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Flights from San Jose to Winnipeg
There are no direct flights from San Jose to Winnipeg. The easiest way is one stop via Toronto or Montreal, about 9h 06m door to door.
No direct flights · 6 connection options From 9h 06m
San Jose to Winnipeg at a glance
Fastest journey9h 06mEstimated
Nonstop flightsNoneConnect via Toronto or Montreal
Best ways to fly from San Jose to Winnipeg
Ranked by how easy the connection is: one airline or alliance first (bags and connection protected), then the quickest self-transfer options.
1Search
SJO Toronto (YYZ) YWG
Leg 1: Air Canada, Air Transat · Leg 2: Air Canada, Flair Airlines, Porter Airlines
4Search
SJO Chicago (ORD) YWG
Leg 1: American Airlines, Avianca Costa Rica, United Airlines · Leg 2: SkyWest
5Search
SJO Orlando (MCO) YWG
Leg 1: Frontier Airlines, Southwest Airlines, Volaris Costa Rica · Leg 2: WestJet
Connections are computed from flights actually flown over the last 8 weeks, with at least 45 minutes to change on one airline and 2 hours on separate tickets. Times are local. The search shows live itineraries and exact times.
Good to know
- Distance
- 4,604 km2,859 miles
- Journey time
- 9h 06mestimate
- Time difference
- NoneWinnipeg vs San Jose
- Currency in Winnipeg
- CAD
- Airports
- SJO → YWG
Flights from San Jose to Winnipeg: questions answered
Are there direct flights from San Jose to Winnipeg?
No. There is no nonstop service, so you will connect, most easily in Toronto, Montreal and Cancun. Some connections are on one airline or alliance, so your bags and connection are protected on a single ticket.
How long is the flight from San Jose to Winnipeg?
With one connection the journey usually takes around 9h 06m, depending on the layover. The straight-line distance is 4,604 km.
Where do you change planes between San Jose and Winnipeg?
The best connecting points are Toronto (YYZ), Montreal (YUL), Cancun (CUN) and Chicago (ORD). Air Canada flies both legs via Toronto, so you can book it as one ticket.
Which airports serve San Jose and Winnipeg?
San Jose: Juan Santamaría International Airport (SJO). Winnipeg: Winnipeg / James Armstrong Richardson International Airport (YWG).





