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Cheap flights from Winnipeg to San Jose from C$ 247

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 15/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJC
19 Aug — 26 Aug1
1 adult

Cheap 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 August 2025.

Round-trip from

C$ 574

One-way from

C$ 247
Delta
  • Delta
  • 7/1-4/2
  • 4 total stops
  • 37h 19m total
  • Winnipeg to San Jose
Search Deals
15/12
  • 15/12
  • 3 total stops
  • 26h 59m total
  • Winnipeg to San Jose
Search Deals

Find 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 14 August 2025.

Sat 30/88:35 a.m.YWG - SJC
2 stops12h 38mDelta
Wed 3/910:56 p.m.SJC - YWG
2 stops10h 55mDelta
Deal found 14/8C$ 753
Thu 28/88:35 a.m.YWG - SJC
2 stops17h 04mDelta
Mon 1/91:44 p.m.SJC - YWG
2 stops20h 07mDelta
Deal found 14/8C$ 800
Thu 28/812:43 p.m.YWG - SJC
2 stops12h 06mDelta
Wed 3/97:23 a.m.SJC - YWG
2 stops12h 07mDelta
Deal found 14/8C$ 871
Fri 29/86:40 a.m.YWG - SJC
2 stops12h 24mDelta
Mon 1/93:17 p.m.SJC - YWG
2 stops18h 34mDelta
Deal found 14/8C$ 885
Fri 29/82:20 p.m.YWG - SJC
1 stop10h 20mUnited Airlines
Tue 2/96:30 a.m.SJC - YWG
1 stop14h 03mUnited Airlines
Deal found 14/8C$ 1,030
Thu 28/86:30 a.m.YWG - SJC
2 stops11h 37mWestJet
Tue 2/97:23 a.m.SJC - YWG
2 stops13h 47mWestJet
Deal found 14/8C$ 1,161
Thu 28/84:25 p.m.YWG - SJC
1 stop6h 53mAir Canada
Tue 2/98:45 a.m.SJC - YWG
2 stops14h 57mAir Canada
Deal found 14/8C$ 1,172
Sat 30/810:25 a.m.YWG - SJC
2 stops12h 42mAir Canada
Tue 2/98:45 a.m.SJC - YWG
2 stops14h 57mAir Canada
Deal found 14/8C$ 1,179

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 August 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

Wed 7/1

6:40 a.m.-10:06 p.m.

2 stops17h 26m

San Jose

Wed 4/2

1:50 p.m.-11:43 a.m.

2 stops19h 53m

C$ 574

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 6/1

12:40 p.m.-10:50 a.m.

2 stops24h 10m

San Jose

Wed 4/2

3:45 p.m.-11:43 a.m.

2 stops17h 58m

C$ 574

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Mon 12/1

12:40 p.m.-10:50 a.m.

2 stops24h 10m

San Jose

Wed 4/2

9:05 a.m.-11:43 a.m.

2 stops24h 38m

C$ 574

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Wed 7/1

6:40 a.m.-10:06 p.m.

2 stops17h 26m

San Jose

Sat 7/2

7:10 a.m.-11:33 p.m.

2 stops14h 23m

C$ 575

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 6/1

12:40 p.m.-10:50 a.m.

2 stops24h 10m

San Jose

Sat 7/2

7:10 a.m.-11:33 p.m.

2 stops14h 23m

C$ 575

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Mon 12/1

12:40 p.m.-10:50 a.m.

2 stops24h 10m

San Jose

Sat 7/2

7:10 a.m.-11:33 p.m.

2 stops14h 23m

C$ 575

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Mon 12/1

8:00 a.m.-9:32 a.m.

1 stop27h 32m

San Jose

Wed 4/2

6:45 p.m.-6:05 p.m.

2 stops21h 20m

C$ 586

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Mon 12/1

8:00 a.m.-9:32 a.m.

1 stop27h 32m

San Jose

Tue 10/2

6:45 p.m.-6:05 p.m.

2 stops21h 20m

C$ 586

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Thu 8/1

12:40 p.m.-10:50 a.m.

2 stops24h 10m

San Jose

Wed 4/2

3:45 p.m.-11:43 a.m.

2 stops17h 58m

C$ 602

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Sun 11/1

6:40 a.m.-10:06 p.m.

2 stops17h 26m

San Jose

Wed 4/2

3:45 p.m.-11:43 a.m.

2 stops17h 58m

C$ 602

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/8

Showing 1-10 of 13 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?

Currently, September is the cheapest month in which you can book a flight from Winnipeg to San Jose (average of C$ 331). Flying from Winnipeg to San Jose in December is currently the most expensive (average of C$ 459). 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.

What’s the top layover airport for flights from Winnipeg to San Jose?

Share of one-stop round-trip flights from Winnipeg to San Jose chosen by Cheapflights users in the past 12 months, using the same layover each way.

Los Angeles (LAX) – chosen by Cheapflights users on 50% of one-stop itineraries from Winnipeg to San Jose on Cheapflights.

What’s the cheapest layover airport for flights from Winnipeg to San Jose?

Average round-trip fare for 1-stop flights from Winnipeg to San Jose, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of C$ 849.

What’s the fastest layover option from Winnipeg to San Jose?

Shortest average travel time for 1-stop one-way flights from Winnipeg to San Jose, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 6h 13m.

Which airport typically offers the quickest layover for flights from Winnipeg to San Jose?

Average layover duration for 1-stop one-way flights from Winnipeg to San Jose, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Los Angeles (LAX) offer the fastest connection on this route, with an average layover time of 1h 44m.

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.

  • 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?

    Currently, September is the cheapest month in which you can book a flight from Winnipeg to San Jose (average of C$ 331). Flying from Winnipeg to San Jose in December is currently the most expensive (average of C$ 459). 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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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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