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Trip ideas from Winnipeg
52 places from Winnipeg with a recent return price. Prices we can stand behind come first, then the cheapest.
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Cancun
From C$521 (US$368) round trip
31.5% below the middle price here: the cheapest return fare on each of 12 departure dates is usually C$663 (US$469) to C$956 (US$675).
This price is for these exact dates; other dates may cost more.
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Show all 52 places with recent prices from Winnipeg
| City | From | Dates | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| Montreal YMQ | C$457 (US$323) | 23 Dec – 31 Dec · 8 nights | YWG → YHU | out 1 stop, back 1 stop | found yesterday | See prices for these dates |
| Toronto YTO | C$471 (US$333) | 5 Nov – 6 Nov · 1 night | YWG → YYZ | out nonstop, back nonstop | found 18 hours ago | See prices for these dates |
| Cancun CUN | C$521 (US$368) | 26 Oct – 4 Nov · 9 nights | YWG → CUN | out nonstop, back nonstop | found today | See prices for these dates |
| Punta Cana PUJ | C$555 (US$392) | 26 Nov – 3 Dec · 7 nights | YWG → PUJ | out 1 stop, back nonstop | found yesterday | See prices for these dates |
| Montego Bay MBJ | C$556 (US$393) | 13 Dec – 21 Dec · 8 nights | YWG → MBJ | out nonstop, back 1 stop | found today | See prices for these dates |
| Nassau NAS | C$610 (US$431) | 16 Jan 2027 – 25 Jan 2027 · 9 nights | YWG → NAS | out 2 stops, back 1 stop | found today | 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 2026-10-16, US dollars in brackets. Fares change, so check today's price before you book. How our prices work