YWG - SJO

C$ 669 Find Cheap Flights from Winnipeg to San José

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to San José departing on 19/8. 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

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 Flight Deals 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.

Recent round-trip flight deals from Winnipeg to San José

KAYAK's recommended round-trip deals from the most popular airlines that fly from Winnipeg to San José.
Discover the best prices for you by selecting your travel dates on KAYAK.
United Airlines Logo
2:20 p.m. - 12:26 p.m.YWG-SJO
23h 06m2 stops
United Airlines Logo
7:55 a.m. - 1:09 p.m.SJO-YWG
28h 14m2 stops
C$ 669United Airlines
Find Deal
Tue, 19 Aug - Tue, 26 Aug
United Airlines Logo
7:00 a.m. - 10:11 a.m.YWG-SJO
28h 11m2 stops
United Airlines Logo
8:45 a.m. - 1:03 p.m.SJO-YWG
28h 18m2 stops
C$ 695United Airlines
Find Deal
Thu, 26 Jun - Tue, 11 Nov
United Airlines Logo
4:25 p.m. - 10:11 a.m.YWG-SJO
42h 46m2 stops
United Airlines Logo
5:30 a.m. - 3:31 p.m.SJO-YWG
33h 01m2 stops
C$ 745United Airlines
Find Deal
Tue, 17 Jun - Fri, 27 Jun
 Logo
6:30 a.m. - 10:37 a.m.YWG-SJO
29h 07m3 stops
 Logo
11:32 a.m. - 4:28 p.m.SJO-YWG
27h 56m2 stops
C$ 760
Find Deal
Tue, 17 Jun - Tue, 24 Jun
 Logo
6:30 a.m. - 10:27 a.m.YWG-SJO
28h 57m2 stops
 Logo
11:32 a.m. - 9:43 a.m.SJO-YWG
21h 11m2 stops
C$ 771
Find Deal
Tue, 27 May - Tue, 3 Jun
Air Canada Logo
2:50 p.m. - 10:50 p.m.YWG-SJO
9h 00m1 stop
Air Canada Logo
8:00 a.m. - 11:23 p.m.SJO-YWG
14h 23m1 stop
C$ 1,127Air Canada
Find Deal
Tue, 17 Jun - Fri, 27 Jun
Air Canada Logo
11:10 a.m. - 10:50 p.m.YWG-SJO
12h 40m2 stops
Air Canada Logo
8:00 a.m. - 9:40 a.m.SJO-YWG
24h 40m1 stop
C$ 1,182Air Canada
Find Deal
Tue, 17 Jun - Fri, 27 Jun
Avianca Logo
6:35 p.m. - 9:20 a.m.YWG-SJO
15h 45m2 stops
Avianca Logo
2:15 a.m. - 12:43 p.m.SJO-YWG
33h 28m2 stops
C$ 1,552Avianca
Find Deal
Sat, 18 Oct - Fri, 31 Oct
Avianca Logo
4:30 p.m. - 9:20 a.m.YWG-SJO
17h 50m2 stops
Avianca Logo
1:55 a.m. - 9:40 a.m.SJO-YWG
30h 45m2 stops
C$ 1,683Avianca
Find Deal
Wed, 28 May - Tue, 3 Jun
Delta Logo
9:00 a.m. - 11:59 a.m.YWG-SJO
27h 59m1 stop
Delta Logo
1:24 p.m. - 4:28 p.m.SJO-YWG
26h 04m1 stop
C$ 3,496Delta
Find Deal
Tue, 27 May - Tue, 3 Jun
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 August, where tickets cost C$ 822 (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$ 1,819 and C$ 1,606 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.


Good to know

Low seasonJune
High seasonJanuary
Cheapest flightC$ 669
Best time to beat the crowds but there is an average 27% increase in price.
Most popular time to fly and prices are also 9% 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$ 554 for a one-way ticket and C$ 483 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$ 814 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$ 1,493 and an overall rating of 7.0.

  • 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.

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 8696 reviews
7.7Boarding
8.1Crew
6.6Food
7.1Entertainment
7.3Comfort
Airline reviews

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

2.0 MediocreBrant, Apr 2025YHZ - EWR
Read more United Airlines reviews

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.

headphone jack didnt work for the first flight and not much variety

Plane 3 hours late. Missed connection. No help from gate staff. App horrible. Lost connection repeatedly. No service desk. Finally got help from young girl driving cart.

Not as good as expected Air Can needs to improve totally rated on internet as worst

The flight was delayed, it took longer than anticipated because of weather, and they broke my luggage.

As usual, terrible. Delayed flight, missed connection and wasted hours at the airport. The only reason I use this airline is because of limited options.

My flight got delayed 5 times and then got cancelled eventually, I had to get a hotel and uber and pay for food for an extra night without any plans. It was a horrible experience, instead of Air Canada, I was flying with United .

I had a nice flight with free wifi. So I was able to message family members and stream music during my flight, which made the trip go by fast. I also enjoyed flying on there Airbus A220. The plane looked very new and it also got up to speed fast down the runway and didn't need much runway to get airborne.

nothing exceptional and like other airlines food becoming smaller in size...

Lynda was rude and unhelpful. We asked for tea wiht a slice of lemon. She served us Coffee instead. When we spoke to her she made it seem as if we were lying. I asked if she would like to taste it and see - her reply was I don’t need to be rude. After this incident we were treated with subpar service for all beverages and food items after. We’re were purposely left out when they did garbage collection.

They lost my checked in luggage, why do I pay for my cargo not arriving at the same destination as me?

Overall good experience. The flight from Toronto to Denver does not have entertainment - movies to watch.

Not enough electronic outlets for charging in the Air Canada waiting to board area but the Most important thing….the plane was booked to only 40% capacity and my row of 2 other seats were empty. My row happened to be one of the few rows that did NOT have raising arm rests. The flight attendant made effort to seat me in a different row. I needed wheelchair assistance due to a cyst on my knee and struggled to move from seat to seat to get to the row. Those 2 empty seats tormented me the entire 15+ hour flight as I had to be upright the entire flight and was not able to elevate my knee. Lots of other passengers were laying down due to the arm rest being able to retract. It is a shame that he couldn’t be gracious and find a row that I could move to.

Crew was pleasant and efficient. The speaker system for instructions was hard to understand

There is not enough space between two chairs and raws.

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

Purchased a business class ticket and got a economy seat with center seat blocked they call it business. 3100usd ticket on a flight where economy costs 500usd The biggest scam insult have had on a regular airline. Avianca should be in the low cost category and kicked out of Star Alliance. I want the difference to be credited. Ets see what Avianca does. No reply so far. Avianca = low cost airline. Beware

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

Excellent flight and one of the smoothest landing I’ve ever experienced

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.

We were not aware carry-on bags cost extra until we arrived at the airport so, we were charged $240.00 for two small carry- on bags! There was a substantial fee for drinks and snacks. No wifi, or other entertainment was available. Waiting areas were crowded and uncomfortable.

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.

please see previous response; it covers the whole travel trajectory.

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