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$812+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — YWG
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
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 August 18, 2025.

Round-trip from

$812
(Mytrip)
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 August 18, 2025.

This Mytrip deal was found by Cheapflights users on 8/17. 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.
Sat 8/3012:39 pmSJC - YWG
3 stops21h 02mMultiple Airlines
Tue 9/28:15 pmYWG - SJC
2 stops28h 15mMultiple Airlines
Deal found 8/17$812
This Delta deal was found by Cheapflights users on 8/17. 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 8/3010:25 pmSJC - YWG
2 stops11h 26mDelta
Tue 9/28:30 amYWG - SJC
2 stops11h 00mDelta
Deal found 8/17$896
This Mytrip deal was found by Cheapflights users on 8/16. 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 8/2912:39 pmSJC - YWG
2 stops30h 47mMultiple Airlines
Mon 9/18:30 amYWG - SJC
2 stops33h 16mMultiple Airlines
Deal found 8/16$968
This FlightHub deal was found by Cheapflights users on 8/16. 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 8/277:23 amSJC - YWG
2 stops12h 08mWestJet
Fri 8/2910:00 amYWG - SJC
2 stops14h 49mWestJet
Deal found 8/16$1,006
This United Airlines deal was found by Cheapflights users on 8/16. 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 8/276:30 amSJC - YWG
1 stop14h 03mUnited Airlines
Fri 8/292:20 pmYWG - SJC
1 stop10h 20mUnited Airlines
Deal found 8/16$1,094
This Delta deal was found by Cheapflights users on 8/16. 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 8/297:00 amSJC - YWG
2 stops14h 27mDelta
Mon 9/16:40 amYWG - SJC
1 stop7h 41mDelta
Deal found 8/16$1,135
This Delta deal was found by Cheapflights users on 8/16. 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 8/271:20 pmSJC - YWG
1 stop8h 07mDelta
Fri 8/296:40 amYWG - SJC
2 stops12h 24mDelta
Deal found 8/16$1,271

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 August 18, 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

Sat 8/30

12:39 pm-11:41 am

3 stops21h 02m

Winnipeg

Tue 9/2

8:15 pm-10:30 pm

2 stops28h 15m

$812

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sat 8/30

10:25 pm-11:51 am

2 stops11h 26m

Winnipeg

Tue 9/2

8:30 am-5:30 pm

2 stops11h 00m

$896

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Fri 8/29

12:39 pm-9:26 pm

2 stops30h 47m

Winnipeg

Mon 9/1

8:30 am-3:46 pm

2 stops33h 16m

$968

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 8/27

7:23 am-9:31 pm

2 stops12h 08m

Winnipeg

Fri 8/29

10:00 am-10:49 pm

2 stops14h 49m

$1,006

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 8/27

6:30 am-10:33 pm

1 stop14h 03m

Winnipeg

Fri 8/29

2:20 pm-10:40 pm

1 stop10h 20m

$1,094

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Fri 8/29

7:00 am-11:27 pm

2 stops14h 27m

Winnipeg

Mon 9/1

6:40 am-12:21 pm

1 stop7h 41m

$1,135

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 8/27

1:20 pm-11:27 pm

1 stop8h 07m

Winnipeg

Fri 8/29

6:40 am-5:04 pm

2 stops12h 24m

$1,271

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

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 $495). 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 August 18, 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
7,981 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.2

Overall

8.0

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
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.2

Overall

8.0

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 can get you from San Jose to Winnipeg in just under 11h 26m. Your travel time can differ by up to . San Jose and Winnipeg are separated by a distance of 1496 mi.

  • 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 $339.

  • 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 $495). 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

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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$339Average$738FlexibilityNo cancel feeOn-timeN/A

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