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Cheap flights from Winnipeg to San Jose, CA from C$ 264

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 31/3. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJC
16 Mar — 23 Mar1
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 14 February 2026.

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 10/2C$ 453
Tue 10/34:10 p.m.
YWG
-
SJC
2 stops24h 29m
WestJet
Thu 12/33:37 p.m.
SJC
-
YWG
2 stops29h 03m
WestJet
Deal found 12/2C$ 576
Tue 10/311:55 a.m.
YWG
-
SJC
1 stop10h 29m
Delta
Thu 12/37:15 a.m.
SJC
-
YWG
2 stops25h 46m
Delta
Deal found 11/2C$ 674
Thu 8/106:00 a.m.
YWG
-
SJC
2 stops10h 52m
WestJet
Sun 11/109:05 a.m.
SJC
-
YWG
2 stops11h 05m
WestJet
Deal found 14/2C$ 696
Sun 22/211:53 a.m.
YWG
-
SJC
1 stop11h 00m
Delta
Fri 27/26:30 p.m.
SJC
-
YWG
2 stops14h 31m
Delta
Deal found 11/2C$ 843
Sat 21/26:00 a.m.
YWG
-
SJC
2 stops17h 12m
Air Canada
Sat 28/23:55 p.m.
SJC
-
YWG
2 stops19h 04m
Air Canada
Deal found 14/2C$ 1,114
Sat 21/26:15 a.m.
YWG
-
SJC
2 stops17h 50m
WestJet
Sat 28/211:45 a.m.
SJC
-
YWG
2 stops8h 55m
WestJet
Deal found 14/2C$ 1,130
Tue 17/22:40 p.m.
YWG
-
SJC
2 stops28h 58m
WestJet
Sat 28/27:15 a.m.
SJC
-
YWG
2 stops15h 25m
WestJet
Deal found 14/2C$ 1,174

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 14 February 2026.

Round-trip from

C$ 453

One-way from

C$ 264
United Airlines
  • United Airlines
  • 10/3-12/3
  • 2 total stops
  • 21h 41m total
  • Winnipeg to San Jose
Search Deals
Delta
  • Delta
  • 31/3
  • 2 total stops
  • 8h 38m 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 14 February 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 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$ 453

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 10/3

4:10 p.m.-2:39 p.m.

2 stops24h 29m

San Jose

Thu 12/3

3:37 p.m.-10:40 p.m.

2 stops29h 03m

C$ 576

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 10/3

11:55 a.m.-8:24 p.m.

1 stop10h 29m

San Jose

Thu 12/3

7:15 a.m.-11:01 a.m.

2 stops25h 46m

C$ 674

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 31/3

5:20 p.m.-11:58 p.m.

2 stops8h 38m

C$ 264

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Sat 18/4

11:55 a.m.-7:01 p.m.

2 stops9h 06m

C$ 271

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 31/3

4:10 p.m.-11:46 a.m.

3 stops21h 36m

C$ 300

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Mon 23/3

5:55 a.m.-5:31 p.m.

2 stops37h 36m

C$ 344

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Sun 22/3

2:40 p.m.-7:41 p.m.

2 stops31h 01m

C$ 383

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Mon 23/3

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

1 stop10h 39m

C$ 410

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Sun 22/3

11:55 a.m.-8:24 p.m.

1 stop10h 29m

C$ 410

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/2

Showing 1-10 of 11 results
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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$ 165). Flying from Winnipeg to San Jose, California in February is currently the most expensive (average of C$ 343). 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 WestJet can get you from Winnipeg to San Jose, California in just under 10h 39m. Your travel time can differ by up to 13h 50m. 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$ 165). Flying from Winnipeg to San Jose, California in February is currently the most expensive (average of C$ 343). 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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