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San Jose

$154+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJC
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Winnipeg to San Jose

Best flights from Winnipeg to San Jose
Discover carefully curated flight deals from Winnipeg to San Jose that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 12, 2025.

This Delta deal was found by Cheapflights users on 12/10. 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 2/2611:53 amYWG - SJC
1 stop11h 00mDelta
Sat 3/710:30 pmSJC - YWG
1 stop13h 39mDelta
Deal found 12/10$430
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:30 amYWG - SJC
1 stop12h 24mMultiple Airlines
Sat 3/72:36 pmSJC - YWG
2 stops20h 16mMultiple Airlines
Deal found 12/10$436
This WestJet deal was found by Cheapflights users on 12/9. 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.
Mon 1/124:10 pmYWG - SJC
2 stops32h 02mWestJet
Wed 1/149:15 amSJC - YWG
2 stops11h 26mWestJet
Deal found 12/9$445
This Delta deal was found by Cheapflights users on 12/10. 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.
Sat 2/286:15 amYWG - SJC
2 stops17h 25mDelta
Sat 3/710:30 pmSJC - YWG
1 stop13h 39mDelta
Deal found 12/10$443
This Justfly.com deal was found by Cheapflights users on 12/10. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:55 amYWG - SJC
2 stops40h 24mWestJet
Sat 3/77:15 amSJC - YWG
2 stops27h 37mWestJet
Deal found 12/10$456
This American Airlines deal was found by Cheapflights users on 12/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2812:10 pmYWG - SJC
3 stops24h 01mAmerican Airlines
Sat 3/74:22 pmSJC - YWG
3 stops28h 13mAmerican Airlines
Deal found 12/10$1,129
This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:15 amYWG - SJC
2 stops10h 41mWestJet
Sat 3/77:15 amSJC - YWG
2 stops15h 25mWestJet
Deal found 12/10$514
This Delta deal was found by Cheapflights users on 12/11. 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.
Mon 1/1211:53 amYWG - SJC
1 stop11h 35mDelta
Wed 1/146:20 amSJC - YWG
1 stop8h 09mDelta
Deal found 12/11$971

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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$430
(Delta)

One-way from

$154
(Trip.com)
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
Search Deals
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 December 12, 2025.
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

Thu 2/26

11:53 am-8:53 pm

1 stop11h 00m

San Jose

Sat 3/7

10:30 pm-2:09 pm

1 stop13h 39m

$430

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Thu 2/26

7:30 am-5:54 pm

1 stop12h 24m

San Jose

Sat 3/7

2:36 pm-12:52 pm

2 stops20h 16m

$436

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Sat 2/28

6:15 am-9:40 pm

2 stops17h 25m

San Jose

Sat 3/7

10:30 pm-2:09 pm

1 stop13h 39m

$443

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Mon 1/12

4:10 pm-10:12 pm

2 stops32h 02m

San Jose

Wed 1/14

9:15 am-10:41 pm

2 stops11h 26m

$445

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Thu 2/26

5:55 am-8:19 pm

2 stops40h 24m

San Jose

Sat 3/7

7:15 am-12:52 pm

2 stops27h 37m

$456

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Sat 2/28

6:15 am-2:56 pm

2 stops10h 41m

San Jose

Sat 3/7

7:15 am-12:40 am

2 stops15h 25m

$514

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Mon 1/12

11:53 am-9:28 pm

1 stop11h 35m

San Jose

Wed 1/14

6:20 am-4:29 pm

1 stop8h 09m

$971

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Sat 2/28

12:10 pm-10:11 am

3 stops24h 01m

San Jose

Sat 3/7

4:22 pm-10:35 pm

3 stops28h 13m

$1,129

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Wed 1/21

4:10 pm-11:39 am

2 stops21h 29m

$154

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Wed 3/18

2:20 pm-10:59 pm

1 stop10h 39m

$204

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 16 results
1
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Compare providers for flights from Winnipeg to San Jose

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Winnipeg to San Jose in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Winnipeg-San Jose, California flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Winnipeg-San Jose, California flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 $222). 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 11h. Fly via Delta or WestJet 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 $222). 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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