food was poorly timed and not good.. Hand held snacks, really. I kept asking for water and never got any. Service was rushed for a 7-hour flight.

Boarding was organized. Old plane. Seat fairly comfortable. Business Class much too large so you don’t receive as much attention as you should considering what you pay for the seat.

Boarding was organized. Plane seats comfortable and service was attentive. Food options were good.

This was a very average flight. The seat was out of alignment so more uncomfortable than usual. The cabin felt not well maintained. But I safely got where I needed to go.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

Flight attendants on this flight were very attentive and friendly

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Food should be better quality. Video screens have poor resolution and the library of movies is poor. The other airlines are much better.

the trip to madrid was uncomfortable with my legs touching the seat in front of me

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My flight was delayed for 17hs because the pilot forgot his passport!!! What a joke. AA used to be a great airline, now I have to think twice before flying with them again.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Everything you need to know for your flight to Caribbean

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