Winter break trips from Calgary
Where to go from Calgary 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.
Fares for Christmas week (Dec 19 – Dec 26, 2026) and New Year's week (Dec 26 – Jan 2, 2027) when saved; other dates are marked.
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Where to go from Calgary
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.
| Destination | Why go | Axel | Dates | |
|---|---|---|---|---|
| Cancun (CUN) | Caribbean beaches and the Hotel Zone, with Tulum and Playa del Carmen an hour or two south | Not priced yet | See flights | |
| Punta Cana (PUJ) | Long white-sand beaches and easy all-inclusive resorts | Not priced yet | See flights | |
| Aruba (AUA) | Dry, sunny and outside the hurricane belt, so it is a safe bet most of the year | Not priced yet | See flights | |
| San Juan (SJU) | Old San Juan, beaches and the rainforest, with no passport needed from the US | Not priced yet | See flights | |
| Montego Bay (MBJ) | Jamaica's resort coast around Montego Bay and Negril | Not priced yet | See flights | |
| Nassau (NAS) | Nassau and Paradise Island, a short flight from the East Coast | Not priced yet | See flights | |
| Puerto Vallarta (PVR) | Puerto Vallarta's Pacific beaches and a walkable old town | Not priced yet | See flights | |
| Los Cabos (SJD) | Los Cabos, desert coast, resorts and whale watching in winter | Not priced yet | See flights | |
| Guanacaste (LIR) | Guanacaste's Pacific beaches in Costa Rica | Not priced yet | See flights | |
| Oahu / Honolulu (HNL) | Waikiki and the North Shore on Oahu | Not priced yet | See flights | |
| Maui / Kahului (OGG) | Maui's beaches, the Road to Hana and Haleakalā | Not priced yet | See flights | |
| Orlando (MCO) | Orlando's theme parks | Not priced yet | See flights | |
| Miami (MIA) | Miami Beach, warm water and a big food and nightlife scene | Not priced yet | See flights | |
| Fort Lauderdale (FLL) | Fort Lauderdale beaches and an easy base for cruises | Not priced yet | See flights | |
| Phoenix (PHX) | Phoenix and Scottsdale, warm and sunny all winter | Not priced yet | See flights | |
| Palm Springs (PSP) | Palm Springs, desert sun, pools and mid-century style | Not priced yet | See flights | |
| Denver (DEN) | Denver, the gateway to Vail, Breckenridge and Keystone | Not priced yet | See flights | |
| Salt Lake City (SLC) | Salt Lake City, under an hour from a dozen ski resorts | Not priced yet | See flights | |
| Jackson (JAC) | Jackson Hole, with steep terrain right next to the airport | Not priced yet | See flights | |
| Vail (EGE) | Vail and Beaver Creek, about 35 miles from the airport | Not priced yet | See flights | |
| Vancouver (YVR) | Vancouver, about two hours from Whistler | Not priced yet | See flights | |
| New York (JFK) | New York's holiday lights, windows and shows | Not priced yet | See flights |
Keep exploring
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 Calgary. Winter break 2026 flights from Calgary: beaches, ski towns and cities, with fares for Christmas week and New Year's week.
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