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$150+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — YWG
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap 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 January 26, 2026.

This Trip.com deal was found by Cheapflights users on 1/26. 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.
Wed 4/293:30 pm
SAN
-
YWG
1 stop7h 25m
WestJet
Mon 5/47:00 am
YWG
-
SAN
1 stop9h 10m
WestJet
Deal found 1/26$303
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Thu 3/52:38 pm
SAN
-
YWG
2 stops21h 14m
Multiple Airlines
Mon 3/96:15 am
YWG
-
SAN
1 stop7h 32m
Multiple Airlines
Deal found 1/26$312
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 3/22:00 pm
SAN
-
YWG
2 stops19h 32m
Multiple Airlines
Mon 3/96:15 am
YWG
-
SAN
1 stop7h 32m
Multiple Airlines
Deal found 1/26$320
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Tue 3/38:00 am
SAN
-
YWG
2 stops14h 41m
Multiple Airlines
Mon 3/96:15 am
YWG
-
SAN
1 stop7h 32m
Multiple Airlines
Deal found 1/26$327
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/278:18 pm
SAN
-
YWG
2 stops13h 14m
Multiple Airlines
Mon 3/96:15 am
YWG
-
SAN
1 stop7h 32m
Multiple Airlines
Deal found 1/26$330
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Thu 3/52:38 pm
SAN
-
YWG
2 stops21h 14m
Multiple Airlines
Sun 3/86:55 pm
YWG
-
SAN
1 stop18h 52m
Multiple Airlines
Deal found 1/26$337
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Sun 3/18:20 pm
SAN
-
YWG
2 stops39h 32m
Multiple Airlines
Mon 3/98:00 am
YWG
-
SAN
1 stop27h 51m
Multiple Airlines
Deal found 1/26$341
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 3/22:00 pm
SAN
-
YWG
2 stops19h 32m
Multiple Airlines
Sun 3/86:55 pm
YWG
-
SAN
1 stop18h 52m
Multiple Airlines
Deal found 1/26$345
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Wed 2/258:59 pm
SAN
-
YWG
1 stop16h 13m
Multiple Airlines
Sat 2/285:55 am
YWG
-
SAN
2 stops15h 58m
Multiple Airlines
Deal found 1/26$350
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Tue 3/38:00 am
SAN
-
YWG
2 stops14h 41m
Multiple Airlines
Sun 3/86:55 pm
YWG
-
SAN
1 stop18h 52m
Multiple Airlines
Deal found 1/26$352
This United Airlines deal was found by Cheapflights users on 1/23. 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.
Mon 3/911:03 am
SAN
-
YWG
2 stops22h 54m
United Airlines
Wed 3/112:20 pm
YWG
-
SAN
1 stop10h 20m
United Airlines
Deal found 1/23$354

Find 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 January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$303
(Trip.com)

One-way from

$150
(Kiwi.com)

Popular in

January

Cheapest in

March

Average price

$1,066
Provider with most accurate pricing for San Diego-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Diego-Winnipeg flights.
Search Deals
From San Diego to Winnipeg
Search Deals
One-way flight from San Diego to Winnipeg
Search Deals
Highest demand for flights based on searches. 40% potential increase in price ($336 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 13% potential price decrease ($58 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 26, 2026.
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

Mon 3/9

11:03 am-11:57 am

2 stops22h 54m

Winnipeg

Wed 3/11

2:20 pm-10:40 pm

1 stop10h 20m

$354

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Thu 3/5

2:38 pm-1:52 pm

2 stops21h 14m

Winnipeg

Tue 3/10

9:00 pm-11:47 am

1 stop16h 47m

$357

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Mon 4/6

10:30 pm-11:52 am

1 stop11h 22m

Winnipeg

Mon 4/13

2:00 pm-10:59 pm

1 stop10h 59m

$385

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Thu 3/12

10:30 pm-11:57 am

1 stop11h 27m

Winnipeg

Mon 3/16

2:20 pm-9:20 am

2 stops21h 00m

$395

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Fri 2/27

8:18 pm-11:32 am

2 stops13h 14m

$150

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Wed 3/25

2:50 pm-8:33 am

3 stops39h 43m

$154

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Fri 2/27

5:00 pm-11:57 am

1 stop16h 57m

$165

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Mon 3/2

5:00 pm-11:57 am

1 stop16h 57m

$166

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Wed 3/25

10:30 pm-11:57 am

1 stop11h 27m

$171

San DiegoWinnipeg

SAN - YWG

SANYWG

San Diego

Fri 4/10

10:30 pm-11:52 am

1 stop11h 22m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

Showing 1-10 of 12 results
1
2

Compare providers for flights from San Diego to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Diego to Winnipeg in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy2 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Trip.comPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on San Diego-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Diego-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Diego-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Diego-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 Diego-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 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, March is the cheapest month in which you can book a flight from San Diego to Winnipeg (average of $114). Flying from San Diego to Winnipeg in May is currently the most expensive (average of $437). 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 January 26, 2026.
Get a feel of what it's like to fly with Delta, WestJet, and Air Canada 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
7.9
Good
8,113 reviews

Entertainment

7.8

Comfort

7.9

Food

7.2

Boarding

8.1

Overall

7.9

Crew

8.5

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
7.9
Good
8,113 reviews
Delta
7.9
Good
8,113 reviews

Entertainment

7.8

Comfort

7.9

Food

7.2

Boarding

8.1

Overall

7.9

Crew

8.5

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
3,249 reviews
Delta
7.9
Good
8,113 reviews

Entertainment

7.8

Comfort

7.9

Food

7.2

Boarding

8.1

Overall

7.9

Crew

8.5

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
10,656 reviews
Delta
7.9
Good
8,113 reviews

Entertainment

7.8

Comfort

7.9

Food

7.2

Boarding

8.1

Overall

7.9

Crew

8.5

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.

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

    For as low as $354, United Airlines can have you in Winnipeg from San Diego in 22h 54m. There are 1564 mi between San Diego and Winnipeg.

  • What are the cheapest airlines flying from San Diego to Winnipeg round-trip?

    Delta, at $143, was found to be the cheapest airline from San Diego to Winnipeg.Alternate airlines to your destination round-trip include WestJet and Air Canada. Delta is priced at 70% lower than the current average price of a flight leaving 3 months from now.

  • 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, March is the cheapest month in which you can book a flight from San Diego to Winnipeg (average of $114). Flying from San Diego to Winnipeg in May is currently the most expensive (average of $437). 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 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 January 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$143Average$487FlexibilityNo cancel feeOn-timeN/A
WestJetCheapest$192Average$348FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$402Average$494FlexibilityNo cancel feeOn-time67%

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