Find flights
When to book
Airlines
FAQs

Cheap flights from Winnipeg to San José from C$ 443

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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJO
21 Jun — 28 Jun1
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 22 May 2026.

Sun 8/115:15 a.m.
YWG
-
SJO
1 stop16h 50m
Air Canada
Tue 17/118:35 a.m.
SJO
-
YWG
1 stop14h 04m
Air Canada
Deal found 20/5C$ 742
Sat 7/117:20 p.m.
YWG
-
SJO
2 stops27h 55m
Air Canada
Mon 16/118:35 a.m.
SJO
-
YWG
1 stop14h 04m
Air Canada
Deal found 20/5C$ 784
Tue 27/108:15 a.m.
YWG
-
SJO
1 stop15h 00m
Air Canada
Tue 10/118:35 a.m.
SJO
-
YWG
1 stop14h 04m
Air Canada
Deal found 17/5C$ 796
Tue 2/68:10 a.m.
YWG
-
SJO
1 stop14h 50m
Air Canada
Fri 12/67:10 a.m.
SJO
-
YWG
2 stops25h 59m
Air Canada
Deal found 18/5C$ 825
Thu 29/109:25 a.m.
YWG
-
SJO
1 stop12h 40m
Air Canada
Tue 10/118:35 a.m.
SJO
-
YWG
1 stop12h 24m
Air Canada
Deal found 18/5C$ 850

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 22 May 2026.

Round-trip from

C$ 742

One-way from

C$ 443

Popular in

June

Cheapest in

April

Average price

C$ 1,091
Air Canada
  • Air Canada
  • 8/11-17/11
  • 2 total stops
  • 30h 54m total
  • Winnipeg to San José
Search Deals
Air Canada
  • Air Canada
  • 4/6
  • 1 total stop
  • 9h 00m total
  • Winnipeg to San José
Search Deals
Highest demand for flights based on searches. 1% potential increase in price (C$ 16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 22 May 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
Quickest round-trip

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 8/11

7:30 a.m.-10:05 p.m.

1 stop14h 35m

San José Juan Santamaria Intl

Tue 17/11

8:35 a.m.-10:39 p.m.

1 stop14h 04m

C$ 742

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 7/11

7:20 p.m.-11:15 p.m.

2 stops27h 55m

San José Juan Santamaria Intl

Mon 16/11

8:35 a.m.-10:16 a.m.

2 stops25h 41m

C$ 789

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 18/6

8:45 a.m.-10:39 p.m.

2 stops38h 54m

San José Juan Santamaria Intl

Wed 24/6

12:30 a.m.-10:38 p.m.

2 stops21h 08m

C$ 861

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 26/10

8:30 a.m.-7:39 p.m.

2 stops36h 09m

San José Juan Santamaria Intl

Thu 29/10

11:35 a.m.-8:48 p.m.

2 stops32h 13m

C$ 861

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 1/6

12:56 p.m.-7:37 p.m.

2 stops31h 41m

San José Juan Santamaria Intl

Sat 6/6

6:40 a.m.-8:57 p.m.

1 stop13h 17m

C$ 870

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 5/6

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

2 stops37h 37m

San José Juan Santamaria Intl

Fri 12/6

7:55 a.m.-11:52 a.m.

2 stops26h 57m

C$ 870
Cheapest one-way
Quickest one-way

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 4/6

2:00 p.m.-10:00 p.m.

1 stop9h 00m

C$ 443

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 4/6

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

2 stops37h 37m

C$ 450

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 4/6

9:25 a.m.-12:02 p.m.

3 stops27h 37m

C$ 592

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/5

Sorted by cheapest first

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

How much does it cost to fly round-trip from Winnipeg to San José?

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 22 May 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
9,751 reviews
Check prices

Overall

7.4

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

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
9,751 reviews
United Airlines
7.4
Good
9,751 reviews
Check prices

Overall

7.4

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

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
11,075 reviews
United Airlines
7.4
Good
9,751 reviews
Check prices

Overall

7.4

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

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 fly from Winnipeg to San José in about 14h 35m. The time it takes to get you to your destination can typically vary by up to . The distance between Winnipeg and San José is about 4595 km.

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

    United Airlines, at C$ 670, 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 36% 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
Alajuela
Manuel Antonio
Jacó
Heredia
Dominical
Monteverde

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 22 May 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 670AverageC$ 765FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 975AverageC$ 1,278FlexibilityNo 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!

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.