Cheap flights from Winnipeg

We are watching 42 routes out of Winnipeg. The cheapest fare we can vouch for today is €106, and for each one we say whether today is a good moment or you should wait.

See this fare · Vancouver €106 Calgary €110 Penticton €124

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Where to fly from Winnipeg

Fri

22 Jan

Winnipeg → Vancouver

WestJet Based on 345 observations 2 stops

WestJet Based on 172 observations 1 stop

WestJet Based on 21 observations 1 stop

WestJet Based on 103 observations 1 stop

WestJet Based on 26 observations 1 stop

WestJet Based on 39 observations 1 stop

WestJet Based on 54 observations 1 stop

WestJet Based on 29 observations ✈ Direct

WestJet Based on 10 observations 2 stops

Air Canada Based on 128 observations 2 stops

WestJet Based on 51 observations 2 stops

€201

Tue

1 Dec

Winnipeg → Philadelphia

WestJet Based on 20 observations 2 stops

€204

Tue

17 Nov

Winnipeg → Puerto Vallarta

WestJet Based on 51 observations 1 stop

WestJet Based on 29 observations ✈ Direct

€207

Wed

6 Jan

Winnipeg → Pittsburgh

WestJet Based on 11 observations 3 stops

WestJet Based on 25 observations 1 stop

WestJet Based on 23 observations 3 stops

WestJet Based on 10 observations 2 stops

WestJet Based on 25 observations 2 stops

€240

Sat

28 Nov

Winnipeg → Punta Cana

Air Canada Based on 29 observations 1 stop

WestJet Based on 14 observations 2 stops

WestJet Based on 15 observations 2 stops

WestJet Based on 18 observations 2 stops

WestJet Based on 36 observations 3 stops

WestJet Based on 29 observations 2 stops

Porter Airlines Canada Based on 16 observations 1 stop

Flair Airlines Based on 116 observations 2 stops

WestJet Based on 88 observations 2 stops

WestJet Based on 81 observations 2 stops

WestJet Based on 15 observations 2 stops

WestJet Based on 12 observations 2 stops

€296

Sat

14 Nov

Winnipeg → Mexico City

Air Canada Based on 26 observations 2 stops

WestJet Based on 73 observations 3 stops

€318

Tue

17 Nov

Winnipeg → Thunder Bay

Flair Airlines Based on 31 observations 1 stop

WestJet Based on 10 observations 2 stops

Porter Airlines Canada Based on 8 observations 1 stop

€334

Thu

12 Nov

Winnipeg → Los Angeles

WestJet Based on 21 observations 1 stop

€344

Sat

14 Nov

Winnipeg → Prince George

WestJet Based on 28 observations 2 stops

€356

Tue

10 Nov

Winnipeg → Whitehorse

WestJet Based on 20 observations 3 stops

WestJet Based on 22 observations 3 stops

WestJet Based on 59 observations 3 stops

WestJet Based on 21 observations 3 stops

€387

Flights from Winnipeg: quick answers

What is the cheapest flight from Winnipeg right now?

Vancouver at €106 one-way, the lowest fare today across the 42 routes we track from Winnipeg. Next: Calgary €110, Penticton €124, Ottawa €131.

What is the cheapest month to fly from Winnipeg?

November. On the 23 routes from Winnipeg where we measured it, November fares were typically 7% below the route's median month.

How far in advance should I book flights from Winnipeg?

0–13 days before departure: that has been the cheapest booking window on 16 of the 33 routes from Winnipeg where we measured it.

Which airlines have the cheapest flights from Winnipeg?

WestJet has the lowest fare on 35 of the 42 routes we track from Winnipeg, then Air Canada (3), Porter Airlines Canada (2), Flair Airlines (2).

How many routes from Winnipeg does Piratefly track?

42 routes, with 1,960 fares we have recorded over time.

Booking tips from our fare data

How far in advance should you book a flight?: Book 1–1.5 months before departure. Tracking the same flights at every lead time (100,526 flights on 20,292 routes, 2026-06-14 to 2026-11-06), that window had the smallest average premium over each flight's lowest fare: +16.6%, against +49.1% in the last 3 days.
What is the cheapest day of the week to fly?: Wednesday. Comparing each fare with the median of its own route, Wednesday departures were +3.5% and Tuesday +4.4%, while Friday was the dearest at +10.4%. Weekend departures cost more than midweek ones.
What is the cheapest month to fly?: November 2026. Comparing each route's fares month by month (booked 8–60 days ahead), November 2026 departures were -1.2% against the route's own median, while January 2027 was the dearest at +25.4%. Covers September 2026, October 2026, November 2026, December 2026, January 2027; fares observed 2026-06-14 to 2026-11-06.