$156+ Cheap flights from Winnipeg (YWG) to San Diego (SAN)
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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SAN
Oct 4 — Oct 111
Round-trip
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”2. Select your favorite providers
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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 Winnipeg to San Diego
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Best
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Cheapest flights from Winnipeg to San DiegoExplore 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 September 4, 2026.
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 September 4, 2026.
This FlightHub deal was found by Cheapflights users on 9/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:35 am -
1 stop7h 05m
Mon 12/71:30 pm -
1 stop8h 40m
Deal found 9/1![WestJet logo]()
$195
This United deal was found by Cheapflights users on 9/2. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:00 pm -
1 stop10h 41m
Fri 10/234:50 pm -
1 stop8h 07m
Deal found 9/2![Multiple Airlines logo]()
$242
This Air Canada deal was found by Cheapflights users on 9/2. 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.
Wed 10/215:45 am -
1 stop12h 15m
Fri 10/234:50 pm -
1 stop8h 07m
Deal found 9/2![Air Canada logo]()
$247
This United Airlines deal was found by Cheapflights users on 9/1. 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 12/28:30 am -
2 stops11h 07m
Mon 12/76:28 pm -
2 stops15h 55m
Deal found 9/1![United Airlines logo]()
$251
This United deal was found by Cheapflights users on 9/2. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:00 am -
2 stops15h 08m
Fri 10/234:50 pm -
1 stop8h 07m
Deal found 9/2![Multiple Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 11/187:35 am -
1 stop7h 05m
Thu 11/197:33 pm -
2 stops39h 17m
Deal found 9/2![Multiple Airlines logo]()
$280
This FlightHub deal was found by Cheapflights users on 9/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/94:15 pm -
2 stops47h 55m
Tue 10/133:30 pm -
1 stop7h 25m
Deal found 9/1![WestJet logo]()
$285
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Tue 9/222:00 pm -
1 stop10h 10m
Wed 9/2310:30 pm -
1 stop12h 07m
Deal found 9/3![United Airlines logo]()
$290
Best flights from Winnipeg to San DiegoDiscover carefully curated flight deals from Winnipeg to San Diego that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 4, 2026.
Discover carefully curated flight deals from Winnipeg to San Diego that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 4, 2026.
This United deal was found by Cheapflights users on 9/2. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:00 pm -
1 stop10h 41m
Fri 10/234:50 pm -
1 stop8h 07m
Deal found 9/2![Multiple Airlines logo]()
$242
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Tue 9/222:00 pm -
1 stop10h 10m
Wed 9/2312:37 pm -
2 stops22h 00m
Deal found 9/3![United Airlines logo]()
$290
This FlightHub deal was found by Cheapflights users on 9/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/17:35 am -
1 stop7h 05m
Sat 1/91:30 pm -
1 stop8h 40m
Deal found 9/2![WestJet logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 10/295:00 am -
2 stops14h 10m
Sun 11/18:32 pm -
1 stop25h 13m
Deal found 9/2![Multiple Airlines logo]()
$386
This United Airlines deal was found by Cheapflights users on 8/31. 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.
Fri 10/97:00 am -
1 stop17h 41m
Tue 10/1310:30 pm -
1 stop12h 07m
Deal found 8/31![United Airlines logo]()
$386
Last-minute flights from Winnipeg to San DiegoDiscover last-minute flight deals from Winnipeg to San Diego. Data last updated September 4, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to San Diego. Data last updated September 4, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Tue 9/222:00 pm -
1 stop10h 10m
Wed 9/2310:30 pm -
1 stop12h 07m
Deal found 9/3![United Airlines logo]()
$290
This FlightHub deal was found by Cheapflights users on 9/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/94:15 pm -
2 stops47h 55m
Tue 10/133:30 pm -
1 stop7h 25m
Deal found 9/1![WestJet logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 10/187:00 am -
1 stop9h 10m
Sun 10/252:01 pm -
2 stops25h 24m
Deal found 9/3![Multiple Airlines logo]()
$333
This United deal was found by Cheapflights users on 9/2. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:00 pm -
1 stop10h 41m
Fri 10/234:50 pm -
1 stop8h 07m
Deal found 9/2![Multiple Airlines logo]()
$242
This Air Canada deal was found by Cheapflights users on 9/2. 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.
Wed 10/215:45 am -
1 stop12h 15m
Fri 10/234:50 pm -
1 stop8h 07m
Deal found 9/2![Air Canada logo]()
$247
This United deal was found by Cheapflights users on 9/2. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:00 am -
2 stops15h 08m
Fri 10/234:50 pm -
1 stop8h 07m
Deal found 9/2![Multiple Airlines logo]()
$252
One-way flights from Winnipeg to San DiegoSearch for one-way flight options from Winnipeg to San Diego. Find affordable one-way fares based on user searches. Data last updated September 4, 2026.
Search for one-way flight options from Winnipeg to San Diego. Find affordable one-way fares based on user searches. Data last updated September 4, 2026.
This United Airlines deal was found by Cheapflights users on 9/2. 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.
Tue 10/202:00 pm -
1 stop10h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![United Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 10/206:00 am -
2 stops28h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 8/31. 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 10/3012:10 pm -
2 stops32h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![Multiple Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 8/31. 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 10/154:55 pm -
2 stops22h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![Multiple Airlines logo]()
$235
This Trip.com deal was found by Cheapflights users on 8/31. 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.
Fri 10/3012:10 pm -
1 stop27h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![WestJet logo]()
$290
This Trip.com deal was found by Cheapflights users on 8/31. 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 10/157:00 am -
1 stop9h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![WestJet logo]()
$317
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 September 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $195 (FlightHub) |
One-way from | $156 (United Airlines) |
Popular in | February |
Cheapest in | March |
Average price | $464 |
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 7,457,451 searches. Data last updated September 4, 2026.
Use the filters below to find and compare flights from Winnipeg to San Diego that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
WinnipegSan Diego
YWG Winnipeg - SAN San Diego
YWGSAN
Winnipeg
Tue 10/20
2:00 pm-10:41 pm
1 stop10h 41m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$156
WinnipegSan Diego
YWG Winnipeg - SAN San Diego
YWGSAN
Winnipeg
Tue 10/20
6:00 am-8:22 am
2 stops28h 22m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$189
WinnipegSan Diego
YWG Winnipeg - SAN San Diego
YWGSAN
Winnipeg
Fri 10/30
12:10 pm-6:38 pm
2 stops32h 28m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$208
WinnipegSan Diego
YWG Winnipeg - SAN San Diego
YWGSAN
Winnipeg
Thu 10/15
4:55 pm-1:16 pm
2 stops22h 21m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$235
WinnipegSan Diego
YWG Winnipeg - SAN San Diego
YWGSAN
Winnipeg
Tue 10/20
2:00 pm-10:41 pm
1 stop10h 41m
San Diego
Fri 10/23
4:50 pm-2:57 am
1 stop8h 07m
$242
WinnipegSan Diego
YWG Winnipeg - SAN San Diego
YWGSAN
Winnipeg
Tue 9/22
2:00 pm-10:10 pm
1 stop10h 10m
San Diego
Wed 9/23
12:37 pm-12:37 pm
2 stops22h 00m
$290
Quickest round-trip
WinnipegSan Diego
YWG Winnipeg - SAN San Diego
YWGSAN
Winnipeg
Thu 10/15
7:00 am-2:10 pm
1 stop9h 10m
San Diego
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$317
WinnipegSan Diego
YWG Winnipeg - SAN San Diego
YWGSAN
Winnipeg
Fri 1/1
7:35 am-12:40 pm
1 stop7h 05m
San Diego
Sat 1/9
1:30 pm-12:10 am
1 stop8h 40m
$347
WinnipegSan Diego
YWG Winnipeg - SAN San Diego
YWGSAN
Winnipeg
Thu 10/29
5:00 am-5:10 pm
2 stops14h 10m
San Diego
Sun 11/1
8:32 pm-11:45 pm
1 stop25h 13m
$386
WinnipegSan Diego
YWG Winnipeg - SAN San Diego
YWGSAN
Winnipeg
Fri 10/9
7:00 am-10:41 pm
1 stop17h 41m
San Diego
Tue 10/13
10:30 pm-12:37 pm
1 stop12h 07m
$386
Sorted by cheapest first
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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars |
- 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.
YWG-SAN
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, March is the cheapest month in which you can book a flight from Winnipeg to San Diego (average of $323). Flying from Winnipeg to San Diego in February is currently the most expensive (average of $865). 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.
How much does it cost to fly round-trip from Winnipeg to San Diego?
Airfare is below average for this route at the moment.
Winnipeg to San Diego flights typically cost between $463 and $587 in December.The cheapest round-trip price found within the last 5 days was $195 on WestJet (Dec 2-Dec 7).
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 September 4, 2026.
Get a feel of what it's like to fly with Delta and 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.
Comfort
7.8
Crew
8.5
Overall
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAaron,Oct 2024
TUS - LAX
Comfort
7.8
Crew
8.5
Overall
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAaron,Oct 2024
TUS - LAX
Comfort
7.8
Crew
8.5
Overall
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAaron,Oct 2024
TUS - LAX
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.
Traveling to a place near San Diego?
Book flights to San Diego if you plan to visit one of these locationsEl Cajon
National City
Chula Vista
Coronado
Poway
San Ysidro
La Mesa
Santee
Julian
Lemon Grove
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Winnipeg and San Diego flights
Browse other Winnipeg and San Diego flight options. Last updated on September 4, 2026.
Other flights from Winnipeg
Browse through other flights departing from Winnipeg. Flights are based on user searches made on Cheapflights and were last updated on September 4, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Other flights to San Diego
Explore flights to San Diego departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 4, 2026.
Top 2 airlines flying from Winnipeg to San Diego
Discover the top 2 airlines 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 7,457,451 searches. Data last updated September 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$263 | Average$441 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$345 | Average$503 | FlexibilityNo cancel fee | On-timeN/A |