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$328+ Cheap flights from San Jose, CA (SJC) to Winnipeg (YWG)

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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — YWG
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
1 adult, Economy
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Cheap flight deals from San Jose to Winnipeg

Best flights from San Jose to Winnipeg
Discover carefully curated flight deals from San Jose to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 8, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/8. 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 1/224:06 pmSJC - YWG
2 stops30h 47mMultiple Airlines
Thu 1/297:30 amYWG - SJC
1 stop9h 41mMultiple Airlines
Deal found 12/8$328
This Delta deal was found by Cheapflights users on 12/8. 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.
Thu 1/225:05 pmSJC - YWG
2 stops15h 58mDelta
Thu 1/296:40 amYWG - SJC
2 stops13h 00mDelta
Deal found 12/8$453
This eDestinos deal was found by Cheapflights users on 12/7. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/243:40 pmSJC - YWG
2 stops24h 25mWestJet
Tue 3/34:10 pmYWG - SJC
2 stops24h 46mWestJet
Deal found 12/7$455
This Delta deal was found by Cheapflights users on 12/7. 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 2/248:59 pmSJC - YWG
2 stops12h 02mDelta
Tue 3/311:53 amYWG - SJC
1 stop11h 00mDelta
Deal found 12/7$509
This Delta deal was found by Cheapflights users on 12/7. 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 1/215:05 pmSJC - YWG
2 stops15h 58mDelta
Wed 1/286:40 amYWG - SJC
2 stops13h 00mDelta
Deal found 12/7$514
This WestJet deal was found by Cheapflights users on 12/6. 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.
Thu 1/1511:40 amSJC - YWG
2 stops34h 59mWestJet
Sun 1/184:10 pmYWG - SJC
2 stops24h 42mWestJet
Deal found 12/6$725
This Mytrip deal was found by Cheapflights users on 12/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2411:30 amSJC - YWG
3 stops22h 02mMultiple Airlines
Tue 3/39:00 pmYWG - SJC
3 stops20h 43mMultiple Airlines
Deal found 12/7$933

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 December 8, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$328
(Kiwi.com)
Provider with most accurate pricing for San Jose-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Jose-Winnipeg flights.
Search Deals
From San Jose to Winnipeg
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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 2,558,603 searches. Data last updated December 8, 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

Thu 1/22

4:06 pm-12:53 am

2 stops30h 47m

Winnipeg

Thu 1/29

7:30 am-3:11 pm

1 stop9h 41m

$328

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Thu 1/22

5:05 pm-11:03 am

2 stops15h 58m

Winnipeg

Thu 1/29

6:40 am-5:40 pm

2 stops13h 00m

$453

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 2/24

3:40 pm-6:05 pm

2 stops24h 25m

Winnipeg

Tue 3/3

4:10 pm-2:56 pm

2 stops24h 46m

$455

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 2/24

8:59 pm-11:01 am

2 stops12h 02m

Winnipeg

Tue 3/3

11:53 am-8:53 pm

1 stop11h 00m

$509

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 1/21

5:05 pm-11:03 am

2 stops15h 58m

Winnipeg

Wed 1/28

6:40 am-5:40 pm

2 stops13h 00m

$514

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Thu 1/15

11:40 am-12:39 am

2 stops34h 59m

Winnipeg

Sun 1/18

4:10 pm-2:52 pm

2 stops24h 42m

$725

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 2/24

11:30 am-11:32 am

3 stops22h 02m

Winnipeg

Tue 3/3

9:00 pm-3:43 pm

3 stops20h 43m

$933

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/8

  • Most accurate provider: When it comes to deals on San Jose, California-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Jose, California-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Jose, California-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Jose, California-Winnipeg 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 San Jose, California-Winnipeg 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 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, March is the cheapest month in which you can book a flight from San Jose, California to Winnipeg (average of $111). Flying from San Jose, California to Winnipeg in December is currently the most expensive (average of $310). 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?

    For as low as $453, Delta can have you in Winnipeg from San Jose, California in 15h 58m. There are 1496 mi between San Jose, California and Winnipeg. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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, March is the cheapest month in which you can book a flight from San Jose, California to Winnipeg (average of $111). Flying from San Jose, California to Winnipeg in December is currently the most expensive (average of $310). 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

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

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