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Cheap flights from Winnipeg to San José from C$ 397

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 29/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJO
16 Apr — 23 Apr1
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 17 March 2026.

Mon 15/62:00 p.m.
YWG
-
SJO
1 stop9h 00m
Air Canada
Mon 22/67:40 a.m.
SJO
-
YWG
1 stop25h 25m
Air Canada
Deal found 16/3C$ 749
Thu 11/64:05 p.m.
YWG
-
SJO
1 stop29h 30m
Air Canada
Thu 18/67:40 a.m.
SJO
-
YWG
1 stop12h 49m
Air Canada
Deal found 16/3C$ 756
Mon 15/68:45 a.m.
YWG
-
SJO
2 stops26h 26m
United Airlines
Mon 22/67:55 a.m.
SJO
-
YWG
2 stops37h 38m
United Airlines
Deal found 16/3C$ 797
Thu 5/116:00 a.m.
YWG
-
SJO
2 stops18h 20m
Air Canada
Thu 12/118:35 a.m.
SJO
-
YWG
1 stop14h 04m
Air Canada
Deal found 14/3C$ 811
Mon 13/48:20 p.m.
YWG
-
SJO
2 stops28h 35m
Multiple Airlines
Tue 21/44:00 p.m.
SJO
-
YWG
2 stops23h 25m
Multiple Airlines
Deal found 14/3C$ 842
Wed 15/48:10 p.m.
YWG
-
SJO
1 stop27h 25m
Multiple Airlines
Wed 22/44:00 p.m.
SJO
-
YWG
2 stops18h 32m
Multiple Airlines
Deal found 14/3C$ 854
Mon 13/48:00 a.m.
YWG
-
SJO
1 stop28h 14m
Multiple Airlines
Sat 18/41:40 a.m.
SJO
-
YWG
2 stops37h 45m
Multiple Airlines
Deal found 14/3C$ 876

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 17 March 2026.

Round-trip from

C$ 749

One-way from

C$ 397

Popular in

December

Cheapest in

July

Average price

C$ 1,250
Air Canada
  • Air Canada
  • 15/6-22/6
  • 2 total stops
  • 34h 25m total
  • Winnipeg to San José
Search Deals
29/4
  • 29/4
  • 1 total stop
  • 27h 25m total
  • Winnipeg to San José
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 332 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 17 March 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

Mon 15/6

8:45 a.m.-10:11 a.m.

2 stops26h 26m

San José Juan Santamaria Intl

Mon 22/6

7:55 a.m.-10:33 p.m.

2 stops37h 38m

C$ 797

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 20/4

2:00 p.m.-12:21 p.m.

2 stops23h 21m

San José Juan Santamaria Intl

Tue 28/4

11:13 a.m.-11:52 a.m.

2 stops23h 39m

C$ 924

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 5/4

5:00 a.m.-10:55 p.m.

2 stops18h 55m

San José Juan Santamaria Intl

Thu 16/4

11:55 p.m.-12:40 a.m.

2 stops23h 45m

C$ 931

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 13/4

10:20 a.m.-8:30 a.m.

3 stops23h 10m

San José Juan Santamaria Intl

Tue 21/4

4:00 p.m.-7:25 p.m.

2 stops26h 25m

C$ 941

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 13/4

2:00 p.m.-12:21 p.m.

2 stops23h 21m

San José Juan Santamaria Intl

Mon 20/4

11:13 a.m.-11:52 a.m.

2 stops23h 39m

C$ 946

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 11/4

8:45 a.m.-10:11 a.m.

2 stops26h 26m

San José Juan Santamaria Intl

Wed 15/4

11:13 a.m.-11:52 a.m.

2 stops23h 39m

C$ 946
Quickest round-trip

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 13/4

2:00 p.m.-10:11 a.m.

2 stops21h 11m

San José Juan Santamaria Intl

Sun 19/4

1:25 p.m.-11:52 a.m.

2 stops21h 27m

C$ 949

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 3/5

2:00 p.m.-12:21 p.m.

2 stops23h 21m

San José Juan Santamaria Intl

Sat 9/5

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

2 stops26h 57m

C$ 950

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 8/4

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

2 stops28h 36m

San José Juan Santamaria Intl

Wed 15/4

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

2 stops26h 57m

C$ 997
Cheapest one-way
Quickest one-way

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 29/4

8:10 p.m.-11:55 p.m.

2 stops28h 45m

C$ 404

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/3

Showing 1-10 of 12 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 is the cheapest month to book a flight from Winnipeg to San José?

Currently, July is the cheapest month in which you can book a flight from Winnipeg to San José (average of C$ 663). Flying from Winnipeg to San José in June is currently the most expensive (average of C$ 948). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 17 March 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
9,435 reviews
Check prices

Boarding

7.7

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

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
9,435 reviews
United Airlines
7.4
Good
9,435 reviews
Check prices

Boarding

7.7

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

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
10,813 reviews
United Airlines
7.4
Good
9,435 reviews
Check prices

Boarding

7.7

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

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 United Airlines fly from Winnipeg to San José in about 26h 26m. 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$ 665, 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 39% 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.

  • What is the cheapest month to book a flight from Winnipeg to San José?

    Currently, July is the cheapest month in which you can book a flight from Winnipeg to San José (average of C$ 663). Flying from Winnipeg to San José in June is currently the most expensive (average of C$ 948). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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

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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 17 March 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 665AverageC$ 810FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 1,025AverageC$ 1,423FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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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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