YWG - SAN

C$ 258 Find Cheap Flights from Winnipeg to San Diego – Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to San Diego departing on 14/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
C$ 403
Typical prices: C$ 422-C$ 591
WestJet
Fri 9/10Tue 13/10
YWG - SAN • 2 stops
Cheapest one-way flights
C$ 258
Typical prices: C$ 255-C$ 1,040
Multiple Airlines
Mon 14/9
YWG - SAN • 3 stops
Top airlines
Cheapest • from C$ 403 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Direct flights
Not available
There are currently no direct flights between Winnipeg and San Diego. You’ll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg C$ 530 (round-trip)
Shortest trip • 8h 18m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 23% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to San Diego!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Winnipeg to San Diego (YWG-SAN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to San Diego that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Winnipeg to San Diego

Fri, 9 Oct - Tue, 13 Oct
WestJet Logo
4:15 p.m. - 2:10 p.m.
YWG
-
SAN
47h 55m
2 stops
WestJet Logo
3:30 p.m. - 12:55 a.m.
SAN
-
YWG
7h 25m
1 stop
C$ 403WestJet
Fri, 9 Oct - Tue, 13 Oct
Multiple Airlines Logo
7:00 a.m. - 12:40 p.m.
YWG
-
SAN
31h 40m
2 stops
Multiple Airlines Logo
3:30 p.m. - 12:55 a.m.
SAN
-
YWG
7h 25m
1 stop
C$ 404Multiple Airlines
Tue, 22 Sep - Fri, 25 Sep
WestJet Logo
7:00 a.m. - 2:10 p.m.
YWG
-
SAN
9h 10m
1 stop
WestJet Logo
3:30 p.m. - 12:55 a.m.
SAN
-
YWG
7h 25m
1 stop
C$ 438WestJet
Fri, 9 Oct - Tue, 13 Oct
WestJet Logo
10:30 p.m. - 2:10 p.m.
YWG
-
SAN
41h 40m
2 stops
WestJet Logo
3:30 p.m. - 9:20 a.m.
SAN
-
YWG
15h 50m
2 stops
C$ 442WestJet
Mon, 21 Sep - Sun, 27 Sep
WestJet Logo
7:00 a.m. - 2:10 p.m.
YWG
-
SAN
9h 10m
2 stops
WestJet Logo
3:30 p.m. - 12:55 a.m.
SAN
-
YWG
7h 25m
1 stop
C$ 445WestJet
Mon, 7 Sep - Mon, 14 Sep
Multiple Airlines Logo
7:00 a.m. - 2:10 p.m.
YWG
-
SAN
9h 10m
1 stop
Multiple Airlines Logo
9:03 p.m. - 10:10 p.m.
SAN
-
YWG
23h 07m
2 stops
C$ 449Multiple Airlines
Mon, 21 Sep - Sun, 27 Sep
WestJet Logo
7:00 a.m. - 2:10 p.m.
YWG
-
SAN
9h 10m
1 stop
WestJet Logo
3:30 p.m. - 11:10 a.m.
SAN
-
YWG
17h 40m
1 stop
C$ 460WestJet
Mon, 14 Sep - Wed, 23 Sep
WestJet Logo
7:00 a.m. - 2:10 p.m.
YWG
-
SAN
9h 10m
1 stop
WestJet Logo
3:30 p.m. - 12:55 a.m.
SAN
-
YWG
7h 25m
1 stop
C$ 477WestJet
Thu, 3 Dec - Wed, 9 Dec
Delta Logo
12:30 p.m. - 8:25 p.m.
YWG
-
SAN
9h 55m
1 stop
Delta Logo
11:40 a.m. - 11:34 p.m.
SAN
-
YWG
9h 54m
1 stop
C$ 481Delta
Mon, 14 Sep - Wed, 23 Sep
WestJet Logo
7:00 a.m. - 2:10 p.m.
YWG
-
SAN
9h 10m
2 stops
WestJet Logo
3:30 p.m. - 12:55 a.m.
SAN
-
YWG
7h 25m
1 stop
C$ 488WestJet
Booking Insights

KAYAK's insights & trends for Winnipeg to San Diego flights

Get data-powered insights and trends into flights from Winnipeg to San Diego to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Winnipeg to San Diego?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Winnipeg to San Diego departing in October.

Flight prices are below average for this route right now.

Flights to San Diego from Winnipeg usually cost between C$ 526 and C$ 781 in October.
The lowest price found in the past 5 days was C$ 403 on WestJet (9 Oct–13 Oct).

What is the cheapest month to fly from Winnipeg to San Diego?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Winnipeg to San Diego, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Winnipeg to San Diego is March, where tickets cost C$ 455 (return) on average. On the other hand, the most expensive months are February and July, where the average cost of round-trip tickets is C$ 802 and C$ 687 respectively.

Good to know

Low season

April

Cheapest flight

C$ 258
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly (16% more expensive on average)
Flight from Winnipeg to San Diego

When to book flights from Winnipeg to San Diego

Are your dates flexible? Find out the best times to travel from Winnipeg to San Diego based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Winnipeg to San Diego

  • What is the cheapest flight from Winnipeg to San Diego?

    In the last 5 days, the lowest price for a flight from Winnipeg to San Diego was C$ 258 for a one-way ticket and C$ 403 for a round-trip.

  • Which aircraft models fly most regularly from Winnipeg to San Diego?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Winnipeg to San Diego?

    SkyTeam, and Star Alliance are the airline alliances operating flights between Winnipeg and San Diego, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Winnipeg to San Diego, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Winnipeg to San Diego are Delta and United Airlines. With an average price for the route of C$ 625 and an overall rating of 7.8, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of C$ 577 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Winnipeg to San Diego?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Winnipeg to San Diego.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Winnipeg to San Diego?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Diego from Winnipeg is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Winnipeg to San Diego?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to San Diego with an airline and back to Winnipeg with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Winnipeg to San Diego?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to San Diego from Winnipeg up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines flying from Winnipeg to San Diego

 
See real verified KAYAK customer reviews for airlines flying from Winnipeg to San Diego. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Winnipeg to San Diego? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
DeltaOverall score based on 8484 reviews
7.2Food
7.8Comfort
7.8Entertainment
8.5Crew
8.1Boarding
Airline reviews

Crew was real good, flight was smooth and came in early.

10.0 ExcellentAnonymous, Jun 2026
DTW - SAN
Read more Delta reviews

Crew was real good, flight was smooth and came in early.

Gate agent rushed to fill hot jetway with crowd so it took over 12 minutes to go from gate to plane. Just like a discount airline Pooly prepared cabin and third time that claim of rough air prevented any cabin service. Friends on a Southwest flight at similar time had service.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

Rough day of travel all the way around. Wrong info given to us multiple times and mistakes in their booking making our trip 10 hours longer than planned. I’m bummed because I fly Delta all the time and love them. Mistakes happen. Just bummed that this was a rare trip our whole family was traveling together.

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

Everything was very good other than I had selected a specific seat when I booked the flight and they changed it once I checked-in the day before my flight. I was still in first class but lost my aisle seat for a window seat. Being tall, the aisle offers more comfort so I always select an aisle seat.

Flight diverted in SD. Later take off in Seattle by 1.3hrs

Was a great smooth flight from Detroit to San Diego.

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

They made us check our bag…. Even though there was plenty of space up top… and then proceeded to shatter by brand new luggage 😞

We boarded the plane and were about to take off when we were notified that the tires had to be checked. Upon inspection, they were found to need replacement, so the entire plane had to be deboarded. After we exited the plane, United staff forced us to stay in the gate area by posting "Do Not Exit" signs on the doors connecting the gate area to the terminal. Many of us had already rebooked our flights and had no checked bags, but they told us we could not leave. This seemed inappropriate to hold people under false pretenses. When the agent told us we could leave, I asked them to please take down the "Do Not Exit" signs, as they were misleading. The agent refused, and I told them that it didn't feel right to hold people like that.

UA594 was delayed multiple times. I ended up getting picked up so I can make it in time for work 6AM on Monday, 7/6/2026

Friendly crew, but we were delayed for more than an hour and had to change planes due to maintenance issues.

Flight attendants had a little attitude. Food tastes no good.

Horrific. They missed my connecting flight to San Diego. I didn’t get there until Monday at 9am when I had a mandatory court settlement conference scheduled at 6am since we had parties on the east coast. This caused many issues. All because United apparently forgot to hold the doors open until my flight landed that only had a 10 minute delay. This was the last flight to Southern California. So I couldn’t even rent a car to finish the trip. United cannot be trusted when traveling on specific days and times since weather didn’t have anything to do with the delays.

Was a pain having to leave the plane and reboard but glad the plane was fixed

Connecting flights were poor,especially in Naples.our Lufthansa air bus was a joke.way too small for that long of a flight.no room at all.couldn’t even get out of the seats to move around or go to the bathrooms.we thought we were getting an actual air bus,double decker.i will never fly that long in a plane like that again.kind of misleading to call it an air bus.we actually had more room on our buses that we used.

For a 22 minute flight all you expect is for it to be safe and comfortable

Lost connnection had to stayON in Chicago Was a mess

Booked economy through United - air canada treated it as standby and was almost refused boarding.

My flight was cancelled due to weather but Westjet got me on a new flight in a timely and efficient manor.

No internet, not even westjet connect makes for a boring flight

Our first flight from LAX to Winnipeg was changed but you never informed us at all. It went from a nonstop flight to a stay at Calgary. This impacted our trip negatively as we arrived much later than we planned to. Our returning flight was horrible. The flight was delayed 6 hours!! And we were NOT going to wait that long. The only way we got on our original flight was running there. However all of our suitcases were now coming on the delayed flight. It was the worst experience we ever had flying. I want my money back.

Lots of overhead storage and a good crew and service.

On time. Friendly and efficient staff at check in and flight crew.

Very good over all , would have been nice to have entertainment on the flight

It was an awesome experience flying with Westjet. This was my first domestic flight experience in Canada.

Flight left on time. In flight entertainment options were good, but needed own device. Crew were polite.

The flight itself was fine, but two of the ladies at the gate were extremely rude to a few of us in line. Their customer service really needs some help. I’ve always had good experiences with WestJet until these two ladies. They had the worst attitudes and really left a bad taste in my mouth after a good trip

Smooth process, on time. Everything ran perfectly. It would be nice to have in flight entertainment and better food choices but these were short flights so not a big deal

Nice crew - very small plane and uncomfortable, with no entertainment options…

We were given an upgrade which provided more seat room and a meal. However seat designated overhead locker space was used by others.Boarding was delayed with part or the delay due to staff assisting diaablef individuals aboard. Personal observation would suggest that 3 individuals rorted the system. They used wheel chair access to the plane, boarding with family ahead of al other passengers, but required no assistance until boarding occurred. On departure 3 “disabled” individuals were seen walking freely near the baggage carousel. One person even assisted with a luggage trolley! The rorting is most likely widespread and not airline specific

Not good with Kayak … There is no customer service number to call ?? We have stuck at Toronto airport but air Canada don’t help because we bought tickets thru Kayak .. Kayak should have customer service number listed for help .. Very bad .. we will think twice to buy the tickets thru Kayak next time.. Ahluwalia

We paid $110 for more leg room. My traveling companion’s knees were right up against the seat in front. Where was more leg room. We feel ripped off. Food,,,there wasn’t any not even a bag of pretzels. As a result, there was very little service.

A 6 hour flt and only offered water twice the entire flight. A small bag of flavored pretzels was offered as well w/ the first round of beverages. The landing was ‘hot’ but I arrived safely. The plane was nice and new and the seats were roomie. I’m use to warmer more generous hospitality but all and all I’d fly with them again but I’d bring more water and snacks.

Headphones for the movies have too much bass and can't be adjusted. Almost impossible to hear. Great movie selections but can't really watch them because you can't hear them. Also the system is very slow.

No food for a 6 hours flight! Plus very expensive to buy ! Sit uncomfortable! Awful!!!

Air Canada didn't properly check the maintenance status of the plane prior to boarding it's passengers on to the plane. A final check before liftoff and we had to switch planes because of mechanical flaps issue.

The entertainment system is very slow. Scrolling through selections is slow.

The food and service were great! The flight was on time and comfortable.

Everything you need to know for your flight from Winnipeg to San Diego

Information on your arrival and departure airports