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Cheap flights from San Jose, CA to Winnipeg from C$ 288

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 27/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — YWG
26 Feb — 5 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from San Jose to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from San Jose to Winnipeg
Explore the most affordable flight options available from San Jose to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 27 January 2026.

Mon 13/79:05 a.m.
SJC
-
YWG
2 stops12h 22m
Delta
Thu 23/712:40 p.m.
YWG
-
SJC
1 stop10h 13m
Delta
Deal found 25/1C$ 664
Tue 3/39:15 a.m.
SJC
-
YWG
2 stops13h 26m
WestJet
Wed 4/310:55 a.m.
YWG
-
SJC
2 stops11h 24m
WestJet
Deal found 26/1C$ 712
Mon 26/18:05 p.m.
SJC
-
YWG
2 stops12h 58m
Delta
Wed 13/512:40 p.m.
YWG
-
SJC
1 stop10h 13m
Delta
Deal found 25/1C$ 2,005
Fri 1/58:45 a.m.
SJC
-
YWG
1 stop10h 12m
United Airlines
Mon 4/58:45 a.m.
YWG
-
SJC
1 stop6h 45m
United Airlines
Deal found 24/1C$ 2,087

Find flight deals from San Jose to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 27 January 2026.

Round-trip from

C$ 664

One-way from

C$ 288
Delta
  • Delta
  • 13/7-23/7
  • 3 total stops
  • 22h 35m total
  • San Jose to Winnipeg
Search Deals
WestJet
  • WestJet
  • 27/6
  • 2 total stops
  • 10h 25m total
  • San Jose to Winnipeg
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Jose to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 27 January 2026.
Use the filters below to find and compare flights from San Jose to Winnipeg that are best for you.

Fly from

San Jose

Fly to

Winnipeg

Route

Depart

Return

Price

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Mon 13/7

9:05 a.m.-11:27 p.m.

2 stops12h 22m

Winnipeg

Thu 23/7

12:40 p.m.-8:53 p.m.

1 stop10h 13m

C$ 664

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 3/3

9:15 a.m.-12:41 a.m.

2 stops13h 26m

Winnipeg

Wed 4/3

10:55 a.m.-8:19 p.m.

2 stops11h 24m

C$ 712

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Fri 1/5

8:45 a.m.-8:57 p.m.

1 stop10h 12m

Winnipeg

Mon 4/5

8:45 a.m.-1:30 p.m.

1 stop6h 45m

C$ 2,087

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sat 27/6

9:05 a.m.-9:30 p.m.

2 stops10h 25m

C$ 288

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Fri 26/6

10:56 p.m.-4:54 p.m.

2 stops15h 58m

C$ 296

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sat 27/6

9:05 a.m.-8:40 a.m.

3 stops21h 35m

C$ 490

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sat 27/6

7:00 a.m.-8:48 p.m.

1 stop11h 48m

C$ 579

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Fri 26/6

5:05 p.m.-11:40 a.m.

3 stops16h 35m

C$ 589

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Fri 26/6

6:30 p.m.-8:48 p.m.

1 stop24h 18m

C$ 1,376

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/1

Best time to book a flight from San Jose to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from San Jose with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from San Jose to Winnipeg

What is the cheapest month to book a flight from San Jose, California to Winnipeg?

Currently, March is the cheapest month in which you can book a flight from San Jose, California to Winnipeg (average of C$ 155). Flying from San Jose, California to Winnipeg in December is currently the most expensive (average of C$ 529). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from San Jose to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from San Jose, California to Winnipeg?

    A quick flight from San Jose, California to Winnipeg can take about 12h 22m. Delta provides one of the quickest options available for as low as C$ 664. San Jose, California and Winnipeg are separated by a distance of 2408 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • Can I find deals for flights from San Jose to Winnipeg that include hotel bookings?

    Yes. In addition to deals on San Jose to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Jose to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Jose to Winnipeg.

  • Can I find deals for business class flights from San Jose to Winnipeg?

    Yes. Cheapflights offers flight deals from San Jose to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San Jose, California to Winnipeg?

    Currently, March is the cheapest month in which you can book a flight from San Jose, California to Winnipeg (average of C$ 155). Flying from San Jose, California to Winnipeg in December is currently the most expensive (average of C$ 529). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Selkirk
Portage la Prairie

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Can Cheapflights find flights from San Jose to Winnipeg with no change fees?

Yes! Cheapflights helps users easily find flights from San Jose to Winnipeg with no change fees.

Can Cheapflights notify me if prices for flights from San Jose to Winnipeg become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Winnipeg from San Jose today and book when prices fit your budget.

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