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Cheap flights from Winnipeg to San Jose from C$ 249

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 30/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJC
16 Oct — 23 Oct1
1 adult
1 adult, Economy

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 16 September 2025.

Round-trip from

C$ 705

One-way from

C$ 249
Delta
  • Delta
  • 10/10-14/10
  • 3 total stops
  • 24h 01m total
  • Winnipeg to San Jose
Search Deals
30/10
  • 30/10
  • 2 total stops
  • 34h 29m 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 16 September 2025.

Fri 10/1012:20 p.m.YWG - SJC
1 stop10h 06mDelta
Tue 14/107:35 p.m.SJC - YWG
2 stops13h 55mDelta
Deal found 16/9C$ 705
Fri 10/108:15 p.m.YWG - SJC
2 stops20h 27mWestJet
Tue 14/107:15 a.m.SJC - YWG
3 stops32h 10mWestJet
Deal found 16/9C$ 752

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 16 September 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

Fri 10/10

12:20 p.m.-8:26 p.m.

1 stop10h 06m

San Jose

Tue 14/10

7:35 p.m.-11:30 a.m.

2 stops13h 55m

C$ 705

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Fri 10/10

8:15 p.m.-2:42 p.m.

2 stops20h 27m

San Jose

Tue 14/10

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

3 stops32h 10m

C$ 752

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Thu 30/10

9:05 a.m.-5:34 p.m.

2 stops34h 29m

C$ 249

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Fri 31/10

12:40 p.m.-10:09 a.m.

3 stops23h 29m

C$ 297

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Thu 30/10

8:40 a.m.-1:42 p.m.

1 stop7h 02m

C$ 446

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Fri 31/10

2:20 p.m.-10:30 p.m.

1 stop10h 10m

C$ 453

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/9

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.

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?

    Departing from Winnipeg to San Jose will take you 10h 06m. Winnipeg and San Jose are separated by a distance of 2408 km. 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?

    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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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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