Flights from Anchorage to the Caribbean for a week

A week opens up the smaller islands: St. Lucia, Antigua, Turks and Caicos and Grand Cayman are worth the connection, and Punta Cana or Montego Bay stay the easy nonstop choice. December to April is dry season; June to November is hurricane season, and Aruba, Curaçao and Barbados sit mostly outside it.

One stop via Denver: Punta Cana; via Chicago: Montego Bay, Nassau, Aruba, San Juan, Grand Cayman Island, Saint Thomas and Sint Maarten. No nonstop seen to Providenciales, Curacao, Bridgetown, Saint Lucia, Antigua, Kingston, Santo Domingo and Saint Croix on the dates searched recently.

Where to fly from Anchorage to the Caribbean for a week: round trips of 6 to 8 nights to Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more. Pick a destination to see every date, or search your own dates in one tap.

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The cheapest matching round trip we’ve seen recently for each destination.

Cheapest right now: San Juan $819 · Nassau $868 · Montego Bay $976

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Flights from Anchorage

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The Caribbean for a week from other cities

Fares observed October 24 – 28, 2026. USD for the travelers shown. Search a trip for current prices.

Where to go from Anchorage

Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.

DestinationWhy goFlightsAxelDates
Punta Cana (PUJ)Punta Cana's long white-sand beaches and all-inclusive resorts1 stop via Denver$1,205 (airline $1,275)Jun 19–26, 2027Check prices
Montego Bay (MBJ)Jamaica's resort coast around Montego Bay and Negril1 stop via Chicago$976 (airline $1,033)Jun 5–12, 2027Check prices
Nassau (NAS)Nassau and Paradise Island, a short flight from the East Coast1 stop via Chicago$868 (airline $915)Jun 5–12, 2027Check prices
Aruba (AUA)Aruba's dry, sunny weather outside the hurricane belt1 stop via Chicago$1,027 (airline $1,084)Jan 12–19, 2027Check prices
San Juan (SJU)Old San Juan, beaches and the rainforest, no passport needed from the US1 stop via Chicago$819 (airline $865)Jan 12–19, 2027Check prices
Grand Cayman Island (GCM)Seven Mile Beach and world-class diving on Grand Cayman1 stop via Chicago$1,056 (airline $1,112)Jan 12–19, 2027Check prices
Providenciales (PLS)Grace Bay in Turks and Caicos, one of the Caribbean's best-known beachesNo nonstop seen$1,122 (airline $1,187)Nov 14–21, 2026Check prices
Saint Thomas (STT)St. Thomas beaches and an easy ferry to St. John, no passport needed from the US1 stop via Chicago$982 (airline $1,034)Dec 8–15, 2026Check prices
Sint Maarten (SXM)St. Martin, two countries on one island with plenty of beaches1 stop via Chicago$996 (airline $1,052)Dec 8–15, 2026Check prices
Curacao (CUR)Curaçao's calm coves for snorkelling and colourful WillemstadNo nonstop seen$1,140 (airline $1,202)Jan 12–19, 2027Check prices
Bridgetown (BGI)Barbados beaches on the calm west coast and surf on the eastNo nonstop seen$1,161 (airline $1,224)Nov 10–17, 2026Check prices
Saint Lucia (UVF)St. Lucia's Pitons, rainforest and resort beachesNo nonstop seen$1,317 (airline $1,389)Dec 8–15, 2026Check prices
Antigua (ANU)Antigua, a beach for every day of the yearNo nonstop seen$1,422 (airline $1,502)Nov 10–17, 2026Check prices
Kingston (KIN)Kingston, Jamaica's capital, with the Blue Mountains nearbyNo nonstop seen$1,266 (airline $1,335)Nov 10–17, 2026Check prices
Santo Domingo (SDQ)Santo Domingo's colonial zone, the oldest city in the AmericasNo nonstop seenNo matching fare savedSearch other dates
Saint Croix (STX)St. Croix's beaches, rum distilleries and Danish-era towns, no passport needed from the USNo nonstop seen$1,109 (airline $1,169)Nov 10–17, 2026Check prices

The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.

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Hotels in Punta Cana with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Punta Cana has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

Where to stay: Where to stay in Punta Cana: the 7 best neighborhoods, ranked · Punta Cana hotels where a family of four can share one room

Hotels with an Axel review in Punta Cana: Punta Cana Seven Beaches · Flor Del Mar Condo · Dreams Flora Resort & Spa · whala!urban punta cana · AC Hotel by Marriott Punta Cana · All 82 reviewed hotels in Punta Cana

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  • This page: Flights from Anchorage to the Caribbean for a week. Round-trip fares from Anchorage to the Caribbean for a week: Punta Cana, Montego Bay, Nassau, Aruba, San Juan and Grand Cayman Island and more, for stays of 6 to 8 nights. The cheapest saved fare for each destination, and a link to search your own dates.
  • Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.
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