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$181+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — YWG
Mar 24 — Mar 311
Tue 3/24
Tue 3/31
1 adult, Economy
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Cheap 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 February 22, 2026.

This United Airlines deal was found by Cheapflights users on 2/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/88:45 am
SJC
-
YWG
2 stops25h 07m
United Airlines
Wed 4/152:00 pm
YWG
-
SJC
1 stop10h 36m
United Airlines
Deal found 2/21$417
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1611:30 am
SJC
-
YWG
2 stops10h 10m
WestJet
Sat 7/254:55 pm
YWG
-
SJC
2 stops26h 19m
WestJet
Deal found 2/20$440
This Justfly.com deal was found by Cheapflights users on 2/22. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1311:30 am
SJC
-
YWG
2 stops11h 25m
WestJet
Sat 6/207:00 am
YWG
-
SJC
2 stops12h 14m
WestJet
Deal found 2/22$464
This FlightHub deal was found by Cheapflights users on 2/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/121:50 pm
SJC
-
YWG
2 stops25h 35m
WestJet
Tue 10/274:10 pm
YWG
-
SJC
2 stops24h 42m
WestJet
Deal found 2/22$469
This Delta deal was found by Cheapflights users on 2/21. 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.
Tue 8/181:15 pm
SJC
-
YWG
1 stop8h 12m
Delta
Tue 8/256:40 am
YWG
-
SJC
1 stop7h 29m
Delta
Deal found 2/21$497
This Delta deal was found by Cheapflights users on 2/20. 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 3/96:15 pm
SJC
-
YWG
2 stops14h 46m
Delta
Wed 3/1111:55 am
YWG
-
SJC
1 stop10h 29m
Delta
Deal found 2/20$498
This WestJet deal was found by Cheapflights users on 2/21. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/411:41 am
SJC
-
YWG
2 stops11h 14m
WestJet
Mon 6/87:00 am
YWG
-
SJC
2 stops10h 50m
WestJet
Deal found 2/21$502
This Delta deal was found by Cheapflights users on 2/20. 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 3/96:15 pm
SJC
-
YWG
2 stops14h 46m
Delta
Thu 3/1211:55 am
YWG
-
SJC
2 stops14h 03m
Delta
Deal found 2/20$503
This Delta deal was found by Cheapflights users on 2/22. 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.
Mon 10/129:05 am
SJC
-
YWG
2 stops12h 29m
Delta
Tue 10/276:40 am
YWG
-
SJC
1 stop7h 36m
Delta
Deal found 2/22$507
This United Airlines deal was found by Cheapflights users on 2/20. 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 3/910:55 pm
SJC
-
YWG
1 stop11h 02m
United Airlines
Wed 3/112:20 pm
YWG
-
SJC
1 stop10h 39m
United Airlines
Deal found 2/20$515
This WestJet deal was found by Cheapflights users on 2/21. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/83:37 pm
SJC
-
YWG
2 stops44h 15m
WestJet
Wed 4/156:15 am
YWG
-
SJC
2 stops14h 52m
WestJet
Deal found 2/21$521
This Delta deal was found by Cheapflights users on 2/20. 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 3/49:10 pm
SJC
-
YWG
2 stops11h 51m
Delta
Wed 3/1111:55 am
YWG
-
SJC
1 stop10h 29m
Delta
Deal found 2/20$524

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 February 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$417
(United Airlines)

One-way from

$181
(Delta)
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
Search Deals
One-way flight from San Jose to Winnipeg
Search Deals

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 February 22, 2026.
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

Wed 4/8

8:45 am-11:52 am

2 stops25h 07m

Winnipeg

Wed 4/15

2:00 pm-10:36 pm

1 stop10h 36m

$417

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 8/18

9:05 am-11:27 pm

2 stops12h 22m

Winnipeg

Tue 8/25

6:40 am-12:09 pm

1 stop7h 29m

$507

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 4/8

3:37 pm-1:52 pm

2 stops44h 15m

Winnipeg

Wed 4/15

6:15 am-7:07 pm

2 stops14h 52m

$521

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 4/7

3:45 pm-11:52 am

2 stops18h 07m

Winnipeg

Tue 4/14

8:45 am-9:07 pm

1 stop14h 22m

$524

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 3/4

6:30 pm-11:01 am

2 stops14h 31m

Winnipeg

Tue 3/10

5:20 pm-11:58 pm

2 stops8h 38m

$530

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sat 3/14

6:00 am-6:05 pm

2 stops10h 05m

Winnipeg

Sat 3/21

11:55 am-9:36 pm

2 stops11h 41m

$543

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sat 3/14

1:50 pm-1:52 pm

2 stops46h 02m

Winnipeg

Sat 3/21

6:55 pm-10:02 pm

2 stops29h 07m

$559

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sat 3/14

10:55 pm-11:57 am

1 stop11h 02m

Winnipeg

Sat 3/21

2:20 pm-10:59 pm

1 stop10h 39m

$597

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Thu 3/5

6:20 am-4:27 pm

1 stop8h 07m

Winnipeg

Wed 3/11

11:55 am-8:24 pm

1 stop10h 29m

$638

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Thu 3/5

6:20 am-4:27 pm

1 stop8h 07m

Winnipeg

Thu 3/12

11:55 am-11:58 pm

2 stops14h 03m

$648

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 13 results
1
2
  • 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 $112). Flying from San Jose, California to Winnipeg in December is currently the most expensive (average of $386). 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 $530, United Airlines can have you in Winnipeg from San Jose, California in 14h 31m. 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 $112). Flying from San Jose, California to Winnipeg in December is currently the most expensive (average of $386). 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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