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$188+ Cheap flights from San Jose (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 6/20. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — YWG
May 18 — May 251
Sun 5/18
Sun 5/25
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 May 13, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
2 stars

Round-trip from

$368
(Mytrip)

One-way from

$188
(Delta)
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 May 13, 2025.

This Mytrip deal was found by Cheapflights users on 5/12. 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.
Thu 6/126:00 amSJC - YWG
2 stops36h 30mMultiple Airlines
Thu 6/199:15 pmYWG - SJC
3 stops38h 51mMultiple Airlines
Deal found 5/12$368
This United Airlines deal was found by Cheapflights users on 5/12. 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 6/116:26 pmSJC - YWG
1 stop16h 43mUnited Airlines
Sat 6/144:25 pmYWG - SJC
1 stop6h 25mUnited Airlines
Deal found 5/12$771
This Delta deal was found by Cheapflights users on 5/12. 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 5/246:30 amSJC - YWG
1 stop8h 15mDelta
Sat 5/316:40 amYWG - SJC
2 stops13h 05mDelta
Deal found 5/12$783
This Air Canada deal was found by Cheapflights users on 5/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/22:31 pmSJC - YWG
2 stops20h 24mAir Canada
Mon 7/78:00 pmYWG - SJC
2 stops23h 18mAir Canada
Deal found 5/12$820
This WestJet deal was found by Cheapflights users on 5/12. 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 6/117:18 amSJC - YWG
2 stops12h 12mWestJet
Sat 6/143:15 pmYWG - SJC
2 stops8h 57mWestJet
Deal found 5/12$1,002

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 May 13, 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 6/12

6:00 am-8:30 pm

2 stops36h 30m

Winnipeg

Thu 6/19

9:15 pm-10:06 am

3 stops38h 51m

$368

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 6/11

6:26 pm-1:09 pm

1 stop16h 43m

Winnipeg

Sun 6/15

4:25 pm-8:50 pm

1 stop6h 25m

$771

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sat 5/24

6:30 am-4:45 pm

1 stop8h 15m

Winnipeg

Sat 5/31

6:40 am-5:45 pm

2 stops13h 05m

$783

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 7/2

2:31 pm-12:55 pm

2 stops20h 24m

Winnipeg

Mon 7/7

8:00 pm-5:18 pm

2 stops23h 18m

$820

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 6/11

7:18 am-9:30 pm

2 stops12h 12m

Winnipeg

Sat 6/14

3:15 pm-10:12 pm

2 stops8h 57m

$1,002

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Fri 6/20

5:55 pm-11:36 am

2 stops15h 41m

$188

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Fri 6/20

6:00 am-11:41 am

3 stops27h 41m

$196

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Fri 6/20

6:26 pm-1:09 pm

1 stop16h 43m

$359

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Fri 6/20

2:30 pm-3:31 pm

3 stops23h 01m

$743

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/13

  • Most accurate provider: When it comes to deals on San Jose-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-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Jose-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Jose-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-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 to Winnipeg?

Currently, August is the cheapest month in which you can book a flight from San Jose to Winnipeg (average of $358). Flying from San Jose to Winnipeg in December is currently the most expensive (average of $501). 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.

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated May 13, 2025.
Delta
8.0
Very good
7,949 reviews

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,949 reviews
Delta
8.0
Very good
7,949 reviews

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,726 reviews
Delta
8.0
Very good
7,949 reviews

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
WestJet
7.2
Good
2,839 reviews
Delta
8.0
Very good
7,949 reviews

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air Canada
7.0
Good
9,331 reviews
Delta
8.0
Very good
7,949 reviews

Entertainment

7.9

Food

7.3

Comfort

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

  • What are the cheapest airlines flying from San Jose to Winnipeg round-trip?

    Flying on United Airlines is currently your cheapest option to Winnipeg, with prices starting at $771. Additional round-trip tickets that might be worth considering are offered by Delta and Air Canada, with the lowest prices starting at $783 and $820, respectively.

  • What are the cheapest airlines to fly from San Jose to Winnipeg one-way?

    $188 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Air Canada and United Airlines, with prices starting from $359 and $743, respectively.

  • 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 to Winnipeg?

    Currently, August is the cheapest month in which you can book a flight from San Jose to Winnipeg (average of $358). Flying from San Jose to Winnipeg in December is currently the most expensive (average of $501). 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.

Top airline flying from San Jose to Winnipeg

Discover the top airline that operate flights from San Jose to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$339Average$738FlexibilityNo cancel feeOn-timeN/A

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