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San Diego

$187+ Cheap flights from Winnipeg (YWG) to San Diego (SAN)

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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SAN
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from Winnipeg to San Diego

Cheapest flights from Winnipeg to San Diego
Explore the most affordable flight options available from Winnipeg to San Diego. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This United Airlines deal was found by Cheapflights users on 1/20. 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 4/92:00 pm
YWG
-
SAN
2 stops22h 20m
United Airlines
Mon 4/1311:01 am
SAN
-
YWG
2 stops22h 51m
United Airlines
Deal found 1/20$319
This United Airlines deal was found by Cheapflights users on 1/20. 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 3/52:20 pm
YWG
-
SAN
2 stops20h 20m
United Airlines
Sun 3/810:30 pm
SAN
-
YWG
1 stop11h 27m
United Airlines
Deal found 1/20$326
This Delta deal was found by Cheapflights users on 1/20. 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.
Mon 3/211:53 am
YWG
-
SAN
1 stop11h 00m
Delta
Wed 3/412:00 pm
SAN
-
YWG
1 stop9h 36m
Delta
Deal found 1/20$362
This Trip.com deal was found by Cheapflights users on 1/21. 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 9/108:30 am
YWG
-
SAN
1 stop6h 50m
WestJet
Sun 9/202:05 pm
SAN
-
YWG
1 stop6h 55m
WestJet
Deal found 1/21$392
This Delta deal was found by Cheapflights users on 1/20. 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.
Tue 2/1711:53 am
YWG
-
SAN
1 stop11h 00m
Delta
Tue 2/243:20 pm
SAN
-
YWG
2 stops17h 41m
Delta
Deal found 1/20$414
This Air Canada deal was found by Cheapflights users on 1/20. 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 3/56:00 am
YWG
-
SAN
1 stop8h 03m
Air Canada
Sun 3/810:30 pm
SAN
-
YWG
1 stop11h 27m
Air Canada
Deal found 1/20$419
This United Airlines deal was found by Cheapflights users on 1/19. 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 3/22:20 pm
YWG
-
SAN
2 stops22h 04m
United Airlines
Wed 3/44:00 pm
SAN
-
YWG
2 stops17h 57m
United Airlines
Deal found 1/19$421
This United Airlines deal was found by Cheapflights users on 1/21. 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.
Sun 3/152:20 pm
YWG
-
SAN
1 stop10h 20m
United Airlines
Thu 3/198:50 pm
SAN
-
YWG
2 stops13h 07m
United Airlines
Deal found 1/21$444

Find flight deals from Winnipeg to San Diego

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to San Diego (SAN). 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 21, 2026.

Most accurate provider

oojo
3 stars

Most trusted provider

oojo
3 stars

Round-trip from

$319
(United Airlines)

One-way from

$187
(United Airlines)

Popular in

October

Cheapest in

August

Average price

$330
Provider with most accurate pricing for Winnipeg-San Diego flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-San Diego flights.
Search Deals
From Winnipeg to San Diego
Search Deals
One-way flight from Winnipeg to San Diego
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 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 Winnipeg to San Diego 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 21, 2026.
Use the filters below to find and compare flights from Winnipeg to San Diego that are best for you.

Fly from

Winnipeg

Fly to

San Diego

Route

Depart

Return

Price

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Thu 4/9

2:00 pm-10:20 am

2 stops22h 20m

San Diego

Mon 4/13

11:01 am-11:52 am

2 stops22h 51m

$319

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Mon 3/2

11:53 am-8:53 pm

1 stop11h 00m

San Diego

Wed 3/4

12:00 pm-11:36 pm

1 stop9h 36m

$319

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Thu 3/5

2:20 pm-8:40 am

2 stops20h 20m

San Diego

Sun 3/8

10:30 pm-11:57 am

1 stop11h 27m

$326

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Tue 2/17

11:53 am-8:53 pm

1 stop11h 00m

San Diego

Tue 2/24

3:20 pm-11:01 am

2 stops17h 41m

$414

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Thu 3/5

6:00 am-12:03 pm

1 stop8h 03m

San Diego

Sun 3/8

10:30 pm-11:57 am

1 stop11h 27m

$419

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Mon 3/2

2:20 pm-10:24 am

2 stops22h 04m

San Diego

Wed 3/4

4:00 pm-11:57 am

2 stops17h 57m

$421

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Fri 3/6

2:20 pm-11:40 pm

2 stops11h 20m

$187

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Sat 2/28

8:30 pm-1:05 pm

2 stops42h 35m

$192

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Fri 3/6

4:10 pm-12:09 am

3 stops33h 59m

$210

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Fri 3/6

11:53 am-8:53 pm

1 stop11h 00m

$244

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 13 results
1
2

Compare providers for flights from Winnipeg to San Diego

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 Winnipeg to San Diego in January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars
oojoPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy2 starsTrust 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 Winnipeg-San Diego flights, users find the pricing of oojo to be most consistent on Cheapflights vs. oojo Users can find the same prices on Winnipeg-San Diego flight deals on Cheapflights vs. oojo >95% of the time. Price accuracy is based on data collected from Winnipeg-San Diego flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Winnipeg-San Diego flights, Cheapflights users trust oojo the most. oojo 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 Winnipeg-San Diego 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 Winnipeg to San Diego

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

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

Currently, June is the cheapest month in which you can book a flight from Winnipeg to San Diego (average of $121). Flying from Winnipeg to San Diego in August is currently the most expensive (average of $223). 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 San Diego

Get insights into the airlines that provide service to San Diego. 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 San Diego. Reviews last updated January 21, 2026.
Get a feel of what it's like to fly with WestJet from Winnipeg to San Diego by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,247 reviews

Crew

7.9

Food

6.2

Entertainment

6.1

Boarding

7.4

Comfort

7.0

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying
WestJet
7.2
Good
3,247 reviews
WestJet
7.2
Good
3,247 reviews

Crew

7.9

Food

6.2

Entertainment

6.1

Boarding

7.4

Comfort

7.0

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Blaine,Dec 2025

YYC - YVR

The worst I’ve ever had in 50 years of flying

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to San Diego. 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 Winnipeg to San Diego?

    A quick flight from Winnipeg to San Diego can take about 11h. United Airlines provides one of the quickest options available for as low as $319. There are 1564 mi between Winnipeg and San Diego. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Our cheapest airline available from Winnipeg to San Diego is WestJet. Our recent data shows that you can find tickets from as low as $187 on this airline. WestJet is priced at 42% lower than the current average price of a flight leaving 3 months from now.

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

    One-way options have recently been found by users for as low as $167 on Delta. Other airlines that offer cheap prices include United Airlines from $167 and Air Canada from $241 one-way.

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

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

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

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

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

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

    Currently, June is the cheapest month in which you can book a flight from Winnipeg to San Diego (average of $121). Flying from Winnipeg to San Diego in August is currently the most expensive (average of $223). 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 San Diego?

Book flights to San Diego if you plan to visit one of these locations
El Cajon
Chula Vista
National City
Coronado
La Mesa
Poway
Julian
Lemon Grove

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Winnipeg to San Diego

Discover the top airline that operate flights from Winnipeg to San Diego. 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 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$187Average$328FlexibilityNo cancel feeOn-time60%

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