YWG - SJO

C$ 347 Find Cheap Flights from Winnipeg to San José

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 José departing on 6/5. 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

KAYAK searches hundreds of travel sites at once for deals on flights to San José

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to San José, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to San José, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
C$ 760
Overall average: C$ 1,078
Air Canada
Sat 30/5Mon 8/6
YWG - SJO • 1 stop
Cheapest one-way flights
C$ 347
Multiple Airlines
Wed 6/5
YWG - SJO • 3 stops
Top airlines
Cheapest • from C$ 760 (round-trip)
Best reviews • 7.4 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 José. You’ll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg C$ 668 (round-trip)
Shortest trip • 9h 25m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 28% 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 José!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Winnipeg to San José (YWG-SJO)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to San José 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 José

Sat, 30 May - Mon, 8 Jun
Air Canada Logo
4:05 p.m. - 8:35 p.m.
YWG
-
SJO
29h 30m
1 stop
Air Canada Logo
7:15 a.m. - 10:09 a.m.
SJO
-
YWG
25h 54m
1 stop
C$ 760Air Canada
Sun, 31 May - Wed, 3 Jun
Air Canada Logo
8:00 a.m. - 8:35 p.m.
YWG
-
SJO
13h 35m
1 stop
Air Canada Logo
8:00 a.m. - 11:18 p.m.
SJO
-
YWG
14h 18m
1 stop
C$ 767Air Canada
Sun, 31 May - Wed, 3 Jun
Air Canada Logo
8:00 a.m. - 8:35 p.m.
YWG
-
SJO
13h 35m
1 stop
Air Canada Logo
8:00 a.m. - 11:08 a.m.
SJO
-
YWG
26h 08m
1 stop
C$ 768Air Canada
Sun, 31 May - Wed, 3 Jun
Air Canada Logo
8:00 a.m. - 8:35 p.m.
YWG
-
SJO
13h 35m
1 stop
Air Canada Logo
8:00 a.m. - 10:09 a.m.
SJO
-
YWG
25h 09m
2 stops
C$ 771Air Canada
Sun, 31 May - Wed, 3 Jun
Air Canada Logo
11:00 a.m. - 8:35 p.m.
YWG
-
SJO
10h 35m
1 stop
Air Canada Logo
7:10 a.m. - 10:09 a.m.
SJO
-
YWG
25h 59m
2 stops
C$ 772Air Canada
Sun, 31 May - Wed, 3 Jun
Air Canada Logo
1:25 p.m. - 10:00 p.m.
YWG
-
SJO
33h 35m
2 stops
Air Canada Logo
7:10 a.m. - 11:08 a.m.
SJO
-
YWG
26h 58m
1 stop
C$ 774Air Canada
Fri, 29 May - Fri, 5 Jun
Air Canada Logo
5:10 p.m. - 10:00 p.m.
YWG
-
SJO
29h 50m
1 stop
Air Canada Logo
7:10 a.m. - 10:09 a.m.
SJO
-
YWG
25h 59m
2 stops
C$ 778Air Canada
Sun, 31 May - Wed, 3 Jun
Air Canada Logo
1:25 p.m. - 10:00 p.m.
YWG
-
SJO
33h 35m
2 stops
Air Canada Logo
8:00 a.m. - 10:09 a.m.
SJO
-
YWG
25h 09m
2 stops
C$ 779Air Canada
Thu, 28 May - Mon, 8 Jun
Air Canada Logo
5:10 a.m. - 8:35 p.m.
YWG
-
SJO
40h 25m
2 stops
Air Canada Logo
7:15 a.m. - 11:08 a.m.
SJO
-
YWG
26h 53m
2 stops
C$ 782Air Canada
Sat, 30 May - Sun, 7 Jun
Air Canada Logo
4:05 p.m. - 8:35 p.m.
YWG
-
SJO
29h 30m
1 stop
Air Canada Logo
7:10 a.m. - 10:09 a.m.
SJO
-
YWG
25h 59m
2 stops
C$ 819Air Canada
Booking Insights

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Winnipeg to San José, 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 José is July, where tickets cost C$ 793 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is C$ 1,399 and C$ 1,342 respectively.

Good to know

Low seasonOctober
Cheapest flightC$ 347
Best time to beat the crowds (17% less expensive on average)
Most popular time to fly (22% more expensive on average)
Flight from Winnipeg to San José

When to book flights from Winnipeg to San José

Are your dates flexible? Find out the best times to travel from Winnipeg to San José 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 José

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

    In the last 3 days, the lowest price for a flight from Winnipeg to San José was C$ 347 for a one-way ticket and C$ 760 for a round-trip.

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

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

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

    Star Alliance is the only airline alliance operating flights between Winnipeg and San José.

  • Which is the best airline for flights from Winnipeg to San José, United Airlines or Air Canada?

    The two airlines most popular with KAYAK users for flights from Winnipeg to San José are United Airlines and Air Canada. With an average price for the route of C$ 802 and an overall rating of 7.4, United Airlines is the most popular choice. Air Canada is also a great choice for the route, with an average price of C$ 1,414 and an overall rating of 7.1.

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

    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 José.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San José 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 José?

    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 José 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 José?

    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 José 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 airlines flying from Winnipeg to San José

 
See real verified KAYAK customer reviews for airlines flying from Winnipeg to San José. 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 José? 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.
7.4
United AirlinesOverall score based on 9462 reviews
6.6Food
7.7Boarding
7.3Comfort
8.1Crew
7.1Entertainment
Airline reviews

Hopped on time for the flight only to get deplaned and delayed another 2.5 hours.

2.0 MediocreMary Ann, Mar 2026
YYZ - EWR
Read more United Airlines reviews

Hopped on time for the flight only to get deplaned and delayed another 2.5 hours.

Given I (and I’m assuming most people) have both carry in and a personal item included in their fare, I find it very unfair that on neither of my flights I was able to use the overhead for my small backpack because they were completely rammed with luggage, people personal items, jackets, hats and other items. So the only item I brought in had to be stuffed under my seat while they had their leg room and sat comfortable with all of their items in the overhead. This has to stop because I was uncomfortable on both flights when I only had one smaller item that could not be checked due to its contents (medication etc). Plenty of people could have checked theirs but chose not to and then took up the space allotment for 2 people.

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

From pre boarding to flight attendant, crew and baggage handler, excellent. Didn’t lost my luggage like West jet.

Very poor. The flight was delayed from Toronto because some forget to do there job . I got to my connecting gate in San Francisco 10 minutes before the departure.but this didn’t let me board even though the flight was still there for an other 30 minutes. The the gentleman at the unite airline desk told me that they usually wait for passengers but air Canada called and told them not to we I been rerouted to Manila instead of Hong Kong . In San Francisco they mad me check in my carryon bag . I was told the it will directly go yo ho chi minn cuyt but I was told that by the Vietnams airline desk that’s not there I’m 10 hours behind my scheduled flight and looks like I I’m going without baggage. I don’t have a chance of catching ..

It was great. There were some issues prior to takeoff. The weather was poor so we had to go through deicing, and we were delayed a bit by the pilots' concern about one of the engines, but that's aviation. The pilots handled everything with aplomb, and kept us apprised

Reliable, nice crew, I fly often on that flight and I like it all.

l really enjoy very much the flight was very pleasant

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

Quick and seamless boarding. No entertainment but fast Starlink wifi for this short trip and the staff was really friendly.

Crowded and tight fit on Rouge. Entertainment requires your own mobile device. Small bag of pretzels is only food for 3.5 hour flight.

Other than flights being cancelled and 3.5 hours late causing missed connections it was ok.

Flight late with no explanation why so late boarding. More than made up the time in flight. Woman in seat behind me would not allow me to recline my seat so could not sleep. Slow to clean up after meal so has to leave my tray down. Flight attendants average at best. Premium economy experience was poor. It was a special trip for us, a 70th birthday. We could only book seats that were apart and no efforts could be made to get us together. Just poor all around

Flight departed significantly late with no announcements being made. Woman behind me would not allow me to recline my seat so I was unable to comfortably sleep. Flight attendant not very responsive. Slow to pick up garbage after meal. Not a good experience at all. I felt like cattle rather than like a valued customer

My flight was delayed more than once, but Air Canada updated us regularly. Friends on other airlines had much worse experiences.

By modern air travel standards, our 15-hour flight to Delhi was very nice. Quiet-ish, straightforward, good service, okay seats, etc. All good.

Again, it was delayed and then our connecting aircraft was very cold.

My ticket did not exist when I got to the airport. I had to book another flight and was still charged by Kayak

Got denied my flight was told on Google that Air Canada was supposed to book me a flight back home because I never was able to go to my destination. They did not help me whatsoever. I had to book a whole new flight for that reason I would write this is zero

The plane was delayed an hour. Heard from other passengers that the Vancouver connection to SFO was never on-time.

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

Information on your arrival and departure airports