HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San Jose

$170+ Cheap flights from Winnipeg (YWG) to San Jose, CA (SJC)

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 3/15. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJC
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Winnipeg to San Jose with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Winnipeg to San Jose

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 January 29, 2026.

This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/75:20 pm
YWG
-
SJC
2 stops8h 38m
Delta
Tue 4/148:05 pm
SJC
-
YWG
2 stops12h 51m
Delta
Deal found 1/26$352
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1211:55 am
YWG
-
SJC
1 stop10h 29m
Delta
Sun 4/199:37 am
SJC
-
YWG
2 stops11h 53m
Delta
Deal found 1/26$373
This Justfly.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:55 pm
YWG
-
SJC
2 stops28h 01m
WestJet
Tue 3/39:15 am
SJC
-
YWG
2 stops30h 50m
WestJet
Deal found 1/28$383
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/811:55 am
YWG
-
SJC
1 stop10h 29m
Delta
Thu 4/166:45 am
SJC
-
YWG
2 stops26h 11m
Delta
Deal found 1/26$384
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1811:55 am
YWG
-
SJC
2 stops11h 26m
Delta
Fri 4/247:20 am
SJC
-
YWG
2 stops14h 10m
Delta
Deal found 1/26$395
This WestJet deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/174:10 pm
YWG
-
SJC
2 stops23h 07m
WestJet
Fri 4/244:10 pm
SJC
-
YWG
2 stops23h 55m
WestJet
Deal found 1/26$398
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2511:55 am
YWG
-
SJC
1 stop10h 29m
Delta
Wed 4/17:15 am
SJC
-
YWG
2 stops14h 20m
Delta
Deal found 1/26$399
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:30 am
YWG
-
SJC
1 stop12h 24m
Multiple Airlines
Tue 3/36:03 pm
SJC
-
YWG
2 stops17h 49m
Multiple Airlines
Deal found 1/28$401
This Delta deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/811:55 am
YWG
-
SJC
1 stop10h 29m
Delta
Thu 3/126:00 am
SJC
-
YWG
2 stops10h 05m
Delta
Deal found 1/27$406
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1811:55 am
YWG
-
SJC
2 stops11h 26m
Delta
Sat 4/256:00 pm
SJC
-
YWG
2 stops14h 56m
Delta
Deal found 1/26$420
This WestJet deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/244:10 pm
YWG
-
SJC
2 stops24h 29m
WestJet
Tue 3/3111:40 am
SJC
-
YWG
2 stops9h 00m
WestJet
Deal found 1/26$422
This WestJet deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/84:10 pm
YWG
-
SJC
2 stops24h 29m
WestJet
Thu 3/129:15 am
SJC
-
YWG
2 stops11h 25m
WestJet
Deal found 1/28$425

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$352
(Delta)

One-way from

$198
(Kiwi.com)
Provider with most accurate pricing for Winnipeg-San Jose flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-San Jose flights.
Search Deals
From Winnipeg to San Jose
Search Deals
One-way flight from 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 2,558,603 searches. Data last updated January 29, 2026.
Use the filters below to find and compare flights from Winnipeg to San Jose that are best for you.

Fly from

Winnipeg

Fly to

San Jose

Route

Depart

Return

Price

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Wed 4/22

8:45 am-1:35 pm

1 stop6h 50m

San Jose

Wed 4/29

3:45 pm-11:52 am

2 stops18h 07m

$352

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Mon 4/6

5:20 pm-11:58 pm

2 stops8h 38m

San Jose

Mon 4/13

8:05 pm-10:56 am

2 stops12h 51m

$352

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 3/10

2:20 pm-10:59 pm

1 stop10h 39m

San Jose

Thu 3/12

10:55 pm-11:57 am

1 stop11h 02m

$352

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Mon 4/13

11:55 am-8:37 pm

1 stop10h 42m

San Jose

Tue 4/21

8:05 pm-10:56 am

2 stops12h 51m

$352

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 3/31

2:00 pm-10:36 pm

1 stop10h 36m

San Jose

Wed 4/8

8:45 am-8:57 pm

1 stop10h 12m

$352

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 4/14

11:55 am-8:37 pm

1 stop10h 42m

San Jose

Wed 4/22

8:05 pm-10:56 am

2 stops12h 51m

$352

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Wed 4/1

2:00 pm-10:36 pm

1 stop10h 36m

San Jose

Tue 4/7

3:45 pm-11:52 am

2 stops18h 07m

$352

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Thu 4/16

11:55 am-11:41 pm

2 stops13h 46m

San Jose

Thu 4/23

8:05 pm-10:56 am

2 stops12h 51m

$352

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Tue 3/31

2:00 pm-10:36 pm

1 stop10h 36m

San Jose

Tue 4/7

3:45 pm-11:52 am

2 stops18h 07m

$352

WinnipegSan Jose

YWG - SJC

YWGSJC

Winnipeg

Wed 4/8

11:55 am-8:24 pm

1 stop10h 29m

San Jose

Tue 4/14

8:05 pm-10:56 am

2 stops12h 51m

$352

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 17 results
1
2
  • Most accurate provider: When it comes to deals on Winnipeg-San Jose, California flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-San Jose, California flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-San Jose, California flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Winnipeg-San Jose, California flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Winnipeg-San Jose, California flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to San Jose

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

Currently, October is the cheapest month in which you can book a flight from Winnipeg to San Jose, California (average of $139). Flying from Winnipeg to San Jose, California in December is currently the most expensive (average of $217). 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 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?

    There are many flights that can get you from Winnipeg to San Jose, California in 6h 50m. Fly via United Airlines or Delta to get the fastest option. The distance between Winnipeg and San Jose, California is about 1496 mi. This flight may include one or multiple stops.

  • 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.

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

    Currently, October is the cheapest month in which you can book a flight from Winnipeg to San Jose, California (average of $139). Flying from Winnipeg to San Jose, California in December is currently the most expensive (average of $217). 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

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.

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.