YWG - SJO

C$ 308 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 27/10. 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

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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Flights 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

Thu, 23 Oct - Wed, 12 Nov
United Airlines Logo
4:25 p.m. - 12:26 p.m.YWG-SJO
45h 01m2 stops
United Airlines Logo
8:45 a.m. - 11:57 a.m.SJO-YWG
27h 12m2 stops
C$ 692United Airlines
Find Deal
Sat, 30 Aug - Wed, 3 Sep
 Logo
9:10 a.m. - 10:32 a.m.YWG-SJO
26h 22m1 stop
 Logo
12:18 p.m. - 4:22 p.m.SJO-YWG
27h 04m2 stops
C$ 700
Find Deal
Mon, 13 Oct - Fri, 17 Oct
 Logo
5:10 p.m. - 9:20 a.m.YWG-SJO
17h 10m2 stops
 Logo
1:41 p.m. - 6:32 p.m.SJO-YWG
27h 51m1 stop
C$ 711
Find Deal
Sun, 12 Oct - Sun, 19 Oct
United Airlines Logo
4:25 p.m. - 7:37 p.m.YWG-SJO
28h 12m2 stops
United Airlines Logo
7:55 a.m. - 10:33 p.m.SJO-YWG
37h 38m2 stops
C$ 767United Airlines
Find Deal
Sat, 11 Oct - Sun, 19 Oct
United Airlines Logo
4:25 p.m. - 12:26 p.m.YWG-SJO
21h 01m2 stops
United Airlines Logo
7:55 a.m. - 3:31 p.m.SJO-YWG
30h 36m2 stops
C$ 792United Airlines
Find Deal
Sat, 16 Aug - Sat, 23 Aug
 Logo
12:30 p.m. - 11:12 a.m.YWG-SJO
23h 42m3 stops
 Logo
12:18 p.m. - 7:24 p.m.SJO-YWG
30h 06m3 stops
C$ 795
Find Deal
Fri, 28 Nov - Tue, 2 Dec
Air Canada Logo
7:05 p.m. - 11:15 p.m.YWG-SJO
28h 10m2 stops
Air Canada Logo
8:35 a.m. - 9:44 p.m.SJO-YWG
13h 09m1 stop
C$ 991Air Canada
Find Deal
Thu, 23 Oct - Wed, 12 Nov
Air Canada Logo
5:00 a.m. - 10:55 p.m.YWG-SJO
18h 55m1 stop
Air Canada Logo
9:05 a.m. - 4:35 p.m.SJO-YWG
31h 30m1 stop
C$ 1,167Air Canada
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Wed, 30 Jul - Wed, 6 Aug
Avianca Logo
5:00 a.m. - 11:35 p.m.YWG-SJO
19h 35m2 stops
Avianca Logo
1:55 a.m. - 9:40 a.m.SJO-YWG
30h 45m2 stops
C$ 1,853Avianca
Find Deal
Wed, 30 Jul - Tue, 5 Aug
Avianca Logo
5:00 a.m. - 11:35 p.m.YWG-SJO
19h 35m2 stops
Avianca Logo
1:55 a.m. - 9:40 a.m.SJO-YWG
30h 45m2 stops
C$ 1,871Avianca
Find Deal
Useful Info

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$ 788 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is C$ 1,565 and C$ 1,481 respectively.

How far in advance should I book a flight from Winnipeg to San José?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Winnipeg to San José, you should book around 6 weeks before departure. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.


Good to know

Low seasonMay
High seasonJanuary
Cheapest flightC$ 308
Best time to beat the crowds (7% less expensive on average)
Most popular time to fly and prices are also 4% 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 3 days, the lowest price for a flight from Winnipeg to San José was C$ 226 for a one-way ticket and C$ 508 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?

    SkyTeam, and Star Alliance are the airline alliances operating flights between Winnipeg and San José, with Star Alliance being the most commonly used for this route.

  • 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$ 778 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$ 1,449 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 3 airlines serving 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 8861 reviews
8.1Crew
7.0Entertainment
7.7Boarding
6.6Food
7.3Comfort
Airline reviews

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

10.0 ExcellentAnonymous, Jul 2025YYZ - SFO
Read more United Airlines reviews

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

Very nice and clean plane. Transit time between flights was tight though

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

So far so good but food and entertainment are not available for this flight

Plane temperature was comfortable (not to hot) when boarding and waiting for takeoff.

Michael, our FA was very attentive, even finding me a chocolate brownie from economy class when the dessert selections were all dairy based. ( intolerant, not allergic so don’t usually need to order dairy free)

We tried to upgrade to economy premium but were told this was not possible as we had booked through United Airlines (and Air Canada was operating the flight). This seemed silly given there was ample space in economy premium. Additionally, we had to wait almost 1.5 hours upon arrival to taxi to the gate. Otherwise, the crew were very pleasant and passengers were friendly.

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

They screwed up so bad, I asked for a short check for my luggage since we had a 21 hour overnight layover in London at a hotel. They said I have to receive my luggage in London because it’s an overnight layover. Get to London, nope, my bags aren’t coming off they are staying in terminal 5 over night and going straight to Ibiza. So we had no luggage for a whole day and basically stuck with no clothes or washroom stuff. Finally get to Ibiza and my luggage is completely smashed and damaged and missing a wheel. Now I have to drag this 50 lbs luggage around Ibiza islands for 10 days. Wtf. So pissed off Air Canada is LITERALLY THE WORST AIRLINE IN THE WORLD

Took off on-time and staff was very nice. Got stuck on tarmac at ATL due to storms, but staff was still wonderful even though they were working and not getting paid.

At 6'2" the seat space was very cramped for economy. Otherwise good.

Staff was very courteous and kept things organized. We will definitely use Air Canada for further travel

Very good except paying twice for seat selection. Once when I booked and again when I checked in.

No issues other than paying twice for my seat selection.

Everything was great, clean plane and washrooms. Flight was on time, excellent boarding process

In a nutshell, my bag, the one I have to pay for, because now you can’t even bring a carry on, did not make it. I am still waiting for an update. The fact that not only were have to pay for it, but on top of that we are stuck without getting it, it’s ridiculous..

The plane was filthy!!!! There were empty food wrappers in the pockets and worst of all a wad of hair where someone had obviously brushed their hair, cleaned out the brush and left the wad of hair in the pocket. It was the most disgusting thing I’ve ever seen!! The seats are so crammed together with NO leg room. The AC vent controllers do not adjust. I will likely not book another AC flight from Florida to Montreal.

The app was great, service was wonderful, everything was quick and easy

Boarding was excessively slow. They do it by groups in a way that it doesn’t make sense. After business class , ppl that need assistance and any other priority group they should have ppl board from the back to the front. First rows 20+. Then 15+. Then 10, etc. having ppl sitting in the back board last makes no sense. The libe backame long as soon as ppl on rows 10 or so where told to board. The line went all the way up the ramp and tunnel for 25 mins.

The chicken that was served in business class was cold!

Flight to Bogotá delayed by 3 h Missed connection from Bogotá to Guayaquil. Avianca unable to bring us to Baltra on time Overall delay 36h. We missed boat departure from galagos. Overall 10 day trip needed to be cancelled. Avianca was completely un-professional.

I receive a service for what I pay, so it is fair.

A few years ago long flights 6 hours or so used to have video screens and they offered ear phones. The food cart used to come and drinks. Now absolutely nothing. Avianca is as bad as Spirit Airlines. Avianca will now be my last choice when booking my next flight.

Business class seats did not lie flat. There was only powdered milk for your coffee....in Business Class!! Food was good.

The seats were very uncomfortable. I would have upgrade or got different flight if I knew. I usually sleep in the plane but I couldn’t sleep at all. Very uncomfortable. Also no food or drink everything was to purchase, and that’s u usual for international flight.

There isn't much space in-between seats and even water needs to be paid for during the flight.

Flew with our two children. Paid $380 to check two bags (one was overweight). They then left the bags behind on Sunday, December 21st, with all our family’s clothes and family Christmas presents. When we arrived at our destination they told us the bags had not arrived, and they thought (but didn’t know) they were still in Boston, but that there’d be a flight the next day and the bags would arrive the next day. The next day we found out there was no flight, now we’re hoping we get our bags before we fly back out. Meanwhile, trying to get any engagement or accurate information is a waste of time. The folks at the call center are just gatekeepers, who can’t connect with any departments that actually do things to solve a problem. Getting information is made deliberately difficult. My biggest regret is that I’ve had a number of awful experiences with Avianca traveling between the US and Colombia, and still let myself get suckered into buying these tickets because the schedule was great. Never again.

COP 7,000 for a cup of mediocre coffee. I thought I was on Spirit Airlines for a minute. Otherwise the flight was fine. Nothing exceptional to report.

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