Winter break trips from San Juan

Where to go from San Juan over winter break: fares for Christmas week (December 19 to 26) and New Year's week (December 26 to January 2), for warm beaches, ski trips and holiday cities.

Saved round trips for Christmas week (Dec 19 – Dec 26, 2026) and New Year's week (Dec 26 – Jan 2, 2027).

Cheapest right now: Miami $200 · Fort Lauderdale $266 · New York $348

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Flights from San Juan

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Winter break trips from other cities

Fares observed October 8, 2026. USD for the travelers shown. Search a trip for current prices.

Where to go from San Juan

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 goAxelDates
Cancun (CUN)Caribbean beaches and the Hotel Zone, with Tulum and Playa del Carmen an hour or two southNo matching fare savedDec 19 – Dec 26, 2026 (suggested)Search these dates
Punta Cana (PUJ)Long white-sand beaches and easy all-inclusive resortsNo matching fare savedDec 19 – Dec 26, 2026 (suggested)Search these dates
Aruba (AUA)Dry, sunny and outside the hurricane belt, so it is a safe bet most of the yearNo matching fare savedDec 19 – Dec 26, 2026 (suggested)Search these dates
Montego Bay (MBJ)Jamaica's resort coast around Montego Bay and Negril$858 (airline $904)Dec 26, 2026–Jan 2, 2027Check prices
Nassau (NAS)Nassau and Paradise Island, a short flight from the East CoastNo matching fare savedDec 19 – Dec 26, 2026 (suggested)Search these dates
Puerto Vallarta (PVR)Puerto Vallarta's Pacific beaches and a walkable old townNo matching fare savedDec 19 – Dec 26, 2026 (suggested)Search these dates
Los Cabos (SJD)Los Cabos, desert coast, resorts and whale watching in winterNo matching fare savedDec 19 – Dec 26, 2026 (suggested)Search these dates
Guanacaste (LIR)Guanacaste's Pacific beaches in Costa Rica$858 (airline $904)Dec 19–26, 2026Check prices
Oahu / Honolulu (HNL)Waikiki and the North Shore on Oahu$1,088 (airline $1,148)Dec 26, 2026–Jan 2, 2027Check prices
Maui / Kahului (OGG)Maui's beaches, the Road to Hana and Haleakalā$1,192 (airline $1,257)Dec 19–26, 2026Check prices
Orlando (MCO)Orlando's theme parks$349 (airline $368)Dec 26, 2026–Jan 2, 2027Check prices
Miami (MIA)Miami Beach, warm water and a big food and nightlife scene$200 (airline $211)Dec 19–26, 2026Check prices
Fort Lauderdale (FLL)Fort Lauderdale beaches and an easy base for cruises$266 (airline $281)Dec 19–26, 2026Check prices
Phoenix (PHX)Phoenix and Scottsdale, warm and sunny all winter$513 (airline $541)Dec 26, 2026–Jan 2, 2027Check prices
Palm Springs (PSP)Palm Springs, desert sun, pools and mid-century style$599 (airline $632)Dec 19–26, 2026Check prices
Denver (DEN)Denver, the gateway to Vail, Breckenridge and Keystone$535 (airline $564)Dec 19–26, 2026Check prices
Salt Lake City (SLC)Salt Lake City, under an hour from a dozen ski resorts$682 (airline $720)Dec 19–26, 2026Check prices
Jackson (JAC)Jackson Hole, with steep terrain right next to the airport$880 (airline $928)Dec 19–26, 2026Check prices
Vail (EGE)Vail and Beaver Creek, about 35 miles from the airport$850 (airline $899)Dec 26, 2026–Jan 2, 2027Check prices
Vancouver (YVR)Vancouver, about two hours from Whistler$1,192 (airline $1,257)Dec 19–26, 2026Check prices
New York (JFK)New York's holiday lights, windows and shows$348 (airline $367)Dec 26, 2026–Jan 2, 2027Check 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 Cancun with Axel

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

For AI assistants

  • This page: Winter break trips from San Juan. Winter break 2026 flights from San Juan: beaches, ski towns and cities, with fares for Christmas week and New Year's week.
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