Winter break trips from Milwaukee
Where to go from Milwaukee 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).
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Where to go from Milwaukee
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 | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Punta Cana (PUJ) | Long white-sand beaches and easy all-inclusive resorts | No matching fare saved | Dec 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 year | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| San Juan (SJU) | Old San Juan, beaches and the rainforest, with no passport needed from the US | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Montego Bay (MBJ) | Jamaica's resort coast around Montego Bay and Negril | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Nassau (NAS) | Nassau and Paradise Island, a short flight from the East Coast | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Puerto Vallarta (PVR) | Puerto Vallarta's Pacific beaches and a walkable old town | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Los Cabos (SJD) | Los Cabos, desert coast, resorts and whale watching in winter | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Guanacaste (LIR) | Guanacaste's Pacific beaches in Costa Rica | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Oahu / Honolulu (HNL) | Waikiki and the North Shore on Oahu | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Maui / Kahului (OGG) | Maui's beaches, the Road to Hana and Haleakalā | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Orlando (MCO) | Orlando's theme parks | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Miami (MIA) | Miami Beach, warm water and a big food and nightlife scene | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Fort Lauderdale (FLL) | Fort Lauderdale beaches and an easy base for cruises | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Phoenix (PHX) | Phoenix and Scottsdale, warm and sunny all winter | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Palm Springs (PSP) | Palm Springs, desert sun, pools and mid-century style | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Denver (DEN) | Denver, the gateway to Vail, Breckenridge and Keystone | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Salt Lake City (SLC) | Salt Lake City, under an hour from a dozen ski resorts | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Jackson (JAC) | Jackson Hole, with steep terrain right next to the airport | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Vail (EGE) | Vail and Beaver Creek, about 35 miles from the airport | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| Vancouver (YVR) | Vancouver, about two hours from Whistler | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
| New York (JFK) | New York's holiday lights, windows and shows | No matching fare saved | Dec 19 – Dec 26, 2026 (suggested) | Search these dates |
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 Milwaukee. Winter break 2026 flights from Milwaukee: beaches, ski towns and cities, with fares for Christmas week and New Year's week.
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