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Cheap flights from San Jose, CA to Winnipeg from C$ 264

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 14/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — YWG
28 Nov — 5 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap 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 29 October 2025.

Round-trip from

C$ 616

One-way from

C$ 264
Delta
  • Delta
  • 18/11-21/11
  • 3 total stops
  • 22h 50m total
  • San Jose to Winnipeg
Search Deals
Delta
  • Delta
  • 14/12
  • 1 total stop
  • 8h 35m total
  • San Jose to Winnipeg
Search Deals

Find flight deals from San Jose to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from San Jose to Winnipeg
Explore the most affordable flight options available from San Jose to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 29 October 2025.

Tue 18/118:55 p.m.SJC - YWG
2 stops12h 53mDelta
Fri 21/1112:38 p.m.YWG - SJC
1 stop9h 57mDelta
Deal found 28/10C$ 616
Wed 19/119:40 a.m.SJC - YWG
2 stops11h 56mDelta
Sat 22/1112:38 p.m.YWG - SJC
1 stop9h 57mDelta
Deal found 26/10C$ 667
Sun 23/117:00 a.m.SJC - YWG
2 stops14h 36mDelta
Wed 26/1112:38 p.m.YWG - SJC
1 stop9h 57mDelta
Deal found 28/10C$ 727
Tue 25/116:15 a.m.SJC - YWG
1 stop8h 44mDelta
Fri 28/113:18 p.m.YWG - SJC
1 stop7h 17mDelta
Deal found 28/10C$ 763
Wed 19/118:45 a.m.SJC - YWG
1 stop10h 11mUnited Airlines
Sat 22/118:40 a.m.YWG - SJC
1 stop7h 02mUnited Airlines
Deal found 28/10C$ 805
Tue 2/128:45 a.m.SJC - YWG
1 stop10h 10mUnited Airlines
Fri 5/128:40 a.m.YWG - SJC
1 stop14h 47mUnited Airlines
Deal found 28/10C$ 841
Thu 20/117:05 a.m.SJC - YWG
2 stops13h 36mDelta
Sat 22/117:50 a.m.YWG - SJC
2 stops15h 47mDelta
Deal found 28/10C$ 847
Wed 19/1111:40 a.m.SJC - YWG
2 stops24h 12mWestJet
Sat 22/1112:55 p.m.YWG - SJC
3 stops32h 11mWestJet
Deal found 26/10C$ 848

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 29 October 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

Mon 1/12

6:59 p.m.-11:45 a.m.

2 stops14h 46m

Winnipeg

Thu 4/12

12:35 p.m.-8:36 p.m.

1 stop10h 01m

C$ 616

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 2/12

4:00 p.m.-11:57 a.m.

2 stops17h 57m

Winnipeg

Fri 5/12

8:40 a.m.-5:51 p.m.

1 stop11h 11m

C$ 616

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 18/11

7:46 p.m.-11:48 a.m.

2 stops14h 02m

Winnipeg

Fri 21/11

12:38 p.m.-8:35 p.m.

1 stop9h 57m

C$ 616

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 2/12

7:45 p.m.-11:45 a.m.

2 stops14h 00m

Winnipeg

Fri 5/12

6:40 a.m.-6:57 p.m.

2 stops14h 17m

C$ 625

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 19/11

9:40 a.m.-11:36 p.m.

2 stops11h 56m

Winnipeg

Sat 22/11

12:38 p.m.-8:35 p.m.

1 stop9h 57m

C$ 667

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 25/11

7:00 a.m.-11:36 p.m.

2 stops14h 36m

Winnipeg

Fri 28/11

3:18 p.m.-8:35 p.m.

1 stop7h 17m

C$ 727

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sun 23/11

7:00 a.m.-11:36 p.m.

2 stops14h 36m

Winnipeg

Wed 26/11

12:38 p.m.-8:35 p.m.

1 stop9h 57m

C$ 727

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 15/4

7:15 a.m.-10:40 p.m.

2 stops13h 25m

Winnipeg

Sun 19/4

12:40 p.m.-8:53 p.m.

1 stop10h 13m

C$ 780

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sun 14/12

6:20 a.m.-4:55 p.m.

1 stop8h 35m

C$ 264

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/10

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, February is the cheapest month in which you can book a flight from San Jose, California to Winnipeg (average of C$ 159). Flying from San Jose, California to Winnipeg in November is currently the most expensive (average of C$ 386). 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 46m. Delta provides one of the quickest options available for as low as C$ 616. 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, February is the cheapest month in which you can book a flight from San Jose, California to Winnipeg (average of C$ 159). Flying from San Jose, California to Winnipeg in November is currently the most expensive (average of C$ 386). 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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