HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Winnipeg

$432+ Cheap flights from San Jose, CA (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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — YWG
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from San Jose to Winnipeg with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$432
(United Airlines)
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

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 October 16, 2025.

This Delta deal was found by Cheapflights users on 10/15. 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 11/126:15 amSJC - YWG
1 stop8h 44mDelta
Sun 11/166:40 amYWG - SJC
1 stop7h 28mDelta
Deal found 10/15$432
This Mytrip deal was found by Cheapflights users on 10/15. 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 11/123:37 pmSJC - YWG
3 stops31h 02mMultiple Airlines
Sun 11/168:30 pmYWG - SJC
2 stops24h 52mMultiple Airlines
Deal found 10/15$705
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Sat 10/186:30 amSJC - YWG
1 stop14h 03mUnited Airlines
Sat 11/12:20 pmYWG - SJC
1 stop10h 08mUnited Airlines
Deal found 10/16$1,007
This Delta deal was found by Cheapflights users on 10/16. 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.
Sat 10/186:20 amSJC - YWG
1 stop8h 30mDelta
Fri 10/317:50 amYWG - SJC
2 stops15h 41mDelta
Deal found 10/16$1,012
This Delta deal was found by Cheapflights users on 10/16. 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.
Thu 10/168:10 pmSJC - YWG
2 stops13h 20mDelta
Sun 11/25:40 amYWG - SJC
1 stop7h 44mDelta
Deal found 10/16$1,016
This Delta deal was found by Cheapflights users on 10/16. 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.
Thu 10/168:10 pmSJC - YWG
2 stops13h 20mDelta
Thu 10/306:40 amYWG - SJC
2 stops10h 07mDelta
Deal found 10/16$1,021
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2012:38 pmSJC - YWG
2 stops30h 47mMultiple Airlines
Mon 11/38:00 amYWG - SJC
1 stop11h 34mMultiple Airlines
Deal found 10/16$1,025
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/177:00 amSJC - YWG
2 stops33h 15mMultiple Airlines
Mon 11/38:00 amYWG - SJC
1 stop11h 34mMultiple Airlines
Deal found 10/16$1,034

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 October 16, 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

Tue 3/10

10:40 pm-11:39 am

1 stop10h 59m

Winnipeg

Wed 3/11

2:15 pm-10:30 pm

1 stop10h 15m

$432

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 11/12

6:15 am-4:59 pm

1 stop8h 44m

Winnipeg

Sun 11/16

6:40 am-6:19 pm

2 stops13h 39m

$441

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Wed 11/12

3:37 pm-12:39 am

3 stops31h 02m

Winnipeg

Sun 11/16

8:30 pm-7:22 pm

2 stops24h 52m

$705

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Tue 3/10

11:35 am-10:40 pm

2 stops9h 05m

Winnipeg

Wed 3/11

6:15 am-2:57 pm

2 stops10h 42m

$878

San JoseWinnipeg

SJC - YWG

SJCYWG

San Jose

Sun 12/21

10:30 pm-11:57 am

1 stop11h 27m

Winnipeg

Sun 12/28

8:40 am-1:33 pm

1 stop6h 53m

$1,169

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

  • 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, February is the cheapest month in which you can book a flight from San Jose, California to Winnipeg (average of $114). Flying from San Jose, California to Winnipeg in November is currently the most expensive (average of $273). 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 October 16, 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
7,984 reviews

Overall

8.0

Comfort

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

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
7,984 reviews
Delta
8.0
Very good
7,984 reviews

Overall

8.0

Comfort

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

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, California to Winnipeg?

    For as low as $441, United Airlines can have you in Winnipeg from San Jose, California in 8h 44m. There are 1496 mi between San Jose, California and Winnipeg. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Currently priced at $719, Delta will fly you from San Jose, California to Winnipeg and back. In addition to Delta, many other airlines offer competitively priced options for your trip.

  • 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, February is the cheapest month in which you can book a flight from San Jose, California to Winnipeg (average of $114). Flying from San Jose, California to Winnipeg in November is currently the most expensive (average of $273). 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

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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$719Average$758FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.