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$373+ Cheap flights from San Jose (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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — YWG
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$777
(Air Canada)
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 September 15, 2025.

This Mytrip deal was found by Cheapflights users on 9/12. 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.
Fri 9/266:35 amSJC - YWG
3 stops12h 55mMultiple Airlines
Mon 9/293:15 pmYWG - SJC
2 stops21h 30mMultiple Airlines
Deal found 9/12$373
This Delta deal was found by Cheapflights users on 9/12. 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.
Fri 9/265:55 amSJC - YWG
2 stops15h 32mDelta
Mon 9/296:40 amYWG - SJC
2 stops14h 33mDelta
Deal found 9/12$537
This United Airlines deal was found by Cheapflights users on 9/12. 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.
Fri 9/268:45 amSJC - YWG
1 stop26h 24mUnited Airlines
Mon 9/297:00 pmYWG - SJC
2 stops43h 01mUnited Airlines
Deal found 9/12$738
This Mytrip deal was found by Cheapflights users on 9/13. 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.
Wed 9/173:26 pmSJC - YWG
2 stops24h 49mMultiple Airlines
Thu 9/259:00 amYWG - SJC
3 stops32h 21mMultiple Airlines
Deal found 9/13$855
This FlightHub deal was found by Cheapflights users on 9/13. 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.
Tue 9/168:12 pmSJC - YWG
2 stops19h 28mWestJet
Tue 9/236:15 pmYWG - SJC
2 stops30h 40mWestJet
Deal found 9/13$1,074
This FlightHub deal was found by Cheapflights users on 9/13. 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.
Wed 9/179:02 amSJC - YWG
2 stops30h 23mWestJet
Wed 9/2410:00 amYWG - SJC
2 stops14h 55mWestJet
Deal found 9/13$1,083
This FlightHub deal was found by Cheapflights users on 9/13. 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.
Tue 9/169:02 amSJC - YWG
2 stops9h 13mWestJet
Wed 9/2410:00 amYWG - SJC
2 stops14h 55mWestJet
Deal found 9/13$1,091
This Air Canada deal was found by Cheapflights users on 9/13. 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 9/176:20 pmSJC - YWG
1 stop16h 49mAir Canada
Wed 9/245:00 amYWG - SJC
2 stops14h 17mAir Canada
Deal found 9/13$1,149

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 September 15, 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

Fri 9/26

6:35 am-9:30 pm

3 stops12h 55m

Winnipeg

Mon 9/29

3:15 pm-10:45 am

2 stops21h 30m

$373

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Fri 9/26

5:55 am-11:27 pm

2 stops15h 32m

Winnipeg

Mon 9/29

6:40 am-7:13 pm

2 stops14h 33m

$537

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Fri 9/26

8:45 am-1:09 pm

1 stop26h 24m

Winnipeg

Mon 9/29

7:00 pm-12:01 pm

2 stops43h 01m

$738

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 3/3

8:25 am-1:09 am

2 stops14h 44m

Winnipeg

Wed 3/4

6:00 am-9:11 pm

2 stops17h 11m

$777

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 3/10

8:25 am-9:44 pm

2 stops11h 19m

Winnipeg

Wed 3/11

6:00 am-5:43 pm

2 stops13h 43m

$824

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

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.

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 September 15, 2025.
Peruse reviews from past customers who have flown with Delta 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
7,954 reviews

Entertainment

7.9

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

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
7,954 reviews
Delta
8.0
Very good
7,954 reviews

Entertainment

7.9

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

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.

  • How long is the flight from San Jose to Winnipeg?

    Delta, United Airlines, and Air Canada can get you from San Jose to Winnipeg in just under 14h 44m. Your travel time can differ by up to 11h 40m. San Jose and Winnipeg are separated by a distance of 1496 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What is the cheapest airline to fly from San Jose to Winnipeg round-trip?

    Flying on Delta is currently your cheapest option to Winnipeg, with prices starting at $719.

  • 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

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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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$719Average$758FlexibilityNo cancel feeOn-timeN/A

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