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Find cheap flights from Anchorage to Caribbean Islands from $368

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 8/6. 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
0 bags
Sat 6/8
Sat 6/15

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Best Caribbean Islands Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana3 stops$916
Santo Domingo
Santo Domingo2 stops$853
Nassau
Nassau2 stops$562
Kingston
Kingston3 stops$953

Good to know

Low season

April

High season

December

Cheapest flight

$368
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 24% increase in price.
Flight from Anchorage to San Juan

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 to Caribbean Islands from Anchorage 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 to Caribbean Islands with an airline and back to Anchorage 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 to Caribbean Islands from Anchorage up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 airlines serving from Anchorage to Caribbean Islands

 
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 9140 reviews
7.9Comfort
7.3Entertainment
8.6Crew
8.2Boarding
7.3Food
Airline reviews

It was a very short flight. No snack or drink. The steward stayed seated the whole time. The plane was comfortable. Boarding in Pullman was a breeze, only 1 gate. I would definitely fly thru there again.

8.0 ExcellentAnonymous, May 2024PUW - BOI
Read more about Alaska Airlines reviews

It was a very short flight. No snack or drink. The steward stayed seated the whole time. The plane was comfortable. Boarding in Pullman was a breeze, only 1 gate. I would definitely fly thru there again.

After upgrading and paying for seat I was bumped from my seat. When I went to ask why she said I wasn’t assigned a seat because the ticket I purchased. After kindly explaining to her I upgraded the night before and paid for that seat she said how I was wrong and that something must have happened. I showed her my receipt and she still said there was an error. This is why I only fly delta. The flight attendant was rude as well but I don’t want to waste anymore time talking about how poor Alaska is. Delta here I come!

Flight cancelled an hour before takeoff due to "unscheduled maintenance". New flight makes me have to wait for 5 hours in the airport, at a gate totally on the other side of where I'm at, requiring me to take a tram to get from the N terminal, to the C terminal. After waiting for 5 hours I'm informed my new flight is no longer at the gate I'm at, but instead is back in the N terminal where I was previously.

Ashley - the flight attendant from OMA to SEA - was phenomenal. I was traveling alone with my 4 month old and she made every accommodation possible and went out of her way to make sure my experience was as comfortable as possible. Give this woman a massive raise!

No tv, movies for a 6 hour flight! Worst airline I have ever travelled!

boarding was easy and the 737 Max was comfortable and roomy but that was the only good.. there was a child screaming at the top of his lungs for the entire loading, taxiing and part of the flight and no one in the crew said anything or offered any assistance.

Delayed an hour and sat without updates. Ended up an hour late to destination

It was great; it was on time, everything went smoothly, the crew was excellent. It was just uncomfortable for the usual reasons; completely full fight, could barely move because the space was so small. The expected stuff with every airline.

The flight was decent again if there was a place that you could put crying children that would be great. Or maybe make a rule against allowing infants on the plane.

The flight was great. The pilot was great. It was really annoying that the staff had facemasks on. Hard to hear what they’re saying when a mask is covering their mouth. I enjoyed the flight, but there was a crying baby in front of me. You guys should offer flights baby free. I would be very into that me and the person next to me discussed how they should make free flights for all of us that don’t have kids. I wouldn’t mind paying extra to not have to deal with the smell of a dirty diaper or screaming of a child. Also, if they had a separate room, the babies could be sent to the back with a curtain or something muddle the horrible sounds.

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

Flight was delayed 2.5 hours - a big deal on an overnight when you plan to sleep.

I feel like they have upgraded the app since I last flew United and I found it to be super helpful. I had stopped flying United unless absolutely necessary and my experience on this trip indicates they have been working hard to improve their services.

Surprisingly easy! I was hesitant to try this, but the cost swayed me. I actually felt like I had less stress than all the taxiing and possible delays that occur with short regional flights where you spend less time in the air than getting to and from the plane..

This flight was delayed multiple times and eventually canceled around 2-3ish. Original take off time was around 10:30am. By 3, there were no other options out of Houston, so stuck in Houston for from 3pm - 11am the next day.

Should have video screens Plane audio was poor and without wired connection hard to understand crew. Should serve more than just cups of water and pretzels on six hour flight. Did not see crew rest of flight. Fix charging sockets to retain charging blocks.

I paid $380 for my one-way ticket from California to Minnesota. The fair did not include online check-in. I received instructions from their app to check in at a kiosk. At the kiosk, the boarding pass would not print until an actual person came to verify that I had a personal item and not a carry-on item, On the plane, the person next to me was drunk and allowed to continue to order alcohol. United is garbage I’d rather fly spirit.

The plane was dirty and the in seat air wasn't blowing as planes usually do.

Generally good but there wasn’t any staff available when my luggage didn’t appear at baggage claim in Fresno. It took about half an hour to locate a staff member to open up the locked room where it was being kept.

Do not like the feeling of being in the basic economy. Everyone should feel good no matter what.

All flights were on time and boarding was issue free

Left from gate 30 minutes before flight. Never been late to a flight ever. It says 15 minutes before explicitly on the ticket.

I like the boarding process, it was fast. The seat doesn’t have a TV for a long flight and food wasn’t served, just snacks.

Use planes with TVs on flights over 4 hours. The free entertainment was a cheap in between solution for a very long flight that you don't even bother providing meals or decent snacks.

Even though we left CMI late, we mostly made up the time.

Delayed almost 4 hours for a 45 minute flight with no explanation.

Again, multiple delays and I eventually just canceled and drove!

Great crew. Very comfortable business seats with nice bedding. Good food. We were delayed to let late passengers on the flight, but otherwise great experience.

Great crew. We were delayed so that late passengers could get on the flight. Love the bedding in business class. Good food. Great experience.

The CX617 from HK to BKK was delayed more than 1.5 hours.

Horrible - they lied to me about baggage & boarding, even though I specifically spoke to their agents the day before my flight about my issue. When I showed up they did not let me board and stranded me at my airport until I bought a new flight with money I did not have to spend.

Book cheap flights from Anchorage to Caribbean Islands

Recent round-trip flight deals

10/15Tue
2 stopsDelta
21h 27mANC-NAS
10/29Tue
2 stopsDelta
26h 18mNAS-ANC
$562
7/25Thu
3 stops
34h 46mANC-SJU
8/3Sat
2 stops
25h 42mSJU-ANC
$818
7/13Sat
2 stopsAmerican Airlines
19h 55mANC-SJU
7/17Wed
1 stopAmerican Airlines
20h 03mSJU-ANC
$833
10/20Sun
2 stopsDelta
18h 58mANC-NAS
10/27Sun
2 stopsDelta
23h 30mNAS-ANC
$847
10/6Sun
2 stopsDelta
22h 45mANC-SDQ
10/19Sat
2 stopsDelta
23h 01mSDQ-ANC
$853
7/25Thu
3 stops
34h 46mANC-SJU
8/2Fri
2 stops
20h 13mSJU-ANC
$866
10/14Mon
2 stopsAmerican Airlines
28h 53mANC-NAS
10/29Tue
2 stopsAmerican Airlines
15h 04mNAS-ANC
$907
5/22Wed
1 stopUnited Airlines
13h 43mANC-SJU
5/25Sat
1 stopUnited Airlines
12h 58mSJU-ANC
$923
5/22Wed
1 stopUnited Airlines
14h 02mANC-SJU
5/25Sat
2 stopsUnited Airlines
33h 38mSJU-ANC
$948
7/24Wed
2 stopsAlaska Airlines
22h 05mANC-SJU
8/2Fri
2 stopsAlaska Airlines
29h 36mSJU-ANC
$964

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Recent one-way flight deals

8/6Tue
2 stops
32h 08mANC-SJU
$368
7/19Fri
2 stops
25h 40mANC-SDQ
$375
7/14Sun
2 stops
25h 36mANC-SDQ
$376
7/26Fri
1 stopSun Country Air
14h 23mANC-SJU
$382
8/6Tue
2 stopsDelta
17h 54mANC-SJU
$421
7/3Wed
2 stopsDelta
20h 43mANC-SDQ
$467
8/5Mon
2 stopsAlaska Airlines
32h 19mANC-SJU
$477
8/6Tue
1 stopUnited Airlines
13h 11mANC-SJU
$631
8/6Tue
3 stopsUnited Airlines
21h 20mANC-SJU
$717
7/13Sat
2 stopsAmerican Airlines
37h 21mANC-SDQ
$781

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Last minute flights from Anchorage to Caribbean Islands

Last minute flight, train and bus deals

5/12Sun
multi-stopUnited Airlines
16h 53mANC-SJU
5/14Tue
multi-stopUnited Airlines
35h 28mSJU-ANC
$1,039
5/11Sat
multi-stopUnited Airlines
19h 32mANC-SJU
5/14Tue
multi-stopUnited Airlines
36h 23mSJU-ANC
$1,051
5/12Sun
multi-stopAmerican Airlines
12h 23mANC-SJU
5/13Mon
multi-stopAmerican Airlines
22h 12mSJU-ANC
$1,079
5/11Sat
multi-stopUnited Airlines
34h 17mANC-SJU
5/14Tue
multi-stopUnited Airlines
35h 28mSJU-ANC
$1,119
5/11Sat
multi-stopAmerican Airlines
17h 15mANC-SJU
5/13Mon
multi-stopAmerican Airlines
23h 46mSJU-ANC
$1,160
5/11Sat
multi-stopAmerican Airlines
17h 15mANC-SJU
5/13Mon
multi-stopAmerican Airlines
22h 12mSJU-ANC
$1,218

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Anchorage - Caribbean Islands Flights

Departure:

Anchorage (ANC)United States

Return flight deals:

Caribbean Islands - Anchorage

Cabin classes:

$254
$352
$282
$157