YWG - SJO

C$ 389 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 24/5. 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$ 795
Air Canada
Tue 27/10Tue 10/11
YWG - SJO • 1 stop
Cheapest one-way flights
C$ 385
Air Canada
Sun 24/5
YWG - SJO • 1 stop
Top airlines
Cheapest • from C$ 795 (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$ 669 (round-trip)
Shortest trip • 9h 25m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% 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

Tue, 27 Oct - Tue, 10 Nov
Air Canada Logo
8:15 a.m. - 10:15 p.m.
YWG
-
SJO
15h 00m
1 stop
Air Canada Logo
8:35 a.m. - 10:39 p.m.
SJO
-
YWG
14h 04m
1 stop
C$ 795Air Canada
Tue, 27 Oct - Tue, 10 Nov
Air Canada Logo
6:00 a.m. - 10:15 p.m.
YWG
-
SJO
17h 15m
2 stops
Air Canada Logo
8:35 a.m. - 8:59 p.m.
SJO
-
YWG
12h 24m
1 stop
C$ 796Air Canada
Tue, 27 Oct - Tue, 10 Nov
Air Canada Logo
6:00 a.m. - 10:15 p.m.
YWG
-
SJO
17h 15m
2 stops
Air Canada Logo
8:35 a.m. - 4:36 p.m.
SJO
-
YWG
32h 01m
2 stops
C$ 800Air Canada
Sat, 13 Jun - Fri, 26 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. - 11:15 a.m.
SJO
-
YWG
27h 05m
1 stop
C$ 814Air Canada
Mon, 15 Jun - Fri, 26 Jun
Air Canada Logo
2:00 p.m. - 10:00 p.m.
YWG
-
SJO
9h 00m
1 stop
Air Canada Logo
7:10 a.m. - 11:15 a.m.
SJO
-
YWG
27h 05m
1 stop
C$ 819Air Canada
Sat, 13 Jun - Fri, 26 Jun
Air Canada Logo
12:15 p.m. - 8:35 p.m.
YWG
-
SJO
33h 20m
2 stops
Air Canada Logo
7:10 a.m. - 11:15 a.m.
SJO
-
YWG
27h 05m
1 stop
C$ 825Air Canada
Sat, 7 Nov - Mon, 16 Nov
Air Canada Logo
6:00 a.m. - 10:05 p.m.
YWG
-
SJO
40h 05m
2 stops
Air Canada Logo
8:35 a.m. - 9:44 a.m.
SJO
-
YWG
25h 09m
1 stop
C$ 854Air Canada
Sat, 7 Nov - Mon, 16 Nov
Air Canada Logo
4:50 p.m. - 10:05 p.m.
YWG
-
SJO
29h 15m
1 stop
Air Canada Logo
8:35 a.m. - 1:44 p.m.
SJO
-
YWG
29h 09m
1 stop
C$ 855Air Canada
Sun, 8 Nov - Tue, 17 Nov
Air Canada Logo
5:15 a.m. - 10:05 p.m.
YWG
-
SJO
16h 50m
1 stop
Air Canada Logo
8:35 a.m. - 10:39 p.m.
SJO
-
YWG
14h 04m
1 stop
C$ 856Air Canada
Sat, 7 Nov - Mon, 16 Nov
Air Canada Logo
4:50 p.m. - 10:05 p.m.
YWG
-
SJO
29h 15m
1 stop
Air Canada Logo
8:35 a.m. - 9:44 a.m.
SJO
-
YWG
25h 09m
1 stop
C$ 858Air 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.

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

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 José departing in October.

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 October, where tickets cost C$ 0 (return) on average. On the other hand, the most expensive months are June and November, where the average cost of round-trip tickets is C$ 1,305 and C$ 1,276 respectively.

Good to know

Low seasonApril
Cheapest flightC$ 385
Best time to beat the crowds (27% less expensive on average)
Most popular time to fly (7% 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$ 385 for a one-way ticket and C$ 795 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$ 765 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$ 1,276 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 9737 reviews
6.6Food
8.1Crew
7.1Entertainment
7.7Boarding
7.3Comfort
Airline reviews

Seats very comfortable; service efficient and pleasant; flight was on-time; boarding organized.

10.0 ExcellentEirene, May 2026
YYZ - EWR
Read more United Airlines reviews

Seats very comfortable; service efficient and pleasant; flight was on-time; boarding organized.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

Good but airlines getting smaller. I didn't like the meal but the service was fine. Flight was fine and luggage arrived. So good.

They were fast and I like how they used to entertainment system to play video about the safety.

Flight delayed. Connecting to night flight was stressful but made it. Jusr in time. Ran.88Flight was fine.

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.

Our AC flight was canceled not once but twice on the same day to Quebec City at Toronto Pearson Airport. 2;30 AC and 9;40PM AC flight. After having our 2:35 flight canceled, we were bumped the second time because of large student groups visiting Quebec City. We were sent to Montreal on an 11:30 flight which landed close to 12:45AM. We were given a hotel room at the Marriot Hotel next to the airport. We had less than 4 hours sleep before we being taken to the airport for our 7AM flight to Quebec City. We didn't have much time to use our vouchers given for breakfast once we had cleared customs for the 2nd time since leaving Toronto Pearson Airport. We missed a full evening in Quebec City and lost our hotel room for the night. We were exhausted the next day and missed an excursion we had planned. My wife and I are both seniors in our seventies, and we weren't happy to be treated in this manner. Air Canada could have used a larger plane to accommodate us and the other ten or so people that were bumped from their flight to Quebec City in order to accommodate student groups. We will endeavor never to fly Air Canada again in future and we will not recommend flying with this airline to our friends and families.

As mentioned before the fact that my paid-for aisle seats had been changed to non-aisle seats is unacceptable. Happily one staff member at the boarding counter did correct it before the flights, otherwise I would have been forced to submit a formal complaint. If it happens again on return flights, I will put in a formal complaint.

Horrible crew, horrible seats configuration, ridiculous space in the toilets, Air Canada is no longer a option.

Disappointing experience with the cabin crews on this Air Canada flight. Some crew members came across as quite rude, and one bumped into my arm without even acknowledging it or apologising. A little courtesy and kindness would have gone a long way. Air turbulence is understandable. Human turbulence from the crew, less so.

Crew at gate and onboard were just very OK, not very friendly and honestly seemed bothered to be there. I will give a shout out to still selling headphones for those who forgot.

The long delay was the worst part of the flight.

Flight Boarded and departed on time. The Flight crew was very friendly and accommodating. The aircraft was clean and free from clutter and debris. I will be happy to recommend Air Canada to my friends and relatives for their flight needs. They were very attentive and responsive to our needs as Senior citizens.

We upgraded to business class. First time on Air Canada business class and they ran out of the better prawn dinner and we got chicken. Beds not as good as on Quantas

Another good flight experience with Air Canada. The business section did not feature the full length sleeping arrangement, but this was a shorter trip. The food was excellent. But the flight crew was truly top tier: friendly, cheerful, helpful at all the right times. Air Canada truly outshines all U.S. carriers.

Everything could be better, the worst is the crew, looks like they are not happy in the work. Air Canada is downhill for years, every flight looks worst. Hope they can fix the issues, by now, just flying AC in toutes with no other alternatives. Shame.

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

Information on your arrival and departure airports