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Cheap flights from Winnipeg to San José from C$ 365

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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJO
30 Mar — 6 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 28 February 2026.

Sun 12/48:45 a.m.
YWG
-
SJO
2 stops26h 26m
United Airlines
Wed 22/411:13 a.m.
SJO
-
YWG
2 stops32h 44m
United Airlines
Deal found 25/2C$ 583
Tue 14/48:45 a.m.
YWG
-
SJO
2 stops28h 36m
United Airlines
Thu 16/41:25 p.m.
SJO
-
YWG
2 stops30h 32m
United Airlines
Deal found 25/2C$ 613
Mon 13/48:00 a.m.
YWG
-
SJO
1 stop28h 14m
Multiple Airlines
Thu 23/412:20 p.m.
SJO
-
YWG
2 stops25h 49m
Multiple Airlines
Deal found 25/2C$ 692
Thu 2/42:00 p.m.
YWG
-
SJO
2 stops21h 11m
United Airlines
Wed 8/47:55 a.m.
SJO
-
YWG
2 stops26h 57m
United Airlines
Deal found 24/2C$ 709
Mon 27/78:45 a.m.
YWG
-
SJO
2 stops26h 26m
United Airlines
Thu 6/87:55 a.m.
SJO
-
YWG
2 stops37h 38m
United Airlines
Deal found 25/2C$ 713
Sat 7/117:20 p.m.
YWG
-
SJO
2 stops27h 55m
Air Canada
Sat 14/118:50 a.m.
SJO
-
YWG
2 stops11h 38m
Air Canada
Deal found 27/2C$ 722
Tue 14/48:20 p.m.
YWG
-
SJO
2 stops27h 35m
Multiple Airlines
Thu 16/412:20 p.m.
SJO
-
YWG
3 stops25h 49m
Multiple Airlines
Deal found 24/2C$ 773
Sat 12/127:20 p.m.
YWG
-
SJO
2 stops27h 55m
Air Canada
Sat 19/128:50 a.m.
SJO
-
YWG
1 stop31h 46m
Air Canada
Deal found 27/2C$ 776
Tue 28/46:05 p.m.
YWG
-
SJO
3 stops25h 45m
Multiple Airlines
Tue 12/57:00 a.m.
SJO
-
YWG
2 stops16h 55m
Multiple Airlines
Deal found 26/2C$ 822
Wed 25/32:20 p.m.
YWG
-
SJO
2 stops30h 19m
United Airlines
Wed 1/47:55 a.m.
SJO
-
YWG
2 stops26h 57m
United Airlines
Deal found 24/2C$ 847

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 28 February 2026.

Round-trip from

C$ 583

One-way from

C$ 365

Popular in

December

Cheapest in

July

Average price

C$ 1,210
United Airlines
  • United Airlines
  • 14/4-16/4
  • 4 total stops
  • 50h 05m total
  • Winnipeg to San José
Search Deals
Air Canada
  • Air Canada
  • 7/4
  • 1 total stop
  • 9h 25m total
  • Winnipeg to San José
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 342 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 45 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 28 February 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

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

Thu 23/4

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

2 stops26h 57m

C$ 583

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 2/4

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

2 stops21h 11m

San José Juan Santamaria Intl

Wed 8/4

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

2 stops26h 57m

C$ 709

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 28/4

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

2 stops21h 11m

San José Juan Santamaria Intl

Tue 12/5

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

2 stops21h 27m

C$ 713

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 25/3

2:20 p.m.-7:39 p.m.

2 stops30h 19m

San José Juan Santamaria Intl

Wed 1/4

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

2 stops26h 57m

C$ 847

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 14/4

6:00 a.m.-10:10 p.m.

2 stops17h 10m

San José Juan Santamaria Intl

Tue 21/4

1:31 p.m.-11:32 a.m.

2 stops21h 01m

C$ 890

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 2/4

5:00 a.m.-10:35 p.m.

1 stop18h 35m

San José Juan Santamaria Intl

Tue 7/4

1:50 a.m.-11:32 a.m.

2 stops32h 42m

C$ 929

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 14/4

8:05 p.m.-10:55 p.m.

2 stops27h 50m

San José Juan Santamaria Intl

Thu 16/4

4:00 p.m.-11:32 a.m.

2 stops18h 32m

C$ 994

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 28/4

1:30 p.m.-9:35 p.m.

1 stop9h 05m

San José Juan Santamaria Intl

Tue 12/5

8:00 a.m.-10:03 a.m.

1 stop25h 03m

C$ 1,034

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 30/3

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

2 stops21h 11m

San José Juan Santamaria Intl

Mon 6/4

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

2 stops21h 27m

C$ 1,038

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 14/4

1:45 p.m.-10:10 p.m.

1 stop9h 25m

San José Juan Santamaria Intl

Tue 21/4

7:55 a.m.-9:53 a.m.

1 stop24h 58m

C$ 1,073

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/2

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

How far ahead should I book a flight from Winnipeg to San José?

Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to San José. Price data was last updated on 20 February 2026.

To ensure you get the cheapest price possible for a flight from Winnipeg to San José, you should look to book at least 64 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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$ 661). Flying from Winnipeg to San José in June is currently the most expensive (average of C$ 946). 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.

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 28 February 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
9,363 reviews
Check prices

Crew

8.1

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.6

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
9,363 reviews
United Airlines
7.4
Good
9,363 reviews
Check prices

Crew

8.1

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.6

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
10,757 reviews
United Airlines
7.4
Good
9,363 reviews
Check prices

Crew

8.1

Boarding

7.7

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.6

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 21h 11m. 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$ 664, 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 40% 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$ 661). Flying from Winnipeg to San José in June is currently the most expensive (average of C$ 946). 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
Alajuela
Jacó
Heredia
Dominical
Manuel Antonio
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 28 February 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 664AverageC$ 798FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 1,022AverageC$ 1,427FlexibilityNo 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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