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Cheap flights from Winnipeg to San Jose, CA from C$ 339

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 16/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJC
2 May — 9 May1
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 2 April 2026.

Sat 25/46:15 a.m.
YWG
-
SJC
2 stops10h 53m
WestJet
Tue 28/410:10 a.m.
SJC
-
YWG
2 stops29h 15m
WestJet
Deal found 29/3C$ 521
Tue 5/510:10 a.m.
YWG
-
SJC
2 stops13h 51m
WestJet
Wed 6/510:10 a.m.
SJC
-
YWG
2 stops29h 15m
WestJet
Deal found 30/3C$ 545
Tue 21/412:55 p.m.
YWG
-
SJC
2 stops28h 13m
WestJet
Thu 23/44:00 p.m.
SJC
-
YWG
2 stops28h 40m
WestJet
Deal found 29/3C$ 553
Tue 12/54:55 p.m.
YWG
-
SJC
2 stops24h 37m
WestJet
Tue 19/52:51 p.m.
SJC
-
YWG
2 stops24h 34m
WestJet
Deal found 28/3C$ 567
Tue 7/77:00 a.m.
YWG
-
SJC
2 stops10h 47m
WestJet
Sat 11/77:00 a.m.
SJC
-
YWG
2 stops15h 55m
WestJet
Deal found 30/3C$ 607
Thu 17/96:00 a.m.
YWG
-
SJC
2 stops10h 53m
WestJet
Mon 21/97:15 a.m.
SJC
-
YWG
2 stops8h 10m
WestJet
Deal found 1/4C$ 611
Sat 25/48:45 a.m.
YWG
-
SJC
1 stop14h 22m
United Airlines
Tue 28/48:45 a.m.
SJC
-
YWG
2 stops25h 07m
United Airlines
Deal found 31/3C$ 614
Tue 12/511:55 a.m.
YWG
-
SJC
1 stop10h 43m
Delta
Tue 19/58:50 p.m.
SJC
-
YWG
2 stops12h 04m
Delta
Deal found 28/3C$ 650

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 2 April 2026.

Round-trip from

C$ 521

One-way from

C$ 339
WestJet
  • WestJet
  • 25/4-28/4
  • 4 total stops
  • 40h 08m total
  • Winnipeg to San Jose
Search Deals
16/5
  • 16/5
  • 3 total stops
  • 44h 34m 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 2 April 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

Cheapest round-trip

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 21/4

12:55 p.m.-3:08 p.m.

2 stops28h 13m

San Jose

Thu 23/4

4:00 p.m.-10:40 p.m.

2 stops28h 40m

C$ 553
Quickest round-trip

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Thu 17/9

6:00 a.m.-2:53 p.m.

2 stops10h 53m

San Jose

Mon 21/9

7:15 a.m.-5:25 p.m.

2 stops8h 10m

C$ 611

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Sat 25/4

8:45 a.m.-9:07 p.m.

1 stop14h 22m

San Jose

Tue 28/4

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

2 stops18h 07m

C$ 614

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Mon 1/6

12:00 p.m.-7:19 p.m.

2 stops9h 19m

San Jose

Thu 4/6

11:41 a.m.-12:55 a.m.

2 stops11h 14m

C$ 614

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 12/5

11:55 a.m.-8:38 p.m.

1 stop10h 43m

San Jose

Tue 19/5

8:50 p.m.-10:54 a.m.

2 stops12h 04m

C$ 650

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 5/5

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

1 stop6h 45m

San Jose

Wed 6/5

2:33 p.m.-11:52 a.m.

2 stops19h 19m

C$ 788
Cheapest one-way

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Sat 16/5

6:00 a.m.-5:02 p.m.

2 stops13h 02m

C$ 343

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Sat 16/5

11:55 a.m.-8:38 p.m.

1 stop10h 43m

C$ 345

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Thu 16/4

12:55 p.m.-10:01 p.m.

2 stops11h 06m

C$ 472
Quickest one-way

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Thu 16/4

8:45 a.m.-2:25 p.m.

1 stop7h 40m

C$ 486

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/4

Showing 1-10 of 11 resultsSorted by cheapest first
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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$ 168). Flying from Winnipeg to San Jose, California in February is currently the most expensive (average of C$ 445). 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?

    WestJet and United Airlines can get you from Winnipeg to San Jose, California in just under 14h 22m. Your travel time can differ by up to 13h 51m. 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$ 168). Flying from Winnipeg to San Jose, California in February is currently the most expensive (average of C$ 445). 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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