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$105+ Cheap flights from San Diego (SAN) 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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — YWG
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheap flight deals from San Diego to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from San Diego (SAN) 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 29, 2025.

Round-trip from

$243
(Trip.com)

One-way from

$105
(Trip.com)

Popular in

January

Cheapest in

March

Average price

$348
From San Diego to Winnipeg
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One-way flight from San Diego to Winnipeg
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Highest demand for flights based on searches. 27% potential increase in price ($188 potential increase over avg. RT price).
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Cheapest flight prices on average. 15% potential price decrease ($65 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from San Diego to Winnipeg

Cheapest flights from San Diego to Winnipeg
Explore the most affordable flight options available from San Diego to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

This Trip.com deal was found by Cheapflights users on 7/27. 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.
Thu 9/112:05 pmSAN - YWG
1 stop8h 25mWestJet
Sun 9/148:30 amYWG - SAN
1 stop6h 50mWestJet
Deal found 7/27$243
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 9/126:25 amSAN - YWG
2 stops29h 48mMultiple Airlines
Fri 9/196:30 amYWG - SAN
1 stop8h 50mMultiple Airlines
Deal found 7/29$334
This Air Canada deal was found by Cheapflights users on 7/27. 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.
Thu 10/234:40 pmSAN - YWG
1 stop7h 07mAir Canada
Tue 10/286:00 amYWG - SAN
1 stop8h 03mAir Canada
Deal found 7/27$336
This United Airlines deal was found by Cheapflights users on 7/27. 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.
Thu 10/2310:30 pmSAN - YWG
1 stop15h 01mUnited Airlines
Tue 10/288:40 amYWG - SAN
2 stops11h 54mUnited Airlines
Deal found 7/27$360
This Delta deal was found by Cheapflights users on 7/27. 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 10/237:03 pmSAN - YWG
2 stops14h 27mDelta
Tue 10/2812:20 pmYWG - SAN
2 stops13h 28mDelta
Deal found 7/27$366

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Diego 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 29, 2025.
Use the filters below to find and compare flights from San Diego to Winnipeg that are best for you.

Fly from

San Diego

Fly to

Winnipeg

Route

Depart

Return

Price

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Thu 9/11

2:05 pm-12:30 am

1 stop8h 25m

Winnipeg

Sun 9/14

8:30 am-1:20 pm

1 stop6h 50m

$243

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Thu 10/23

4:40 pm-1:47 am

1 stop7h 07m

Winnipeg

Tue 10/28

6:00 am-12:03 pm

1 stop8h 03m

$336

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Fri 9/5

6:35 am-8:15 pm

2 stops11h 40m

Winnipeg

Mon 9/8

8:30 am-1:20 pm

1 stop6h 50m

$346

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Thu 10/23

10:30 pm-3:31 pm

1 stop15h 01m

Winnipeg

Tue 10/28

8:40 am-6:34 pm

2 stops11h 54m

$360

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Thu 10/23

7:03 pm-11:30 am

2 stops14h 27m

Winnipeg

Tue 10/28

12:20 pm-11:48 pm

2 stops13h 28m

$366

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Wed 10/8

2:05 pm-11:10 pm

1 stop7h 05m

$105

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Thu 10/9

9:03 pm-8:15 pm

2 stops21h 12m

$123

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Tue 10/7

4:40 pm-1:47 am

1 stop7h 07m

$144

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Fri 8/29

10:30 pm-3:31 pm

1 stop15h 01m

$161

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Tue 10/7

7:40 am-4:48 pm

1 stop7h 08m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Best time to book a flight from San Diego to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from San Diego 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 Diego to Winnipeg

What is the cheapest month to book a flight from San Diego to Winnipeg?

Currently, August is the cheapest month in which you can book a flight from San Diego to Winnipeg (average of $358). Flying from San Diego to Winnipeg in December is currently the most expensive (average of $497). 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.

What’s the top layover airport for flights from San Diego to Winnipeg?

Share of 1-stop round-trip flights from San Diego to Winnipeg chosen by Cheapflights users in the past 12 months, using the same layover each way.

Calgary (YYC) – chosen by Cheapflights users on 86% of 1-stop itineraries from San Diego to Winnipeg on Cheapflights.

What’s the cheapest layover airport for flights from San Diego to Winnipeg?

Average round-trip fare for 1-stop flights from San Diego to Winnipeg, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of $395.

What’s the fastest layover option from San Diego to Winnipeg?

Shortest average travel time for 1-stop one-way flights from San Diego to Winnipeg, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Calgary (YYC) have the shortest average one-way travel time for 1-stop routes: 3h 45m.

Which airport typically offers the quickest layover for flights from San Diego to Winnipeg?

Average layover duration for 1-stop one-way flights from San Diego to Winnipeg, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Calgary (YYC) offer the fastest connection on this route, with an average layover time of 1h 31m.

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 29, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and WestJet from San Diego to Winnipeg by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,979 reviews

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

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
7,979 reviews
Delta
8.0
Very good
7,979 reviews

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

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
8,896 reviews
Delta
8.0
Very good
7,979 reviews

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

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
2,972 reviews
Delta
8.0
Very good
7,979 reviews

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

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
7.1
Good
9,826 reviews
Delta
8.0
Very good
7,979 reviews

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

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 Diego 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 Diego to Winnipeg round-trip?

    WestJet, at $243, was found to be the cheapest airline from San Diego to Winnipeg.Alternate airlines to your destination round-trip include Air Canada and United Airlines. WestJet is priced at 50% lower than the current average price of a flight leaving 3 months from now.

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

    The cheapest airlines for a one-way flight from San Diego to Winnipeg are WestJet ($105), Air Canada ($144), and United Airlines ($161).

  • Can I find deals for flights from San Diego to Winnipeg that include hotel bookings?

    Yes. In addition to deals on San Diego to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Diego to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Diego to Winnipeg.

  • Can I find deals for business class flights from San Diego to Winnipeg?

    Yes. Cheapflights offers flight deals from San Diego 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 Diego to Winnipeg?

    Currently, August is the cheapest month in which you can book a flight from San Diego to Winnipeg (average of $358). Flying from San Diego to Winnipeg in December is currently the most expensive (average of $497). 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 3 airlines flying from San Diego to Winnipeg

Discover the top 3 airlines that operate flights from San Diego 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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$205Average$468FlexibilityNo cancel feeOn-timeN/A
WestJetCheapest$236Average$348FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$402Average$443FlexibilityNo cancel feeOn-time67%

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