YWG - SJO

C$ 369 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 28/1. 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$ 657
Typical prices: C$ 1,001-C$ 1,623
Multiple Airlines
Mon 12/1Mon 19/1
YWG - SJO • 1 stop
Cheapest one-way flights
C$ 369
Multiple Airlines
Wed 28/1
YWG - SJO • 3 stops
When to book
2 weeks
in advance
Our data shows that travellers who book at least 2 weeks in advance save around 19% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
July
Cheapest • 28% price drop
January
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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, 12 Jan - Mon, 19 Jan
Multiple Airlines Logo
8:00 a.m. - 12:22 p.m.
YWG
-
SJO
28h 22m1 stop
Multiple Airlines Logo
1:30 p.m. - 12:42 a.m.
SJO
-
YWG
35h 12m2 stops
C$ 657Multiple Airlines
Thu, 22 Jan - Thu, 5 Feb
Multiple Airlines Logo
12:20 p.m. - 11:35 p.m.
YWG
-
SJO
11h 15m1 stop
Multiple Airlines Logo
1:30 p.m. - 3:30 p.m.
SJO
-
YWG
26h 00m2 stops
C$ 666Multiple Airlines
Tue, 3 Mar - Tue, 10 Mar
United Airlines Logo
2:20 p.m. - 6:16 p.m.
YWG
-
SJO
27h 56m2 stops
United Airlines Logo
1:05 p.m. - 11:57 a.m.
SJO
-
YWG
21h 52m1 stop
C$ 670United Airlines
Wed, 25 Feb - Tue, 3 Mar
Multiple Airlines Logo
8:05 p.m. - 11:35 p.m.
YWG
-
SJO
27h 30m1 stop
Multiple Airlines Logo
4:15 p.m. - 11:32 a.m.
SJO
-
YWG
19h 17m2 stops
C$ 720Multiple Airlines
Wed, 21 Jan - Wed, 4 Feb
Multiple Airlines Logo
7:30 a.m. - 11:37 a.m.
YWG
-
SJO
28h 07m3 stops
Multiple Airlines Logo
12:33 p.m. - 7:09 p.m.
SJO
-
YWG
30h 36m2 stops
C$ 749Multiple Airlines
Thu, 22 Jan - Thu, 5 Feb
Lufthansa Logo
2:20 p.m. - 1:15 p.m.
YWG
-
SJO
22h 55m2 stops
Lufthansa Logo
2:20 p.m. - 11:57 a.m.
SJO
-
YWG
21h 37m2 stops
C$ 753Lufthansa
Wed, 14 Jan - Wed, 21 Jan
Multiple Airlines Logo
7:30 a.m. - 11:37 a.m.
YWG
-
SJO
28h 07m3 stops
Multiple Airlines Logo
12:33 p.m. - 11:35 a.m.
SJO
-
YWG
23h 02m2 stops
C$ 754Multiple Airlines
Wed, 21 Jan - Wed, 4 Feb
Multiple Airlines Logo
7:30 a.m. - 11:37 a.m.
YWG
-
SJO
28h 07m3 stops
Multiple Airlines Logo
12:33 p.m. - 12:07 p.m.
SJO
-
YWG
47h 34m3 stops
C$ 760Multiple Airlines
Mon, 12 Jan - Wed, 11 Feb
United Airlines Logo
2:20 p.m. - 1:15 p.m.
YWG
-
SJO
22h 55m2 stops
United Airlines Logo
8:45 a.m. - 11:57 a.m.
SJO
-
YWG
27h 12m2 stops
C$ 763United Airlines
Wed, 25 Feb - Tue, 3 Mar
Multiple Airlines Logo
4:10 p.m. - 1:50 p.m.
YWG
-
SJO
21h 40m3 stops
Multiple Airlines Logo
7:22 a.m. - 6:05 p.m.
SJO
-
YWG
34h 43m3 stops
C$ 765Multiple Airlines
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 January.

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$ 815 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is C$ 1,525 and C$ 1,523 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 2 weeks before departure, which saves you about 19% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonOctober
Cheapest flightC$ 369
Best time to beat the crowds (20% less expensive on average)
Most popular time to fly (8% 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$ 369 for a one-way ticket and C$ 657 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$ 815 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$ 1,446 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 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 9095 reviews
7.7Boarding
7.1Entertainment
7.3Comfort
8.1Crew
6.6Food
Airline reviews

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

8.0 ExcellentAnonymous, Dec 2025
YEG - IAH
Read more United Airlines reviews

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

Quick and seamless boarding. No entertainment but fast Starlink wifi for this short trip and the staff was really friendly.

I dread trans-Pacific flights. They are very long. This was my first time on Universal, and it was my best crossing ever. The staff were professional, the hospitality was great, and the food was delicious. The entertainment system filled the long flight hours. I will seek out Universal flights from now onwards. 🙂

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.

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

We Left Calgary 1/2 hour late and that made for a tight connection in Denver. After arriving everything was done to help us make our connection. That was a great effort. Thank You United

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Overall, it was good. I was seating next to a wonderful lady and did not notice how time flew. Thanks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

The experience was great, the crew was very polite and hospitable. I will definitely make if my go to airlines.

My seat was covered in vomit and I will be reaching out to Air Canada

We were happy with the service and cost of checking a bag

I would like to review the next flight from Toronto to Fort Myers as it was a disaster!!

This flight with a lot empty place , and I have more room, feeling comfortable.

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

Flight was cancelled. Not enough agents to deal with the people in the line. We left and found our own way to Vancouver.

Flight was good, breakfast could be much better. We had come from a domestic flight on the same aircraft and the domestic flight was much better regarding service compared to this international flight.

Flight was great. Meal was really good. Boarding was terrible. Too many people in a small boarding lounge, zones not clearly marked.

3 hr delay at the gate while they were doing maintenance. Next time, do not board passengers while maintenance is being performed

Digital check in is very poor with air canada compaired to other airlines

We waited for one hour to deboard the plane after landing. That could be better

I handed in my suitcase in perfect condition at SAL Airport. And in MIA Airport I received it with one corner broken and the wheels bent.

I like the crew they're very friendly. I don't like. on five hour flight they not offered snacks. Any drink. Not even coffee

Not even water is offered on the flight. You cannot lean back on the seats and the seats are so narrow you can’t avoid rubbing elbows with the person next to you.

I had to go to the boarding counter for them to enter my return flight as it’s not with Avianca. There was a long queue as there were lots of people being called to the counter.

Horrible experience. Flight cancelled. Arrived at destination 12 hs later. No one gave us an answer or any information. Very very poor service. We won’t ever travel again with Avianca

Did not fly with Pakistan International Airlines. Have never flown with Pakistan International Airlines.

Usb plugs for charging your phone does not work in every flight. uncomfortable chairs even in higher categories.

Luggage lost and nowhere to be found, no response from either airline regarding my bag

The seats were uncomfortable and barely reclined at all. Very little leg room despite being business class. The crew was friendly and the food was good. Had to use my own phone for in-flight entertainment.

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

Information on your arrival and departure airports