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Cheap flights from San Jose to Winnipeg from C$ 522

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 23/9. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — YWG
11 Oct — 18 Oct1
1 adult
1 adult, Economy

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 11 September 2025.

Round-trip from

C$ 522
23/9-26/9
  • 23/9-26/9
  • 6 total stops
  • 62h 33m total
  • San Jose to Winnipeg
Search Deals

Find flight deals from San Jose to Winnipeg

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 September 2025.

Tue 23/96:35 a.m.SJC - YWG
3 stops34h 48mMultiple Airlines
Fri 26/99:00 a.m.YWG - SJC
3 stops27h 45mMultiple Airlines
Deal found 9/9C$ 522
Tue 23/97:00 a.m.SJC - YWG
2 stops14h 27mDelta
Fri 26/98:35 a.m.YWG - SJC
2 stops11h 39mDelta
Deal found 9/9C$ 739
Mon 15/96:35 a.m.SJC - YWG
3 stops36h 50mMultiple Airlines
Mon 22/93:15 p.m.YWG - SJC
3 stops30h 45mMultiple Airlines
Deal found 11/9C$ 880
Mon 15/911:40 a.m.SJC - YWG
3 stops34h 00mMultiple Airlines
Tue 23/93:15 p.m.YWG - SJC
3 stops30h 45mMultiple Airlines
Deal found 11/9C$ 881
Sat 25/106:30 a.m.SJC - YWG
1 stop14h 03mUnited Airlines
Sat 1/118:40 a.m.YWG - SJC
1 stop7h 02mUnited Airlines
Deal found 10/9C$ 1,070
Sat 25/103:22 p.m.SJC - YWG
2 stops30h 28mWestJet
Sat 1/117:50 a.m.YWG - SJC
2 stops12h 58mWestJet
Deal found 10/9C$ 1,236

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 September 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

Tue 23/9

6:35 a.m.-7:23 p.m.

3 stops34h 48m

Winnipeg

Fri 26/9

9:00 a.m.-10:45 a.m.

3 stops27h 45m

C$ 522

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 23/9

7:00 a.m.-11:27 p.m.

2 stops14h 27m

Winnipeg

Fri 26/9

8:35 a.m.-6:14 p.m.

2 stops11h 39m

C$ 739

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 10/3

6:30 a.m.-5:00 p.m.

1 stop8h 30m

Winnipeg

Wed 11/3

5:38 p.m.-8:20 a.m.

2 stops16h 42m

C$ 909

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sat 25/10

6:30 a.m.-10:33 p.m.

1 stop14h 03m

Winnipeg

Sat 1/11

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

1 stop7h 02m

C$ 1,070

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 10/3

3:35 p.m.-11:39 a.m.

2 stops18h 04m

Winnipeg

Wed 11/3

9:40 p.m.-5:43 p.m.

2 stops22h 03m

C$ 1,183

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sat 25/10

3:22 p.m.-11:50 p.m.

2 stops30h 28m

Winnipeg

Sat 1/11

7:50 a.m.-6:48 p.m.

2 stops12h 58m

C$ 1,236

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 23/9

9:02 a.m.-8:15 p.m.

2 stops9h 13m

C$ 636

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 23/9

6:30 a.m.-10:33 p.m.

1 stop14h 03m

C$ 636

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 16/9

7:14 a.m.-11:10 p.m.

2 stops13h 56m

C$ 766

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 17/9

8:45 a.m.-11:08 a.m.

2 stops24h 23m

C$ 843

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

Showing 1-10 of 13 results
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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 to Winnipeg?

Currently, January is the cheapest month in which you can book a flight from San Jose to Winnipeg (average of C$ 123). Flying from San Jose to Winnipeg in July is currently the most expensive (average of C$ 232). 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 to Winnipeg?

    A quick flight from San Jose to Winnipeg can take about 14h 27m. Delta provides one of the quickest options available for as low as C$ 739. There are 2408 km between San Jose and Winnipeg.

  • What are the cheapest airlines to fly from San Jose to Winnipeg one-way?

    The cheapest airlines for a one-way flight from San Jose to Winnipeg are WestJet (C$ 636), United Airlines (C$ 636), and Air Canada (C$ 843).

  • 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 to Winnipeg?

    Currently, January is the cheapest month in which you can book a flight from San Jose to Winnipeg (average of C$ 123). Flying from San Jose to Winnipeg in July is currently the most expensive (average of C$ 232). 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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