Find flights
When to book
FAQs

Cheap flights from Winnipeg to San Jose, CA from C$ 398

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 29/7. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJC
26 Jun — 3 Jul1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to San Jose

Enter your travel dates to find the best prices.

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 27 May 2026.

Sun 18/108:00 a.m.
YWG
-
SJC
2 stops12h 20m
Delta
Tue 20/107:35 p.m.
SJC
-
YWG
2 stops14h 15m
Delta
Deal found 24/5C$ 758
Thu 25/610:10 a.m.
YWG
-
SJC
2 stops11h 25m
WestJet
Thu 2/72:59 p.m.
SJC
-
YWG
2 stops29h 11m
WestJet
Deal found 26/5C$ 779
Mon 3/82:55 p.m.
YWG
-
SJC
2 stops33h 18m
WestJet
Fri 7/811:33 a.m.
SJC
-
YWG
2 stops10h 07m
WestJet
Deal found 23/5C$ 802
Sun 22/115:40 a.m.
YWG
-
SJC
2 stops17h 31m
Air Canada
Sun 29/116:30 p.m.
SJC
-
YWG
2 stops21h 39m
Air Canada
Deal found 27/5C$ 1,009
Sun 18/108:30 a.m.
YWG
-
SJC
1 stop14h 34m
United Airlines
Tue 20/106:30 a.m.
SJC
-
YWG
1 stop13h 54m
United Airlines
Deal found 24/5C$ 1,020

Find 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 27 May 2026.

Round-trip from

C$ 779

One-way from

C$ 398
WestJet
  • WestJet
  • 25/6-2/7
  • 4 total stops
  • 40h 36m total
  • Winnipeg to San Jose
Search Deals
Delta
  • Delta
  • 29/7
  • 2 total stops
  • 7h 58m total
  • Winnipeg to San Jose
Search Deals

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 27 May 2026.
Use the filters below to find and compare flights from Winnipeg to San Jose that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Sun 18/10

8:00 a.m.-6:20 p.m.

2 stops12h 20m

San Jose

Tue 20/10

7:35 p.m.-11:50 a.m.

2 stops14h 15m

C$ 758

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Thu 25/6

10:10 a.m.-7:35 p.m.

2 stops11h 25m

San Jose

Thu 2/7

2:59 p.m.-10:10 p.m.

2 stops29h 11m

C$ 779
Quickest round-trip

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Sun 22/11

12:30 p.m.-8:58 p.m.

1 stop10h 28m

San Jose

Sun 29/11

7:35 p.m.-11:50 a.m.

2 stops14h 15m

C$ 816

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Sun 18/10

8:30 a.m.-9:04 p.m.

1 stop14h 34m

San Jose

Tue 20/10

6:30 a.m.-10:24 p.m.

1 stop13h 54m

C$ 1,020
Cheapest one-way
Quickest one-way

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Wed 29/7

5:41 p.m.-11:39 p.m.

2 stops7h 58m

C$ 398

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Wed 29/7

2:55 p.m.-10:48 p.m.

2 stops9h 53m

C$ 399

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 28/7

12:00 p.m.-7:32 p.m.

2 stops9h 32m

C$ 429

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Mon 13/7

7:00 a.m.-3:46 p.m.

2 stops10h 46m

C$ 429

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Wed 15/7

12:00 p.m.-7:32 p.m.

2 stops9h 32m

C$ 429

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/5

Sorted by cheapest first

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.

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, California?

    Delta can get you from Winnipeg to San Jose, California in just under 12h 20m. Your travel time can differ by up to . There are 2408 km between Winnipeg and San Jose, California.

  • 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.