YWG - SJO

C$ 386 Find Cheap Flights from Winnipeg to San José – 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 José departing on 17/9. 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

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$ 776
Air Canada
Mon 26/10Fri 30/10
YWG - SJO • 1 stop
Cheapest one-way flights
C$ 386
Air Canada
Thu 17/9
YWG - SJO • 1 stop
Top airlines
Cheapest • from C$ 776 (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$ 1,361 (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

Mon, 26 Oct - Fri, 30 Oct
Air Canada Logo
12:35 p.m. - 9:05 p.m.
YWG
-
SJO
9h 30m
1 stop
Air Canada Logo
7:35 a.m. - 9:44 a.m.
SJO
-
YWG
25h 09m
1 stop
C$ 776Air Canada
Mon, 26 Oct - Fri, 30 Oct
Air Canada Logo
7:30 a.m. - 9:05 p.m.
YWG
-
SJO
14h 35m
1 stop
Air Canada Logo
7:35 a.m. - 8:28 p.m.
SJO
-
YWG
35h 53m
2 stops
C$ 777Air Canada
Mon, 26 Oct - Fri, 30 Oct
Air Canada Logo
12:35 p.m. - 9:05 p.m.
YWG
-
SJO
9h 30m
1 stop
Air Canada Logo
7:35 a.m. - 9:44 a.m.
SJO
-
YWG
25h 09m
1 stop
C$ 781Air Canada
Mon, 26 Oct - Fri, 30 Oct
Air Canada Logo
7:30 a.m. - 9:05 p.m.
YWG
-
SJO
14h 35m
1 stop
Air Canada Logo
7:35 a.m. - 8:28 p.m.
SJO
-
YWG
35h 53m
2 stops
C$ 784Air Canada
Sun, 8 Nov - Tue, 17 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. - 8:59 p.m.
SJO
-
YWG
12h 24m
1 stop
C$ 805Air Canada
Sun, 8 Nov - Tue, 17 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. - 10:16 a.m.
SJO
-
YWG
25h 41m
2 stops
C$ 810Air Canada
Sun, 8 Nov - Tue, 17 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$ 811Air Canada
Fri, 3 Jul - Sun, 5 Jul
United Airlines Logo
8:45 a.m. - 10:11 a.m.
YWG
-
SJO
26h 26m
2 stops
United Airlines Logo
11:13 a.m. - 11:52 a.m.
SJO
-
YWG
23h 39m
2 stops
C$ 812United Airlines
Sun, 8 Nov - Tue, 17 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. - 10:16 a.m.
SJO
-
YWG
25h 41m
2 stops
C$ 815Air Canada
Sun, 8 Nov - Tue, 17 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. - 10:16 a.m.
SJO
-
YWG
25h 41m
2 stops
C$ 817Air 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 December and June, where the average cost of round-trip tickets is C$ 1,663 and C$ 1,408 respectively.

Good to know

Low seasonMay
Cheapest flightC$ 386
Best time to beat the crowds (43% less expensive on average)
Most popular time to fly and prices are also 5% lower 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 5 days, the lowest price for a flight from Winnipeg to San José was C$ 391 for a one-way ticket and C$ 776 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$ 854 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$ 1,313 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 9875 reviews
8.1Crew
7.3Comfort
7.1Entertainment
7.7Boarding
6.6Food
Airline reviews

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

2.0 MediocreGreg, Jun 2026
YYZ - ORD
Read more United Airlines reviews

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Boarding was smooth and efficient. The only food was some pretzels, but it was a short flight. Not much to order if you were hungry.

Crew were welcoming, accommodating and they worked hard to find places for all carry on.

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.

The meal options were ok but the actual food was terrible. On my return journey, they simply said that there was no vegetarian option and somehow struggled to give me dinner and did not give me any breakfast at all which in my opinion was terrible. Not having ANY vegetarian meal was surprising and never had such an experience in the recent years.

Every flight was canceled and they didn’t care much about their passengers

Smooth ride but I wish they have better food selections.

Flight got delayed But satisfied with the pricing of tickets

Aircraft is designed with all 3 washrooms at the back of the plane, meaning that when there is service underway, there are no washrooms available and it gets very crowded at the back of the plane.

I was through check-in right away and on the plane before I knew it perfect in every way

Multiple delays and gate changes resulting in arrival with a 5 hour delay.

Mutiple delays and changes of gate resulting in arrival 5 hours after intended.

Excellent flight crew. Very comfortable plane. Entertainment options on air Canada were great!

One crew member, Brandy was very helpful with recovering phone lost in customs. The plane was ancient and poorly maintained. Checked baggage did not arrive with flight. Almost missed flight because if insanely short layover time. Air Canada is worst flight I have ever booked with Kayak. Wanted to charge for headsets for on flight media.

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

Information on your arrival and departure airports