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$129+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SAN
Nov 12 — Nov 191
Wed 11/12
Wed 11/19
1 adult, Economy
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Find cheap flights from Winnipeg to San Diego 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”

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Cheapflights Tip: The best prices from Winnipeg to San Diego are usually found in January or August, booked 50 days in advance, depart on a Saturday or Wednesday and return on a Wednesday

Find 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 October 13, 2025.

This Delta deal was found by Cheapflights users on 10/11. 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 11/125:49 pmYWG - SAN
1 stop7h 51mDelta
Tue 12/169:50 amSAN - YWG
2 stops11h 54mDelta
Deal found 10/11$249
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 11/1412:55 pmYWG - SAN
2 stops12h 53mMultiple Airlines
Tue 11/187:59 pmSAN - YWG
1 stop26h 44mMultiple Airlines
Deal found 10/13$257
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 12/244:55 pmYWG - SAN
1 stop17h 55mMultiple Airlines
Wed 1/710:52 amSAN - YWG
1 stop11h 51mMultiple Airlines
Deal found 10/11$258
This United Airlines deal was found by Cheapflights users on 10/11. 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 11/128:40 amYWG - SAN
1 stop8h 20mUnited Airlines
Tue 12/165:08 pmSAN - YWG
1 stop16h 49mUnited Airlines
Deal found 10/11$264
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 12/244:55 pmYWG - SAN
1 stop17h 55mMultiple Airlines
Mon 1/1210:52 amSAN - YWG
1 stop11h 51mMultiple Airlines
Deal found 10/11$268
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 12/244:55 pmYWG - SAN
1 stop17h 55mMultiple Airlines
Sun 1/1112:40 pmSAN - YWG
1 stop10h 03mMultiple Airlines
Deal found 10/11$281
This Delta deal was found by Cheapflights users on 10/13. 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 11/112:20 pmYWG - SAN
1 stop10h 14mDelta
Sat 11/86:25 amSAN - YWG
1 stop8h 25mDelta
Deal found 10/13$286
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 12/244:55 pmYWG - SAN
1 stop17h 55mMultiple Airlines
Thu 1/88:34 amSAN - YWG
2 stops14h 05mMultiple Airlines
Deal found 10/11$287
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 12/257:30 amYWG - SAN
1 stop10h 31mMultiple Airlines
Wed 1/710:52 amSAN - YWG
1 stop11h 51mMultiple Airlines
Deal found 10/11$311

Cheap 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 October 13, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(Delta)

One-way from

$129
(Trip.com)

Popular in

November

Cheapest in

January

Average price

$429
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. 26% potential increase in price ($122 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 13, 2025.
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

Wed 11/12

6:40 am-3:27 pm

2 stops10h 47m

San Diego

Tue 12/16

9:50 am-11:44 pm

2 stops11h 54m

$249

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Wed 11/5

5:40 pm-11:27 pm

1 stop7h 47m

San Diego

Tue 11/11

7:59 pm-11:48 am

2 stops13h 49m

$250

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Sat 11/1

12:20 pm-8:34 pm

1 stop10h 14m

San Diego

Sat 11/8

10:20 pm-11:48 am

2 stops11h 28m

$250

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Fri 11/14

12:55 pm-11:48 pm

2 stops12h 53m

San Diego

Tue 11/18

7:59 pm-12:43 am

1 stop26h 44m

$257

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Wed 11/12

8:40 am-6:34 pm

2 stops11h 54m

San Diego

Tue 12/16

1:05 pm-11:57 am

2 stops20h 52m

$264

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Thu 12/25

12:35 pm-9:03 pm

1 stop10h 28m

San Diego

Thu 1/8

12:05 pm-11:33 pm

1 stop9h 28m

$341

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Mon 11/24

4:55 pm-7:44 am

1 stop16h 49m

$129

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Wed 11/26

4:55 pm-7:54 am

1 stop16h 59m

$143

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Wed 1/7

12:55 pm-9:57 am

2 stops23h 02m

$151

WinnipegSan Diego

YWG - SAN

YWGSAN

Winnipeg

Thu 1/8

2:20 pm-10:33 pm

1 stop10h 13m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/10

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 October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-San Diego flight deals on Cheapflights vs. FlightHub >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 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 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

How far ahead should I book a flight from Winnipeg to San Diego?

Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to San Diego. Price data was last updated on October 10, 2025.

The best time to book flights from Winnipeg to San Diego is 49 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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 October 13, 2025.
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
3,124 reviews

Boarding

7.4

Comfort

7.1

Entertainment

6.1

Food

6.2

Crew

7.9

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.
WestJet
7.2
Good
3,124 reviews
WestJet
7.2
Good
3,124 reviews

Boarding

7.4

Comfort

7.1

Entertainment

6.1

Food

6.2

Crew

7.9

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.

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 10h 47m. Delta provides one of the quickest options available for as low as $249. There are 1564 mi between Winnipeg and San Diego.

  • 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 44% lower than the current average price of a flight leaving 3 months from now.

  • 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
Coronado
La Mesa
Poway
Lemon Grove
Imperial Beach
National City

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 October 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$187Average$296FlexibilityNo cancel feeOn-time60%

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