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$396+ Cheap flights from San Jose, CA (SJC) to Winnipeg (YWG)

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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — YWG
Dec 24 — Dec 311
Wed 12/24
Wed 12/31
1 adult, Economy
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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 November 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$491
(Priceline)

One-way from

$396
(United Airlines)
Provider with most accurate pricing for San Jose-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for San Jose-Winnipeg flights.
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From San Jose to Winnipeg
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One-way flight from San Jose to Winnipeg
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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 November 24, 2025.

This Delta deal was found by Cheapflights users on 11/22. 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.
Fri 12/266:20 amSJC - YWG
1 stop8h 35mDelta
Sun 1/1111:53 amYWG - SJC
1 stop11h 35mDelta
Deal found 11/22$553
This Delta deal was found by Cheapflights users on 11/21. 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.
Mon 12/87:15 amSJC - YWG
2 stops26h 30mDelta
Thu 12/1112:35 pmYWG - SJC
2 stops26h 21mDelta
Deal found 11/21$576
This Delta deal was found by Cheapflights users on 11/22. 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 12/277:45 pmSJC - YWG
2 stops14h 00mDelta
Sun 1/1111:53 amYWG - SJC
2 stops13h 02mDelta
Deal found 11/22$635
This Kiwi.com deal was found by Cheapflights users on 11/22. 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.
Fri 12/267:13 amSJC - YWG
2 stops15h 28mMultiple Airlines
Mon 1/128:00 amYWG - SJC
1 stop12h 14mMultiple Airlines
Deal found 11/22$666
This Delta deal was found by Cheapflights users on 11/22. 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.
Fri 12/267:45 pmSJC - YWG
2 stops14h 00mDelta
Mon 1/126:40 amYWG - SJC
2 stops14h 32mDelta
Deal found 11/22$691
This United Airlines deal was found by Cheapflights users on 11/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/88:45 amSJC - YWG
1 stop10h 10mUnited Airlines
Thu 12/118:40 amYWG - SJC
1 stop14h 47mUnited Airlines
Deal found 11/22$719
This Mytrip deal was found by Cheapflights users on 11/22. 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.
Fri 12/265:40 pmSJC - YWG
2 stops29h 01mWestJet
Mon 1/129:00 pmYWG - SJC
3 stops19h 52mWestJet
Deal found 11/22$780

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 November 24, 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

Sun 2/15

9:17 am-10:40 pm

2 stops11h 23m

Winnipeg

Wed 2/18

6:15 am-2:56 pm

2 stops10h 41m

$491

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 1/7

9:55 am-12:43 am

1 stop12h 48m

Winnipeg

Wed 1/14

4:10 pm-6:37 pm

2 stops28h 27m

$495

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 1/7

9:15 am-12:39 am

2 stops13h 24m

Winnipeg

Wed 1/14

9:00 pm-2:52 pm

3 stops19h 52m

$505

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 1/7

6:20 am-4:29 pm

1 stop8h 09m

Winnipeg

Wed 1/14

11:53 am-9:28 pm

1 stop11h 35m

$553

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Fri 12/26

6:20 am-4:55 pm

1 stop8h 35m

Winnipeg

Sun 1/11

11:53 am-9:28 pm

1 stop11h 35m

$553

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sat 12/27

6:20 am-4:55 pm

1 stop8h 35m

Winnipeg

Sun 1/11

11:53 am-9:28 pm

1 stop11h 35m

$553

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Mon 12/8

7:15 am-11:45 am

2 stops26h 30m

Winnipeg

Thu 12/11

12:35 pm-12:56 pm

2 stops26h 21m

$576

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sun 2/15

11:37 am-3:42 pm

1 stop26h 05m

Winnipeg

Wed 2/18

6:45 am-5:09 pm

2 stops12h 24m

$638

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Mon 12/15

8:45 am-8:55 pm

1 stop10h 10m

$396

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Mon 12/15

9:04 am-6:06 pm

2 stops31h 02m

$472

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

  • 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 November is currently the most expensive (average of $290). 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 $553, WestJet can have you in Winnipeg from San Jose, California in 8h 09m. 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 November is currently the most expensive (average of $290). 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

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