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Cheap flights from Winnipeg to San Jose, CA from C$ 424

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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJC
31 Jul — 7 Aug1
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 1 July 2026.

Wed 28/106:35 a.m.
YWG
-
SJC
2 stops9h 34m
Delta
Sat 31/105:45 p.m.
SJC
-
YWG
2 stops17h 05m
Delta
Deal found 25/6C$ 636
Sat 19/97:00 a.m.
YWG
-
SJC
2 stops15h 08m
Multiple Airlines
Mon 21/92:24 p.m.
SJC
-
YWG
1 stop8h 11m
Multiple Airlines
Deal found 28/6C$ 651
Wed 26/812:46 p.m.
YWG
-
SJC
2 stops9h 27m
Delta
Sun 30/86:10 a.m.
SJC
-
YWG
1 stop6h 58m
Delta
Deal found 28/6C$ 728
Sat 19/93:58 p.m.
YWG
-
SJC
2 stops8h 10m
Delta
Mon 21/98:53 p.m.
SJC
-
YWG
2 stops13h 03m
Delta
Deal found 28/6C$ 739
Wed 28/108:30 a.m.
YWG
-
SJC
1 stop6h 36m
United Airlines
Sat 31/104:10 p.m.
SJC
-
YWG
2 stops18h 29m
United Airlines
Deal found 25/6C$ 775
Thu 10/92:55 p.m.
YWG
-
SJC
2 stops9h 50m
WestJet
Thu 17/97:25 a.m.
SJC
-
YWG
2 stops8h 00m
WestJet
Deal found 26/6C$ 810
Wed 28/106:15 a.m.
YWG
-
SJC
2 stops9h 58m
WestJet
Sun 1/117:00 a.m.
SJC
-
YWG
2 stops12h 40m
WestJet
Deal found 28/6C$ 829

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 1 July 2026.

Round-trip from

C$ 638

One-way from

C$ 424
Delta
  • Delta
  • 28/10-31/10
  • 4 total stops
  • 26h 39m total
  • Winnipeg to San Jose
Search Deals
10/8
  • 10/8
  • 3 total stops
  • 27h 05m 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 1 July 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

Wed 28/10

6:35 a.m.-2:09 p.m.

2 stops9h 34m

San Jose

Sat 31/10

5:45 p.m.-12:50 p.m.

2 stops17h 05m

C$ 636

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Wed 28/10

8:30 a.m.-1:06 p.m.

1 stop6h 36m

San Jose

Sat 31/10

4:10 p.m.-12:39 p.m.

2 stops18h 29m

C$ 775
Quickest round-trip

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Wed 26/8

3:58 p.m.-8:24 p.m.

1 stop6h 26m

San Jose

Sun 30/8

6:10 a.m.-3:08 p.m.

1 stop6h 58m

C$ 776

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Wed 26/8

7:00 a.m.-8:57 p.m.

2 stops15h 57m

San Jose

Sun 30/8

8:45 a.m.-11:52 a.m.

2 stops25h 07m

C$ 776

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Thu 10/9

2:55 p.m.-10:45 p.m.

2 stops9h 50m

San Jose

Thu 17/9

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

2 stops8h 00m

C$ 810

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Sat 19/9

8:45 a.m.-8:57 p.m.

1 stop14h 12m

San Jose

Mon 21/9

8:45 a.m.-8:57 p.m.

1 stop10h 12m

C$ 837
Cheapest one-way
Quickest one-way

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Wed 29/7

6:00 a.m.-2:15 p.m.

2 stops10h 15m

C$ 434

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 28/7

8:45 a.m.-9:09 p.m.

1 stop14h 24m

C$ 468

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 28/7

9:05 p.m.-2:15 p.m.

2 stops19h 10m

C$ 476

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/6

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.

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?

    Delta and United Airlines can get you from Winnipeg to San Jose, California in just under 6h 36m. Your travel time can differ by up to 2h 58m. 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.

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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