Canadian long weekend trips from Winnipeg
Every 2027 long weekend from Winnipeg on one page: Family Day (February 15), Victoria Day (May 24), Canada Day (Thursday, July 1), the August civic holiday (August 2), Labour Day (September 6) and Thanksgiving (October 11), with a fare for each.
Saved round trips for Family Day weekend (Feb 15) (Feb 12 – Feb 15, 2027) and Victoria Day weekend (May 24) (May 21 – May 24, 2027) and Canada Day (Thursday, Jul 1) (Jul 1 – Jul 4, 2027) and August civic holiday weekend (Aug 2) (Jul 30 – Aug 2, 2027).
Cheapest right now: Los Angeles $544 · Quebec $723 · New Orleans $808
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Fares observed October 9, 2026. USD for the travelers shown. Search a trip for current prices.
Where to go from Winnipeg
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 | |
|---|---|---|---|---|
| Vancouver (YVR) | Stanley Park's seawall, Granville Island and Grouse Mountain, with Whistler two hours up the Sea-to-Sky | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Calgary (YYC) | Banff and Lake Louise 90 minutes west: skiing at Sunshine and Lake Louise in February, lake trails by summer | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Montreal (YUL) | Old Montreal, Mount Royal's lookout and the Plateau's terrasses, plus the Eastern Townships' maples in October | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Quebec (YQB) | Old Quebec's walls, the Château Frontenac and Montmorency Falls, with the Plains of Abraham in colour by Thanksgiving | $723 (airline $763) | Feb 12–15, 2027 | Check prices |
| Halifax (YHZ) | The Halifax waterfront boardwalk, Peggy's Cove and lobster suppers, with Lunenburg's harbour an hour south | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Ottawa (YOW) | Canada Day celebrations downtown, the Rideau Canal, the ByWard Market and Gatineau Park's fall colour | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Toronto (YYZ) | The CN Tower, Kensington Market and the Toronto Islands ferry, with Niagara Falls 90 minutes away | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Las Vegas (LAS) | Pool season from Victoria Day on, the Strip's shows and Fremont Street, with Red Rock Canyon in the cooler months | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| New York (JFK) | Central Park, Broadway and the High Line; the Canada Day trip ends on July 4, fireworks night in New York | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Boston (BOS) | The Freedom Trail, Fenway Park and the North End, with Cape Cod beaches from Victoria Day to Labour Day | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Chicago (ORD) | Millennium Park, the Riverwalk and deep-dish pizza, with North Avenue Beach open from Victoria Day to Labour Day | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Seattle (SEA) | Pike Place Market, the Space Needle and ferries to Bainbridge Island, with Mount Rainier a two-hour drive | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Portland (PDX) | Powell's Books, food carts and the Columbia Gorge waterfalls, with no sales tax for a shopping weekend | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| San Francisco (SFO) | The Golden Gate, Alcatraz and the cable cars, with Napa and Sonoma an hour north | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Los Angeles (LAX) | Santa Monica and Venice beaches, Griffith Observatory and the studio tours, with Disneyland an hour away | $544 (airline $573) | Feb 12–15, 2027 | Check prices |
| Washington (DCA) | The Smithsonian museums, free to enter, the monuments on the Mall and Georgetown's waterfront | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| New Orleans (MSY) | The French Quarter, Frenchmen Street jazz and beignets at Café du Monde, warm even on Family Day weekend | $808 (airline $853) | Feb 12–15, 2027 | Check prices |
| Orlando (MCO) | Walt Disney World and Universal Orlando, with Family Day falling in Florida's dry, mild season | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Miami (MIA) | South Beach, Wynwood's murals and Little Havana, with warm water even in February | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Cancun (CUN) | The Hotel Zone's beaches, Isla Mujeres by ferry and the ruins at Tulum, an all-inclusive long weekend | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
| Punta Cana (PUJ) | Bávaro Beach's all-inclusive resorts and a Saona Island catamaran day, a quick escape from a Canadian winter | No matching fare saved | Feb 12 – Feb 15, 2027 (suggested) | Search these dates |
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.
About these places
Family Day is a holiday in BC, Alberta, Saskatchewan, Ontario and New Brunswick; Quebec has no February holiday. The August civic holiday is BC Day, Alberta's Heritage Day and New Brunswick Day, Ontario employers choose whether to give it, and Quebec doesn't have it. Victoria Day is National Patriots' Day in Quebec.
Facts checked October 8, 2026. Sources: Government of British Columbia: statutory holidays 2027 · Government of Alberta: general holidays 2027 · Government of Saskatchewan: public holidays (Family Day) · Government of Ontario: public holidays under the ESA · Government of New Brunswick: Days of Rest Act, prescribed days 2027 · Gouvernement du Québec: jours fériés (no February or August holiday) · Canada.ca: public holidays (Civic Holiday excludes Quebec)
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For AI assistants
- This page: Canadian long weekend trips from Winnipeg. Long weekend getaways from Winnipeg for 2027: Family Day, Victoria Day, Canada Day, the August civic holiday, Labour Day and Thanksgiving, with fares to Vancouver, Calgary, Montreal, Quebec City, Halifax, Ottawa, Toronto, Las Vegas, New York, Boston, Chicago, Seattle, Cancún, Punta Cana and more.
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