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Cheap flights from Winnipeg to San Jose, CA from C$ 323

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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJC
28 Mar — 4 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to San Jose

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to San Jose
Explore the most affordable flight options available from Winnipeg to San Jose. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 26 February 2026.

Wed 1/42:00 p.m.
YWG
-
SJC
1 stop10h 36m
United Airlines
Tue 7/43:45 p.m.
SJC
-
YWG
2 stops18h 07m
United Airlines
Deal found 22/2C$ 463
Wed 1/46:15 a.m.
YWG
-
SJC
2 stops17h 47m
WestJet
Tue 7/43:37 p.m.
SJC
-
YWG
2 stops24h 28m
WestJet
Deal found 22/2C$ 553
Tue 10/32:20 p.m.
YWG
-
SJC
1 stop10h 39m
United Airlines
Thu 12/310:55 p.m.
SJC
-
YWG
1 stop11h 02m
United Airlines
Deal found 22/2C$ 568
Tue 10/311:55 a.m.
YWG
-
SJC
2 stops14h 03m
Delta
Thu 12/36:00 a.m.
SJC
-
YWG
2 stops10h 05m
Delta
Deal found 23/2C$ 849
Tue 10/36:15 a.m.
YWG
-
SJC
2 stops10h 24m
WestJet
Thu 12/39:15 a.m.
SJC
-
YWG
2 stops30h 50m
WestJet
Deal found 24/2C$ 903
Wed 1/48:20 p.m.
YWG
-
SJC
3 stops23h 11m
Multiple Airlines
Tue 7/43:37 p.m.
SJC
-
YWG
3 stops31h 02m
Multiple Airlines
Deal found 22/2C$ 927

Find flight deals from Winnipeg to San Jose

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to San Jose (SJC). 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 26 February 2026.

Round-trip from

C$ 463

One-way from

C$ 323
United Airlines
  • United Airlines
  • 1/4-7/4
  • 3 total stops
  • 28h 43m total
  • Winnipeg to San Jose
Search Deals
10/4
  • 10/4
  • 3 total stops
  • 44h 51m total
  • Winnipeg to San Jose
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to San Jose 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 26 February 2026.
Use the filters below to find and compare flights from Winnipeg to San Jose that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Wed 1/4

2:00 p.m.-10:36 p.m.

1 stop10h 36m

San Jose

Tue 7/4

3:45 p.m.-11:52 a.m.

2 stops18h 07m

C$ 463

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 10/3

2:20 p.m.-10:59 p.m.

1 stop10h 39m

San Jose

Thu 12/3

10:55 p.m.-11:57 a.m.

1 stop11h 02m

C$ 568

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 10/3

11:55 a.m.-11:58 p.m.

2 stops14h 03m

San Jose

Thu 12/3

6:00 a.m.-6:05 p.m.

2 stops10h 05m

C$ 849

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 10/3

6:15 a.m.-2:39 p.m.

2 stops10h 24m

San Jose

Thu 12/3

9:15 a.m.-6:05 p.m.

2 stops30h 50m

C$ 903

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Wed 1/4

8:20 p.m.-5:31 p.m.

3 stops23h 11m

San Jose

Tue 7/4

3:37 p.m.-12:41 a.m.

2 stops31h 04m

C$ 937

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Fri 10/4

4:10 p.m.-11:01 a.m.

3 stops44h 51m

C$ 323

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Fri 10/4

6:40 a.m.-10:18 p.m.

2 stops17h 38m

C$ 367

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Fri 10/4

8:45 a.m.-1:35 p.m.

1 stop6h 50m

C$ 453

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/2

Sorted by cheapest first

Best time to book a flight from Winnipeg to San Jose

Have a flexible travel schedule? Discover the best time to fly to San Jose from Winnipeg 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 Winnipeg to San Jose

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

Currently, January is the cheapest month in which you can book a flight from Winnipeg to San Jose, California (average of C$ 166). Flying from Winnipeg to San Jose, California in February is currently the most expensive (average of C$ 345). 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 Winnipeg to San Jose. 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 Winnipeg to San Jose, California?

    United Airlines and Delta can get you from Winnipeg to San Jose, California in just under 10h 36m. Your travel time can differ by up to 3h 27m. There are 2408 km between Winnipeg and San Jose, California. Both multi-stop and direct flights can be found to your destination and back.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Winnipeg to San Jose 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 Winnipeg to San Jose, California?

    Currently, January is the cheapest month in which you can book a flight from Winnipeg to San Jose, California (average of C$ 166). Flying from Winnipeg to San Jose, California in February is currently the most expensive (average of C$ 345). 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

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How does Cheapflights help users find flights from Winnipeg to San Jose?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Winnipeg to San Jose. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to San Jose?

Cheapflights helps you find that perfect flight to San Jose from Winnipeg by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

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

Yes, we can. To see specific flights from Winnipeg to San Jose with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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

Yes, Cheapflights offers price alerts on Winnipeg to San Jose flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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