YWG - SJO

C$ 409 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 5/12. 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
Travellers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
C$ 775
Air Canada
Mon 26/10Fri 30/10
YWG - SJO • 1 stop
Cheapest one-way flights
C$ 409
Air Canada
Sat 5/12
YWG - SJO • 2 stops
Top airlines
Cheapest • from C$ 775 (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$ 1,364 (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
12:45 p.m. - 10:30 p.m.
YWG
-
SJO
10h 45m
1 stop
Air Canada Logo
7:45 a.m. - 6:25 p.m.
SJO
-
YWG
33h 40m
2 stops
C$ 775Air 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$ 778Air Canada
Mon, 26 Oct - Fri, 30 Oct
Air Canada Logo
6:55 p.m. - 10:50 p.m.
YWG
-
SJO
28h 55m
2 stops
Air Canada Logo
7:45 a.m. - 6:25 p.m.
SJO
-
YWG
33h 40m
2 stops
C$ 779Air Canada
Wed, 9 Dec - Sun, 24 Jan
Air Canada Logo
6:00 a.m. - 10:05 p.m.
YWG
-
SJO
16h 05m
2 stops
Air Canada Logo
8:35 a.m. - 10:16 a.m.
SJO
-
YWG
25h 41m
2 stops
C$ 823Air Canada
Mon, 26 Oct - Fri, 30 Oct
Air Canada Logo
12:45 p.m. - 10:30 p.m.
YWG
-
SJO
10h 45m
1 stop
Air Canada Logo
7:45 a.m. - 6:25 p.m.
SJO
-
YWG
33h 40m
2 stops
C$ 827Air Canada
Mon, 26 Oct - Fri, 30 Oct
Air Canada Logo
6:55 p.m. - 10:50 p.m.
YWG
-
SJO
28h 55m
2 stops
Air Canada Logo
7:45 a.m. - 6:25 p.m.
SJO
-
YWG
33h 40m
2 stops
C$ 831Air Canada
Sat, 7 Nov - Mon, 16 Nov
Air Canada Logo
6:55 p.m. - 10:30 p.m.
YWG
-
SJO
27h 35m
1 stop
Air Canada Logo
9:20 a.m. - 4:38 p.m.
SJO
-
YWG
31h 18m
1 stop
C$ 834Air Canada
Sat, 7 Nov - Mon, 16 Nov
Air Canada Logo
6:00 a.m. - 10:30 p.m.
YWG
-
SJO
40h 30m
2 stops
Air Canada Logo
9:20 a.m. - 6:25 p.m.
SJO
-
YWG
33h 05m
2 stops
C$ 837Air Canada
Sun, 8 Nov - Tue, 17 Nov
Air Canada Logo
6:55 p.m. - 10:30 p.m.
YWG
-
SJO
27h 35m
1 stop
Air Canada Logo
8:45 a.m. - 9:14 p.m.
SJO
-
YWG
12h 29m
1 stop
C$ 841Air Canada
Sun, 8 Nov - Tue, 17 Nov
Air Canada Logo
6:00 a.m. - 10:30 p.m.
YWG
-
SJO
40h 30m
2 stops
Air Canada Logo
8:45 a.m. - 6:25 p.m.
SJO
-
YWG
33h 40m
2 stops
C$ 844Air 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 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$ 1,667 and C$ 1,412 respectively.

Good to know

Low seasonMay
Cheapest flightC$ 409
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$ 409 for a one-way ticket and C$ 775 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$ 856 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$ 1,317 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 9896 reviews
7.3Comfort
7.7Boarding
7.1Entertainment
8.1Crew
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.

My experience on this United Airlines flight was highly uncomfortable, primarily due to two issues: Cabin Temperature: The temperature on the Boeing 737 MAX 8 was unacceptably high, feeling consistently around 80 degrees throughout the flight. This made sleeping impossible and significantly detracted from the experience. Seating Arrangement: Being stuck in a middle seat for a six-and-a-half-hour overnight flight compounded the discomfort. Moving forward, I will always purchase a seat assignment to avoid this situation.

I had very little time to change planes originally in Denver after my flight from Omaha. I had an hour and a half layover in Denver originally and my flight leaving Omaha was delayed an hour because they had to change a tire, which I can understand. When I reached Denver my other flight was late, fortunately, but I still had only 10 minutes to run about a mile through the airport to get to my flight. Again, fortunately, I am a healthy 71-year-old and was able to accomplish this feat. However, the stress was more than necessary to bear.

Flight was delayed twice which made our arrival extremely late (actually into next day). Not an easy travel. But when we requested assistance for boarding we were really impressed with how they helped us! Strongly praise their assistance.

every single person involved showed their joy, working in the airline industry - it created a very pleasant atmosphere for everyone

For boarding, after family with youngsters, you should have 65 and over. Whatever rules, enforce them. It’s frustrating for those who respect them to see aggressive people rush to the gate out of turn…

A snack would have been nice instead of having to buy food.

The plane was new. Should give more options on food.

No food other than a tiny snack. The flight is too long for not having a more substantial food option, other than buying the overprices and mostly non-plant-based options from the menu.

It was a refreshing experience from the past few times I have travelled with Air Canada.

rerouted on red eye. arrived 9 hours late with no luggage. still missing after 3 days. up to 45 day to deal with it. SHAME

The crew is super friendly and helpful , boarding was quick and easy , the prices are too high for a an airline that doesn’t provide complementary meals or snacks for long flights

The flight crew was nice and courteous. The food was terrible. There are no in-flight entertainment services, the plane is outdated and dilapidated, and the flight is delayed. Both from Newark and Montreal. Too bad.

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

Information on your arrival and departure airports