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Cheap flights from San Jose, CA to Winnipeg from C$ 741

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 24/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — YWG
11 Jan — 18 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from San Jose to Winnipeg

Enter your travel dates to find the best prices.

Best flights from San Jose to Winnipeg
Discover carefully curated flight deals from San Jose to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 12 December 2025.

Sat 24/18:40 a.m.SJC - YWG
2 stops26h 19mAir Canada
Sat 31/110:45 a.m.YWG - SJC
2 stops12h 11mAir Canada
Deal found 10/12C$ 741
Mon 26/17:45 a.m.SJC - YWG
2 stops14h 56mWestJet
Mon 2/24:10 p.m.YWG - SJC
2 stops24h 43mWestJet
Deal found 11/12C$ 743
Mon 26/18:05 p.m.SJC - YWG
2 stops12h 58mDelta
Mon 2/211:53 a.m.YWG - SJC
1 stop11h 35mDelta
Deal found 11/12C$ 1,110
Sat 24/111:51 a.m.SJC - YWG
3 stops33h 44mAmerican Airlines
Sat 31/16:00 a.m.YWG - SJC
3 stops17h 29mAmerican Airlines
Deal found 10/12C$ 1,433
Thu 15/111:40 a.m.SJC - YWG
2 stops34h 59mWestJet
Sun 18/14:10 p.m.YWG - SJC
2 stops29h 02mWestJet
Deal found 11/12C$ 912

Find flight deals from San Jose to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) to Winnipeg (YWG). 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 12 December 2025.

Round-trip from

C$ 741
Air Canada
  • Air Canada
  • 24/1-31/1
  • 4 total stops
  • 38h 30m total
  • San Jose to Winnipeg
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Jose to Winnipeg 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 12 December 2025.
Use the filters below to find and compare flights from San Jose to Winnipeg that are best for you.

Fly from

San Jose

Fly to

Winnipeg

Route

Depart

Return

Price

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sat 24/1

8:40 a.m.-12:59 p.m.

2 stops26h 19m

Winnipeg

Sat 31/1

10:45 a.m.-8:56 p.m.

2 stops12h 11m

C$ 741

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Mon 26/1

7:45 a.m.-12:41 a.m.

2 stops14h 56m

Winnipeg

Mon 2/2

4:10 p.m.-2:53 p.m.

2 stops24h 43m

C$ 743

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Thu 15/1

11:40 a.m.-12:39 a.m.

2 stops34h 59m

Winnipeg

Sun 18/1

4:10 p.m.-7:12 p.m.

2 stops29h 02m

C$ 912

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Mon 26/1

8:05 p.m.-11:03 a.m.

2 stops12h 58m

Winnipeg

Mon 2/2

11:53 a.m.-9:28 p.m.

1 stop11h 35m

C$ 1,110

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sat 24/1

11:51 a.m.-11:35 p.m.

3 stops33h 44m

Winnipeg

Sat 31/1

6:00 a.m.-9:29 p.m.

3 stops17h 29m

C$ 1,433

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Best time to book a flight from San Jose to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from San Jose 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 San Jose to Winnipeg

What is the cheapest month to book a flight from San Jose, California to Winnipeg?

Currently, March is the cheapest month in which you can book a flight from San Jose, California to Winnipeg (average of C$ 153). Flying from San Jose, California to Winnipeg in December is currently the most expensive (average of C$ 428). 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 San Jose to Winnipeg. 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 San Jose, California to Winnipeg?

    A quick flight from San Jose, California to Winnipeg can take about 14h 56m. Air Canada provides one of the quickest options available for as low as C$ 743. San Jose, California and Winnipeg are separated by a distance of 2408 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • Can I find deals for flights from San Jose to Winnipeg that include hotel bookings?

    Yes. In addition to deals on San Jose to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Jose to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Jose to Winnipeg.

  • Can I find deals for business class flights from San Jose to Winnipeg?

    Yes. Cheapflights offers flight deals from San Jose to Winnipeg 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 San Jose, California to Winnipeg?

    Currently, March is the cheapest month in which you can book a flight from San Jose, California to Winnipeg (average of C$ 153). Flying from San Jose, California to Winnipeg in December is currently the most expensive (average of C$ 428). 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

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Selkirk
Portage la Prairie

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Yes! Cheapflights helps users easily find flights from San Jose to Winnipeg with no change fees.

Can Cheapflights notify me if prices for flights from San Jose to Winnipeg become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Winnipeg from San Jose today and book when prices fit your budget.

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