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Cheap flights from San Jose, CA to Winnipeg from C$ 254

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 23/3. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — YWG
10 Apr — 17 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap 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 11 March 2026.

Fri 1/56:32 p.m.
SJC
-
YWG
2 stops14h 24m
Delta
Mon 4/511:55 a.m.
YWG
-
SJC
1 stop10h 42m
Delta
Deal found 8/3C$ 559
Tue 21/48:45 a.m.
SJC
-
YWG
1 stop10h 12m
United Airlines
Wed 22/42:00 p.m.
YWG
-
SJC
1 stop10h 41m
United Airlines
Deal found 8/3C$ 582
Tue 28/711:30 a.m.
SJC
-
YWG
2 stops11h 25m
WestJet
Tue 4/87:00 a.m.
YWG
-
SJC
2 stops10h 50m
WestJet
Deal found 7/3C$ 597
Mon 14/129:05 a.m.
SJC
-
YWG
2 stops11h 35m
WestJet
Wed 6/112:55 p.m.
YWG
-
SJC
2 stops27h 57m
WestJet
Deal found 10/3C$ 599
Mon 14/129:05 a.m.
SJC
-
YWG
2 stops11h 35m
WestJet
Tue 5/16:15 a.m.
YWG
-
SJC
2 stops10h 37m
WestJet
Deal found 10/3C$ 634
Tue 28/711:30 a.m.
SJC
-
YWG
2 stops11h 25m
WestJet
Wed 5/812:00 p.m.
YWG
-
SJC
2 stops9h 30m
WestJet
Deal found 8/3C$ 682

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 11 March 2026.

Round-trip from

C$ 559

One-way from

C$ 254
Delta
  • Delta
  • 1/5-4/5
  • 3 total stops
  • 25h 06m total
  • San Jose to Winnipeg
Search Deals
United Airlines
  • United Airlines
  • 23/3
  • 1 total stop
  • 11h 02m 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 11 March 2026.
Use the filters below to find and compare flights from San Jose to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Fri 1/5

6:32 p.m.-10:56 a.m.

2 stops14h 24m

Winnipeg

Mon 4/5

11:55 a.m.-8:37 p.m.

1 stop10h 42m

C$ 559

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 21/4

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

1 stop10h 12m

Winnipeg

Wed 22/4

2:00 p.m.-10:41 p.m.

1 stop10h 41m

C$ 582

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 27/5

9:53 a.m.-10:10 p.m.

2 stops10h 17m

Winnipeg

Mon 1/6

10:10 a.m.-7:19 p.m.

2 stops11h 09m

C$ 695

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Fri 24/4

3:45 p.m.-11:52 a.m.

2 stops18h 07m

Winnipeg

Fri 1/5

2:00 p.m.-10:56 p.m.

1 stop10h 56m

C$ 697
Quickest round-trip

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 27/5

6:15 a.m.-3:20 p.m.

1 stop7h 05m

Winnipeg

Mon 1/6

5:41 p.m.-11:41 p.m.

2 stops8h 00m

C$ 705

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Thu 30/7

5:45 a.m.-11:27 p.m.

2 stops15h 42m

Winnipeg

Wed 12/8

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

1 stop10h 13m

C$ 718

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sat 15/8

9:05 a.m.-11:27 p.m.

2 stops12h 22m

Winnipeg

Mon 24/8

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

1 stop10h 13m

C$ 718

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sun 2/8

10:56 p.m.-3:23 p.m.

2 stops14h 27m

Winnipeg

Tue 11/8

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

1 stop10h 13m

C$ 718
Cheapest one-way

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Mon 23/3

10:55 p.m.-11:57 a.m.

1 stop11h 02m

C$ 254
Quickest one-way

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 28/7

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

2 stops8h 10m

C$ 303

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 15 resultsSorted by cheapest first
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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, June is the cheapest month in which you can book a flight from San Jose, California to Winnipeg (average of C$ 155). Flying from San Jose, California to Winnipeg in December is currently the most expensive (average of C$ 524). 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 10h 12m. Delta provides one of the quickest options available for as low as C$ 582. 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, June is the cheapest month in which you can book a flight from San Jose, California to Winnipeg (average of C$ 155). Flying from San Jose, California to Winnipeg in December is currently the most expensive (average of C$ 524). 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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How does Cheapflights help users find flights from San Jose to Winnipeg?

Cheapflights makes it easy to find San Jose to Winnipeg flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from San Jose to Winnipeg?

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Can Cheapflights find flights from San Jose to Winnipeg with no change fees?

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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