Trip ideas from Winnipeg

58 places from Winnipeg with a recent return price. Prices we can stand behind come first, then the cheapest.

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Show all 26 places with recent prices from Winnipeg

The cheapest recent price for each place — per traveler in Economy.

City	From	Dates	Airports	Stops	Found
Ontario ONT	C$1,012 (US$710)	23 Dec – 2 Jan 2027 · 10 nights	YWG → ONT	out 2 stops, back 2 stops	found yesterday	See prices for these dates
Toronto YTO	C$222 (US$156)	3 Dec – 5 Dec · 2 nights	YWG → YYZ	out nonstop, back nonstop	found 2 days ago	See prices for these dates
Ottawa YOW	C$341 (US$239)	1 Dec – 1 Dec	YWG → YOW	out nonstop, back 1 stop	found 2 days ago	See prices for these dates
Montreal YMQ	C$450 (US$316)	21 Dec – 25 Dec · 4 nights	YWG → YHU	out 1 stop, back 1 stop	found 3 days ago	See prices for these dates
Montego Bay MBJ	C$663 (US$465)	13 Dec – 21 Dec · 8 nights	YWG → MBJ	out nonstop, back 2 stops	found 2 days ago	See prices for these dates
San Salvador SAL	C$1,142 (US$801)	26 Dec – 9 Feb 2027 · 45 nights	YWG → SAL	out 2 stops, back 2 stops	found 2 days ago	See prices for these dates
Punta Cana PUJ	C$1,349 (US$946)	20 Dec – 2 Jan 2027 · 13 nights	YWG → PUJ	out 1 stop, back nonstop	found 2 days ago	See prices for these dates

Prices are what travelers' searches on Aviasales found in the last 7 days: the price the seller showed on Aviasales; bags may cost extra. Canadian dollars at the Bank of Canada rate of 2026-11-12, US dollars in brackets. Fares change, so check today's price before you book. How our prices work