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$165+ 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — YWG
Jul 16 — Jul 231
Wed 7/16
Wed 7/23
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 July 11, 2025.

Round-trip from

$375
(Trip.com)

One-way from

$165
(Kiwi.com)
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 July 11, 2025.

This Trip.com deal was found by Cheapflights users on 7/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/246:00 amSJC - YWG
3 stops13h 31mMultiple Airlines
Sun 8/3112:30 pmYWG - SJC
2 stops12h 28mMultiple Airlines
Deal found 7/9$375
This Delta deal was found by Cheapflights users on 7/8. 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.
Mon 7/215:40 pmSJC - YWG
2 stops15h 51mDelta
Thu 7/248:35 amYWG - SJC
1 stop6h 04mDelta
Deal found 7/8$659
This United Airlines deal was found by Cheapflights users on 7/9. 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.
Tue 7/226:24 pmSJC - YWG
1 stop16h 45mUnited Airlines
Fri 7/252:20 pmYWG - SJC
1 stop10h 19mUnited Airlines
Deal found 7/9$716
This Air Canada deal was found by Cheapflights users on 7/8. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/216:24 pmSJC - YWG
1 stop16h 45mAir Canada
Thu 7/244:25 pmYWG - SJC
1 stop6h 37mAir Canada
Deal found 7/8$922

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 July 11, 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 8/24

6:00 am-9:31 pm

3 stops13h 31m

Winnipeg

Sun 8/31

12:30 pm-10:58 pm

2 stops12h 28m

$375

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Mon 7/21

5:40 pm-11:31 am

2 stops15h 51m

Winnipeg

Thu 7/24

8:35 am-12:39 pm

1 stop6h 04m

$659

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 7/22

6:24 pm-1:09 pm

1 stop16h 45m

Winnipeg

Fri 7/25

2:20 pm-10:39 pm

1 stop10h 19m

$716

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Mon 7/21

6:24 pm-1:09 pm

1 stop16h 45m

Winnipeg

Thu 7/24

4:25 pm-9:02 pm

1 stop6h 37m

$922

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 7/15

4:22 pm-5:41 pm

2 stops23h 19m

$165

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 7/15

5:40 pm-11:31 am

2 stops15h 51m

$275

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Fri 10/3

8:05 pm-5:40 pm

2 stops19h 35m

$317

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 7/15

6:24 pm-4:13 pm

2 stops19h 49m

$568

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sun 8/3

7:00 am-10:33 pm

2 stops37h 33m

$637

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/9

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 $498). 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.

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 July 11, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and WestJet from San Jose to Winnipeg to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,951 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

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
7,951 reviews
Delta
8.0
Very good
7,951 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

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
8,846 reviews
Delta
8.0
Very good
7,951 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

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
2,924 reviews
Delta
8.0
Very good
7,951 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

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
7.1
Good
9,695 reviews
Delta
8.0
Very good
7,951 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

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 Delta is currently your cheapest option to Winnipeg, with prices starting at $659. Additional round-trip tickets that might be worth considering are offered by United Airlines and Air Canada, with the lowest prices starting at $716 and $922, respectively.

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

    $275 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on WestJet and Air Canada, with prices starting from $317 and $568, 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 $498). 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

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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 July 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$339Average$738FlexibilityNo cancel feeOn-timeN/A

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