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Cheap flights from Winnipeg to San José from C$ 369

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 27/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJO
26 Aug — 2 Sep1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to San José

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to San José
Explore the most affordable flight options available from Winnipeg to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 27 July 2026.

Thu 3/94:10 p.m.
YWG
-
SJO
1 stop29h 10m
Air Canada
Fri 25/97:10 a.m.
SJO
-
YWG
2 stops11h 50m
Air Canada
Deal found 25/7C$ 713
Sun 13/98:45 a.m.
YWG
-
SJO
2 stops28h 36m
United Airlines
Fri 25/97:55 a.m.
SJO
-
YWG
2 stops27h 42m
United Airlines
Deal found 23/7C$ 721
Sat 31/106:55 p.m.
YWG
-
SJO
1 stop28h 35m
Air Canada
Sat 7/119:20 a.m.
SJO
-
YWG
1 stop31h 18m
Air Canada
Deal found 26/7C$ 738
Sat 31/102:40 p.m.
YWG
-
SJO
1 stop32h 50m
Air Canada
Sun 8/118:45 a.m.
SJO
-
YWG
1 stop12h 29m
Air Canada
Deal found 26/7C$ 745
Sat 12/98:45 a.m.
YWG
-
SJO
2 stops11h 52m
United Airlines
Fri 25/91:25 p.m.
SJO
-
YWG
2 stops22h 12m
United Airlines
Deal found 23/7C$ 761
Wed 11/1111:20 a.m.
YWG
-
SJO
1 stop11h 10m
Air Canada
Sun 15/118:45 a.m.
SJO
-
YWG
1 stop14h 59m
Air Canada
Deal found 24/7C$ 771
Sun 8/116:55 p.m.
YWG
-
SJO
1 stop27h 35m
Air Canada
Tue 17/118:45 a.m.
SJO
-
YWG
1 stop10h 24m
Air Canada
Deal found 27/7C$ 772
Wed 14/108:45 a.m.
YWG
-
SJO
2 stops28h 36m
United Airlines
Wed 21/101:25 p.m.
SJO
-
YWG
2 stops22h 12m
United Airlines
Deal found 25/7C$ 782

Find flight deals from Winnipeg to San José

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to San José (SJO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 27 July 2026.

Round-trip from

C$ 713

One-way from

C$ 369

Popular in

December

Cheapest in

May

Average price

C$ 1,489
Air Canada
  • Air Canada
  • 11/9-25/9
  • 2 total stops
  • 26h 27m total
  • Winnipeg to San José
Search Deals
Air Canada
  • Air Canada
  • 27/8
  • 1 total stop
  • 29h 10m total
  • Winnipeg to San José
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 148 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 57 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to San José that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 27 July 2026.
Use the filters below to find and compare flights from Winnipeg to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 13/9

8:45 a.m.-12:21 p.m.

2 stops28h 36m

San José Juan Santamaria Intl

Fri 25/9

7:55 a.m.-12:37 p.m.

2 stops27h 42m

C$ 721

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 14/9

7:00 a.m.-12:21 p.m.

2 stops30h 21m

San José Juan Santamaria Intl

Fri 25/9

1:25 p.m.-10:33 p.m.

2 stops32h 08m

C$ 721
Quickest round-trip

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 8/11

6:55 p.m.-10:30 p.m.

1 stop27h 35m

San José Juan Santamaria Intl

Tue 17/11

8:45 a.m.-7:09 p.m.

1 stop10h 24m

C$ 772

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 14/10

8:45 a.m.-12:21 p.m.

2 stops28h 36m

San José Juan Santamaria Intl

Wed 21/10

1:25 p.m.-12:37 p.m.

2 stops22h 12m

C$ 782

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 7/11

6:55 p.m.-11:50 p.m.

2 stops28h 55m

San José Juan Santamaria Intl

Mon 16/11

9:20 a.m.-10:00 a.m.

1 stop24h 40m

C$ 812

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 23/10

8:45 a.m.-12:21 p.m.

2 stops28h 36m

San José Juan Santamaria Intl

Sat 14/11

8:45 a.m.-12:23 p.m.

2 stops27h 38m

C$ 812

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 16/1

2:15 p.m.-8:39 p.m.

2 stops30h 24m

San José Juan Santamaria Intl

Sat 6/2

8:45 a.m.-11:39 a.m.

2 stops26h 54m

C$ 812

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 16/10

2:00 p.m.-7:37 p.m.

2 stops30h 37m

San José Juan Santamaria Intl

Fri 23/10

7:55 a.m.-12:37 p.m.

2 stops27h 42m

C$ 821

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 16/1

2:15 p.m.-8:39 p.m.

2 stops30h 24m

San José Juan Santamaria Intl

Sat 23/1

7:30 a.m.-11:39 a.m.

2 stops28h 09m

C$ 852
Cheapest one-way
Quickest one-way

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 7/9

8:15 a.m.-10:00 p.m.

1 stop14h 45m

C$ 376

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/7

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

Best time to book a flight from Winnipeg to San José

Have a flexible travel schedule? Discover the best time to fly to San José from Winnipeg with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What’s the top layover airport for flights from Winnipeg to San José?

Share of one-stop round-trip flights from Winnipeg to San José chosen by Cheapflights users in the past 12 months, using the same layover each way.

Toronto (YYZ) – chosen by Cheapflights users on 93% of one-stop itineraries from Winnipeg to San José on Cheapflights.

What’s the cheapest layover airport for flights from Winnipeg to San José?

Average round-trip fare for 1-stop flights from Winnipeg to San José, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Toronto (YYZ) is the most affordable 1-stop option, with an average round-trip price of C$ 1,307.

What’s the fastest layover option from Winnipeg to San José?

Shortest average travel time for 1-stop one-way flights from Winnipeg to San José, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Toronto (YYZ) have the shortest average one-way travel time for 1-stop routes: 11h 20m.

Which airport typically offers the quickest layover for flights from Winnipeg to San José?

Average layover duration for 1-stop one-way flights from Winnipeg to San José, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 3h 48m.

Reviews of airlines servicing San José

Get insights into the airlines that provide service to San José. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San José. Reviews last updated 27 July 2026.
See what other customers who have flown with United Airlines and Air Canada from Winnipeg to San José have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
10,042 reviews
Check prices

Food

6.6

Crew

8.1

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
10,042 reviews
United Airlines
7.4
Good
10,042 reviews
Check prices

Food

6.6

Crew

8.1

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
Air Canada
7.1
Good
11,391 reviews
United Airlines
7.4
Good
10,042 reviews
Check prices

Food

6.6

Crew

8.1

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to San José. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Winnipeg to San José?

    Airlines like Air Canada and United Airlines fly from Winnipeg to San José in about 28h 36m. The time it takes to get you to your destination can typically vary by up to 34m. The distance between Winnipeg and San José is about 4595 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the cheapest airlines flying from Winnipeg to San José round-trip?

    United Airlines, at C$ 685, was found to be the cheapest airline from Winnipeg to San José. An alternate airline flying to your destination would be Air Canada. Users have found that United Airlines is 45% cheaper than the other options available to this destination.

  • Can I find deals for flights from Winnipeg to San José that include hotel bookings?

    Yes. In addition to deals on Winnipeg to San José flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to San José?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to San José.

  • Can I find deals for business class flights from Winnipeg to San José?

    Yes. Cheapflights offers flight deals from Winnipeg to San José by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Travelling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Alajuela
Jacó
Heredia
Dominical
Monteverde

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Winnipeg to San José

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to Liberia flights

Top 2 airlines flying from Winnipeg to San José

Discover the top 2 airlines that operate flights from Winnipeg to San José. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 27 July 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 685AverageC$ 794FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 836AverageC$ 1,308FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Winnipeg to San José?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to San José from Winnipeg today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to San José?

Cheapflights simply makes it quick and affordable to book flights from Winnipeg to San José by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Winnipeg to San José with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Winnipeg to San José flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Winnipeg to San José become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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