YWG - SJO

C$ 401 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 7/5. 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$ 775
Typical prices: C$ 1,474-C$ 1,192
Air Canada
Tue 2/6Fri 5/6
YWG - SJO • 2 stops
Cheapest one-way flights
C$ 340
Multiple Airlines
Thu 7/5
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$ 675 (round-trip)
Shortest trip • 9h 25m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 28% 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

Tue, 2 Jun - Fri, 5 Jun
Air Canada Logo
1:25 p.m. - 8:35 p.m.
YWG
-
SJO
32h 10m
2 stops
Air Canada Logo
7:10 a.m. - 11:08 a.m.
SJO
-
YWG
26h 58m
1 stop
C$ 775Air Canada
Tue, 7 Apr - Thu, 16 Apr
Multiple Airlines Logo
9:00 a.m. - 11:40 p.m.
YWG
-
SJO
15h 40m
2 stops
Multiple Airlines Logo
12:38 p.m. - 3:30 p.m.
SJO
-
YWG
25h 52m
2 stops
C$ 776Multiple Airlines
Tue, 2 Jun - Fri, 5 Jun
Air Canada Logo
1:25 p.m. - 8:35 p.m.
YWG
-
SJO
32h 10m
2 stops
Air Canada Logo
7:10 a.m. - 10:09 a.m.
SJO
-
YWG
25h 59m
2 stops
C$ 781Air Canada
Tue, 2 Jun - Fri, 5 Jun
Air Canada Logo
5:10 a.m. - 10:00 p.m.
YWG
-
SJO
17h 50m
1 stop
Air Canada Logo
7:10 a.m. - 11:08 a.m.
SJO
-
YWG
26h 58m
1 stop
C$ 782Air Canada
Sat, 25 Apr - Sat, 2 May
United Airlines Logo
2:00 p.m. - 12:21 p.m.
YWG
-
SJO
23h 21m
2 stops
United Airlines Logo
6:00 a.m. - 8:57 p.m.
SJO
-
YWG
37h 57m
2 stops
C$ 788United Airlines
Tue, 7 Apr - Thu, 16 Apr
Multiple Airlines Logo
9:00 a.m. - 11:40 p.m.
YWG
-
SJO
15h 40m
2 stops
Multiple Airlines Logo
12:38 p.m. - 3:30 p.m.
SJO
-
YWG
25h 52m
2 stops
C$ 801Multiple Airlines
Tue, 2 Jun - Thu, 4 Jun
United Airlines Logo
7:00 a.m. - 10:11 a.m.
YWG
-
SJO
28h 11m
2 stops
United Airlines Logo
12:30 a.m. - 8:57 p.m.
SJO
-
YWG
19h 27m
2 stops
C$ 840United Airlines
Mon, 11 May - Mon, 18 May
United Airlines Logo
8:45 a.m. - 12:21 p.m.
YWG
-
SJO
28h 36m
2 stops
United Airlines Logo
7:55 a.m. - 11:52 a.m.
SJO
-
YWG
26h 57m
2 stops
C$ 842United Airlines
Tue, 2 Jun - Fri, 5 Jun
United Airlines Logo
7:00 a.m. - 10:11 a.m.
YWG
-
SJO
28h 11m
2 stops
United Airlines Logo
7:55 a.m. - 11:52 a.m.
SJO
-
YWG
26h 57m
2 stops
C$ 844United Airlines
Fri, 8 May - Sun, 17 May
United Airlines Logo
2:00 p.m. - 5:30 a.m.
YWG
-
SJO
16h 30m
2 stops
United Airlines Logo
6:00 a.m. - 11:52 a.m.
SJO
-
YWG
52h 52m
2 stops
C$ 846United 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 June.

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$ 801 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is C$ 1,414 and C$ 1,356 respectively.

Good to know

Low seasonOctober
Cheapest flightC$ 340
Best time to beat the crowds (17% less expensive on average)
Most popular time to fly (22% 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$ 340 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$ 811 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$ 1,429 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 9499 reviews
6.6Food
7.1Entertainment
7.7Boarding
8.1Crew
7.3Comfort
Airline reviews

Flight delayed. Connecting to night flight was stressful but made it. Jusr in time. Ran.88Flight was fine.

4.0 OkayJack, Mar 2026
YYJ - YVR
Read more United Airlines reviews

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.

Given I (and I’m assuming most people) have both carry in and a personal item included in their fare, I find it very unfair that on neither of my flights I was able to use the overhead for my small backpack because they were completely rammed with luggage, people personal items, jackets, hats and other items. So the only item I brought in had to be stuffed under my seat while they had their leg room and sat comfortable with all of their items in the overhead. This has to stop because I was uncomfortable on both flights when I only had one smaller item that could not be checked due to its contents (medication etc). Plenty of people could have checked theirs but chose not to and then took up the space allotment for 2 people.

Flight attendants had a little attitude. Food tastes no good.

From pre boarding to flight attendant, crew and baggage handler, excellent. Didn’t lost my luggage like West jet.

Very poor. The flight was delayed from Toronto because some forget to do there job . I got to my connecting gate in San Francisco 10 minutes before the departure.but this didn’t let me board even though the flight was still there for an other 30 minutes. The the gentleman at the unite airline desk told me that they usually wait for passengers but air Canada called and told them not to we I been rerouted to Manila instead of Hong Kong . In San Francisco they mad me check in my carryon bag . I was told the it will directly go yo ho chi minn cuyt but I was told that by the Vietnams airline desk that’s not there I’m 10 hours behind my scheduled flight and looks like I I’m going without baggage. I don’t have a chance of catching ..

It was great. There were some issues prior to takeoff. The weather was poor so we had to go through deicing, and we were delayed a bit by the pilots' concern about one of the engines, but that's aviation. The pilots handled everything with aplomb, and kept us apprised

Reliable, nice crew, I fly often on that flight and I like it all.

l really enjoy very much the flight was very pleasant

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

It was great to have a vegetarian meal option, but departure was delayed because they had oversold the flight. Air Canada, you’re in charge of how many tickets are sold: don’t oversell!

Very disappointed with premier lounge. Food selection very poor, both coffee machines out of order. For the price you charge for an upgrade, the seats don’t fully recline, movie selection is old. Not very good value. Asian airlines are light years ahead at a more affordable price.

Boarded late then sat on the Tarmac for 90 minutes for no reason

The seat design in the premium economy section leaves virtually no room under the seat to store a bag or purse. Other than that, it was a great flight. Arrived early.

Delayed by 5+ hours and they give a voucher for only $20 CAD which isn’t even redeemable at any place with edible food. Then took almost an hour to clean craft after it landed. And nonsensical boarding delayed even further. We didn’t leave until 1:30am….

The flight was delayed, but not for weather. We landed over 3hrs later than planned.

The stag were helpful, kind and liked the passengers. The plane was pristinely clean! Great flight!

Crowded and tight fit on Rouge. Entertainment requires your own mobile device. Small bag of pretzels is only food for 3.5 hour flight.

Other than flights being cancelled and 3.5 hours late causing missed connections it was ok.

Flight late with no explanation why so late boarding. More than made up the time in flight. Woman in seat behind me would not allow me to recline my seat so could not sleep. Slow to clean up after meal so has to leave my tray down. Flight attendants average at best. Premium economy experience was poor. It was a special trip for us, a 70th birthday. We could only book seats that were apart and no efforts could be made to get us together. Just poor all around

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

Information on your arrival and departure airports