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San Jose

$197+ Cheap flights from Winnipeg (YWG) to San Jose, CA (SJC)

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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJC
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
1 adult, Economy
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Cheap flight deals from Winnipeg to San Jose

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 January 20, 2026.

This United Airlines deal was found by Cheapflights users on 1/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/102:20 pm
YWG
-
SJC
1 stop10h 39m
United Airlines
Thu 3/1210:55 pm
SJC
-
YWG
1 stop11h 02m
United Airlines
Deal found 1/18$339
This Delta deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:50 am
YWG
-
SJC
2 stops11h 27m
Delta
Sun 7/269:05 am
SJC
-
YWG
2 stops12h 22m
Delta
Deal found 1/19$382
This Delta deal was found by Cheapflights users on 1/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/106:40 am
YWG
-
SJC
2 stops17h 37m
Delta
Thu 3/126:00 am
SJC
-
YWG
2 stops10h 05m
Delta
Deal found 1/18$392
This WestJet deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:55 pm
YWG
-
SJC
2 stops28h 01m
WestJet
Fri 3/131:50 pm
SJC
-
YWG
2 stops26h 15m
WestJet
Deal found 1/20$405
This WestJet deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:00 am
YWG
-
SJC
2 stops14h 45m
WestJet
Sat 7/259:05 am
SJC
-
YWG
2 stops13h 25m
WestJet
Deal found 1/19$406
This WestJet deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 am
YWG
-
SJC
2 stops10h 53m
WestJet
Sun 7/269:05 am
SJC
-
YWG
2 stops13h 25m
WestJet
Deal found 1/19$431
This Delta deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:40 am
YWG
-
SJC
1 stop7h 29m
Delta
Fri 7/247:35 pm
SJC
-
YWG
2 stops13h 59m
Delta
Deal found 1/19$437
This Delta deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1412:40 pm
YWG
-
SJC
1 stop10h 13m
Delta
Fri 7/249:05 am
SJC
-
YWG
2 stops12h 22m
Delta
Deal found 1/19$462
This WestJet deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:00 am
YWG
-
SJC
2 stops10h 53m
WestJet
Sun 7/269:05 am
SJC
-
YWG
2 stops13h 25m
WestJet
Deal found 1/19$464
This Delta deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:40 pm
YWG
-
SJC
1 stop10h 13m
Delta
Sun 7/267:35 pm
SJC
-
YWG
2 stops13h 59m
Delta
Deal found 1/19$470

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 January 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$339
(United Airlines)

One-way from

$197
(Delta)
Provider with most accurate pricing for Winnipeg-San Jose flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-San Jose flights.
Search Deals
From Winnipeg to San Jose
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One-way flight from Winnipeg to San Jose
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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 2,558,603 searches. Data last updated January 20, 2026.
Use the filters below to find and compare flights from Winnipeg to San Jose that are best for you.

Fly from

Winnipeg

Fly to

San Jose

Route

Depart

Return

Price

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 3/10

2:20 pm-10:59 pm

1 stop10h 39m

San Jose

Thu 3/12

10:55 pm-11:57 am

1 stop11h 02m

$339

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Thu 7/16

8:50 am-6:17 pm

2 stops11h 27m

San Jose

Sun 7/26

9:05 am-11:27 pm

2 stops12h 22m

$382

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 3/10

6:40 am-10:17 pm

2 stops17h 37m

San Jose

Thu 3/12

6:00 am-6:05 pm

2 stops10h 05m

$392

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Fri 3/6

12:55 pm-2:56 pm

2 stops28h 01m

San Jose

Fri 3/13

1:50 pm-6:05 pm

2 stops26h 15m

$405

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 7/14

6:00 am-6:45 pm

2 stops14h 45m

San Jose

Fri 7/24

11:30 am-12:30 am

2 stops11h 00m

$406

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Thu 7/16

8:50 am-6:17 pm

2 stops11h 27m

San Jose

Sat 7/25

10:00 am-11:27 pm

2 stops11h 27m

$406

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Wed 7/15

12:40 pm-8:53 pm

1 stop10h 13m

San Jose

Sat 7/25

10:00 am-11:27 pm

2 stops11h 27m

$406

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Wed 7/15

6:00 am-2:53 pm

2 stops10h 53m

San Jose

Sun 7/26

9:05 am-12:30 am

2 stops13h 25m

$431

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 7/14

12:40 pm-8:53 pm

1 stop10h 13m

San Jose

Sat 7/25

10:00 am-11:27 pm

2 stops11h 27m

$431

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Thu 3/5

11:53 am-8:53 pm

1 stop11h 00m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 11 results
1
2
  • Most accurate provider: When it comes to deals on Winnipeg-San Jose, California flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-San Jose, California flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-San Jose, California flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Winnipeg-San Jose, California flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Winnipeg-San Jose, California flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, October is the cheapest month in which you can book a flight from Winnipeg to San Jose, California (average of $139). Flying from Winnipeg to San Jose, California in December is currently the most expensive (average of $217). 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?

    There are many flights that can get you from Winnipeg to San Jose, California in 10h 39m. Fly via United Airlines or Delta to get the fastest option. The distance between Winnipeg and San Jose, California is about 1496 mi. This flight may include one or multiple stops.

  • 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, October is the cheapest month in which you can book a flight from Winnipeg to San Jose, California (average of $139). Flying from Winnipeg to San Jose, California in December is currently the most expensive (average of $217). 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.

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