YWG - SJO

C$ 752 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 24/6. 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$ 752
Typical prices: C$ 1,475-C$ 684
Air Canada
Tue 22/9Sat 26/9
YWG - SJO • 1 stop
Cheapest one-way flights
C$ 449
United Airlines
Wed 24/6
YWG - SJO • 2 stops
Top airlines
Cheapest • from C$ 752 (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$ 673 (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, 22 Sep - Sat, 26 Sep
Air Canada Logo
2:05 p.m. - 10:00 p.m.
YWG
-
SJO
8h 55m
1 stop
Air Canada Logo
7:15 a.m. - 11:12 a.m.
SJO
-
YWG
26h 57m
2 stops
C$ 752Air Canada
Sun, 8 Nov - Tue, 17 Nov
Air Canada Logo
7:30 a.m. - 10:05 p.m.
YWG
-
SJO
14h 35m
1 stop
Air Canada Logo
8:35 a.m. - 10:39 p.m.
SJO
-
YWG
14h 04m
1 stop
C$ 781Air Canada
Sat, 7 Nov - Mon, 16 Nov
Air Canada Logo
7:20 p.m. - 11:15 p.m.
YWG
-
SJO
27h 55m
2 stops
Air Canada Logo
8:35 a.m. - 6:29 p.m.
SJO
-
YWG
9h 54m
1 stop
C$ 784Air Canada
Sat, 7 Nov - Mon, 16 Nov
Air Canada Logo
7:20 p.m. - 11:15 p.m.
YWG
-
SJO
27h 55m
2 stops
Air Canada Logo
8:35 a.m. - 10:16 a.m.
SJO
-
YWG
25h 41m
2 stops
C$ 788Air Canada
Tue, 22 Sep - Sat, 26 Sep
Air Canada Logo
12:20 p.m. - 10:00 p.m.
YWG
-
SJO
10h 40m
1 stop
Air Canada Logo
7:15 a.m. - 9:59 a.m.
SJO
-
YWG
25h 44m
1 stop
C$ 812Air Canada
Tue, 22 Sep - Sat, 26 Sep
Air Canada Logo
12:20 p.m. - 10:00 p.m.
YWG
-
SJO
10h 40m
1 stop
Air Canada Logo
7:15 a.m. - 9:14 p.m.
SJO
-
YWG
12h 59m
1 stop
C$ 813Air Canada
Tue, 22 Sep - Sat, 26 Sep
Air Canada Logo
2:05 p.m. - 10:00 p.m.
YWG
-
SJO
8h 55m
1 stop
Air Canada Logo
7:15 a.m. - 11:12 a.m.
SJO
-
YWG
26h 57m
2 stops
C$ 824Air Canada
Sun, 8 Nov - Tue, 17 Nov
Air Canada Logo
7:30 a.m. - 10:05 p.m.
YWG
-
SJO
14h 35m
1 stop
Air Canada Logo
8:35 a.m. - 10:39 p.m.
SJO
-
YWG
14h 04m
1 stop
C$ 854Air 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. - 10:39 p.m.
SJO
-
YWG
14h 04m
1 stop
C$ 856Air Canada
Sat, 7 Nov - Mon, 16 Nov
Air Canada Logo
7:20 p.m. - 10:05 p.m.
YWG
-
SJO
26h 45m
1 stop
Air Canada Logo
8:35 a.m. - 10:39 p.m.
SJO
-
YWG
14h 04m
1 stop
C$ 857Air 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 September.

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$ 1,312 and C$ 1,283 respectively.

Good to know

Low seasonApril
Cheapest flightC$ 449
Best time to beat the crowds (27% less expensive on average)
Most popular time to fly (5% 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$ 449 for a one-way ticket and C$ 752 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$ 766 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$ 1,283 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 9751 reviews
8.1Crew
7.1Entertainment
7.3Comfort
7.7Boarding
6.6Food
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.

Delays. Poor support booking a hotel after a diverted flight.

The TV screen at my seat was not functioning for the entire duration of the flight. I informed a flight attendant about the issue, and I was told that I would receive a voucher as compensation. However, I never received this voucher afterward. I therefore kindly request to still receive the voucher that was promised to me.

The staff were helpful with good relationships at all levels.- check in,in flight. BUT 1. The food provided was OK but inadequate supply. 2.in selecting my seat during the preboarding check in,I requested Change of seat which I did BUT without advice was charge $$ for this change!!

Flight crew was great, and even the crew for checking bags! I had a question for a friend of mine flying tomorrow and the man I talked to was awesome and answered my questions and looked up things for me when he didn’t have to! I was able to give her current & accurate info for her flight and she was so appreciative too!!

The Air Canada AC1 flight from Toronto to Tokyo on May 16 was great overall. Service, crew, food and entertainment were all excellent and everything ran smoothly. We had emergency exit seats so legroom was amazing, but the seats themselves weren’t very comfortable and the plane feels like it could use an upgrade for a long-haul flight. Aside from that, everything else was perfect.

Air traffic delay meant boarding started, then plane was evacuated and passengers sent back to the terminal for 1 hour. Very little information shared.

Never flown with Air Canada before, but it's now a top choice! Loved it!

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.

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

Information on your arrival and departure airports