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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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Calgary
From C$391 (US$276) round trip
19.1% below the middle price here: the cheapest return fare on each of 15 departure dates is usually C$391 (US$276) to C$619 (US$437).
This price is for these exact dates; other dates may cost more.
Cancun
From C$637 (US$450) round trip
16.2% 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 trip has 1 stop.
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Show all 10 places with recent prices from Winnipeg
| City | From | Dates | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| Calgary YYC | C$391 (US$276) | 8 Jan 2027 – 10 Jan 2027 · 2 nights | YWG → YYC | out nonstop, back nonstop | found yesterday | 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 |
| Cancun CUN | C$637 (US$450) | 28 Jan 2027 – 4 Feb 2027 · 7 nights | YWG → CUN | out 1 stop, back 1 stop | found today | See prices for these dates |
| Cartagena CTG | C$797 (US$563) | 18 Jan 2027 – 26 Jan 2027 · 8 nights | YWG → CTG | out 2 stops, back 2 stops | found today | See prices for these dates |
| San Jose SJO | C$841 (US$594) | 20 Jan 2027 – 30 Jan 2027 · 10 nights | YWG → SJO | out 2 stops, back 2 stops | found yesterday | See prices for these dates |
| Kauai Island LIH | C$1,257 (US$888) | 13 Jan 2027 – 28 Feb 2027 · 46 nights | YWG → LIH | out 1 stop, back 2 stops | found yesterday |
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