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

Flights via Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 3h 01m.

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

Toronto (YYZ) – chosen by Cheapflights users on 84% of one-stop itineraries from Winnipeg to San José, San José Province on Cheapflights.

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

Flights via Toronto (YYZ) have the shortest average one-way travel time for 1-stop routes: 10h 58m.

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

Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of C$ 1,082.

How long is the flight from Winnipeg to San José, San José Province?

A quick flight from Winnipeg to San José, San José Province can take about 27h 56m. United Airlines provides one of the quickest options available for as low as C$ 666. There are 4595 km between Winnipeg and San José, San José Province.

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

Currently priced at C$ 663, United Airlines will fly you from Winnipeg to San José, San José Province and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Air Canada and Avianca - these airlines can fly you to your destination from C$ 1,002 and C$ 1,226, respectively. United Airlines is priced at 42% lower than the current average price of a flight leaving 3 months from now.

What is the cheapest day to fly from Winnipeg to San José, San José Province?

Travelers seeking maximum savings on their Winnipeg to San José, San José Province flight should consider departing on Tuesday at noon when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

In terms of precipitation, rainfall in San José, San José Province ranges from 0.0 - 300.0 mm per month. September is typically the wettest month, when rainfall can reach 300.0 mm. February is typically the driest time to visit San José, San José Province when rainfall is around 0.0 mm.

If weather is an important factor for your trip to San José, San José Province, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 21.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 18.0 C).

What are the most popular airlines that fly from Winnipeg to San José, San José Province?

Before booking your flight from Winnipeg to San José, San José Province check out the most popular airlines for this route: Air Canada, Avianca or United Airlines.

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.

C$ 276+ Cheap Flights from Winnipeg to San José

Cheapflights Tip: The best prices from Winnipeg to San José Juan Santamaria Intl are usually found in July or September, booked 61 days in advance, depart on a Tuesday or Friday and return on a Monday

Cheap flight deals from Winnipeg to San José

Round-trip from	C$ 662
One-way from	C$ 276
Popular in	December
Cheapest in	July
Average price	C$ 841

1/11-15/11
3 total stops
45h 23m total
Winnipeg to San José

Search Deals

23/10
2 total stops
27h 30m total
Winnipeg to San José

Search Deals

Highest demand for flights based on searches. 14% potential increase in price (C$ 267 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease (C$ 55 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in September 2025

Search Deals

Find flight deals from Winnipeg to San José

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 September 2025.

Sat 1/115:00 a.m.YWG - SJO

1 stop19h 35mMultiple Airlines

Sat 15/111:19 p.m.SJO - YWG

2 stops25h 48mMultiple Airlines

Deal found 16/9C$ 662

Mon 15/128:00 a.m.YWG - SJO

2 stops17h 20mMultiple Airlines

Sun 21/121:19 p.m.SJO - YWG

1 stop28h 44mMultiple Airlines

Deal found 15/9C$ 790

Tue 16/95:15 p.m.YWG - SJO

2 stops31h 20mMultiple Airlines

Tue 23/912:19 p.m.SJO - YWG

3 stops28h 21mMultiple Airlines

Deal found 15/9C$ 857

Mon 15/95:15 p.m.YWG - SJO

2 stops45h 15mMultiple Airlines

Mon 22/97:30 a.m.SJO - YWG

2 stops29h 13mMultiple Airlines

Deal found 14/9C$ 891

Tue 16/97:00 p.m.YWG - SJO

2 stops38h 40mAvianca

Tue 23/95:05 a.m.SJO - YWG

2 stops28h 30mAvianca

Deal found 15/9C$ 993

Best flights from Winnipeg to San José
Discover carefully curated flight deals from Winnipeg to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 17 September 2025.

Sat 1/115:00 a.m.YWG - SJO

1 stop19h 35mMultiple Airlines

Sat 15/111:19 p.m.SJO - YWG

2 stops25h 48mMultiple Airlines

Deal found 16/9C$ 662

Tue 3/32:20 p.m.YWG - SJO

2 stops27h 56mUnited Airlines

Tue 10/31:20 p.m.SJO - YWG

2 stops21h 19mUnited Airlines

Deal found 15/9C$ 666

Sun 11/12:20 p.m.YWG - SJO

2 stops46h 55mUnited Airlines

Sun 18/16:30 a.m.SJO - YWG

2 stops29h 27mUnited Airlines

Deal found 14/9C$ 691

Mon 15/128:00 a.m.YWG - SJO

2 stops17h 20mMultiple Airlines

Sun 21/121:19 p.m.SJO - YWG

1 stop28h 44mMultiple Airlines

Deal found 15/9C$ 790

Thu 22/12:20 p.m.YWG - SJO

1 stop22h 36mUnited Airlines

Wed 18/22:20 p.m.SJO - YWG

2 stops21h 37mUnited Airlines

Deal found 16/9C$ 770

Last-minute flights from Winnipeg to San José
Discover last-minute flight deals from Winnipeg to San José. Data last updated 17 September 2025 and is based on user searches.

Tue 16/95:15 p.m.YWG - SJO

2 stops31h 20mMultiple Airlines

Tue 23/912:19 p.m.SJO - YWG

3 stops28h 21mMultiple Airlines

Deal found 15/9C$ 857

Tue 16/97:00 p.m.YWG - SJO

2 stops38h 40mAvianca

Tue 23/95:05 a.m.SJO - YWG

2 stops28h 30mAvianca

Deal found 15/9C$ 993

One-way flights from Winnipeg to San José
Search for one-way flight options from Winnipeg to San José. Find affordable one-way fares based on user searches. Data last updated 17 September 2025.

Thu 23/109:00 a.m.YWG - SJO

2 stops27h 30mMultiple Airlines

Deal found 17/9C$ 276

Fri 31/104:00 p.m.YWG - SJO

1 stop24h 13mMultiple Airlines

Deal found 16/9C$ 294

Tue 21/106:30 a.m.YWG - SJO

2 stops30h 00mMultiple Airlines

Deal found 15/9C$ 299

Wed 22/109:05 p.m.YWG - SJO

3 stops39h 25mMultiple Airlines

Deal found 15/9C$ 314

Fly from

Fly to

Route

Depart

Return

Price

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 1/11

5:00 a.m.-11:35 p.m.

1 stop19h 35m

San José Juan Santamaria Intl

Sat 15/11

1:19 p.m.-3:07 p.m.

2 stops25h 48m

C$ 662

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 3/3

2:20 p.m.-6:16 p.m.

2 stops27h 56m

San José Juan Santamaria Intl

Tue 10/3

1:20 p.m.-11:39 a.m.

2 stops21h 19m

C$ 666

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 11/1

2:20 p.m.-1:15 p.m.

2 stops46h 55m

San José Juan Santamaria Intl

Sun 18/1

6:30 a.m.-11:57 a.m.

2 stops29h 27m

C$ 691

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 22/1

2:20 p.m.-12:56 p.m.

1 stop22h 36m

San José Juan Santamaria Intl

Wed 18/2

2:20 p.m.-11:57 a.m.

2 stops21h 37m

C$ 770

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 15/12

8:00 a.m.-1:20 a.m.

2 stops17h 20m

San José Juan Santamaria Intl

Sun 21/12

1:19 p.m.-6:03 p.m.

1 stop28h 44m

C$ 790

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 23/10

9:00 a.m.-11:30 a.m.

2 stops27h 30m

C$ 276

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 31/10

4:00 p.m.-3:13 p.m.

1 stop24h 13m

C$ 294

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 21/10

6:30 a.m.-11:30 a.m.

2 stops30h 00m

C$ 299

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 22/10

9:05 p.m.-11:30 a.m.

3 stops39h 25m

C$ 314

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/9

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

Prices

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

The best time to book flights from Winnipeg to San José, San José Province is 61 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, May is the cheapest month in which you can book a flight from Winnipeg to San José, San José Province (average of C$ 486). Flying from Winnipeg to San José, San José Province in December is currently the most expensive (average of C$ 683). 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.

What is the cheapest time of day to fly from YWG to SJO?

A simple way to save on the total cost of your ticket is to fly from Winnipeg to San José, San José Province at noon. If you’re flexible enough to do this you can expect to save up to 43% on your trip compared to booking a flight in the morning.

Reviews of airlines servicing San José

See what other customers who have flown with United Airlines,Air Canada, andAvianca 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

8,926 reviews

Check prices

Reviews

1 / 20

8.0

Excellent

Anonymous,Dec 2024

YVR - SFO

It was a good experience. The flight took 45 minutes longer to fly and all passengers had to wait inside the plane till the technical issue was fixed. Overall it was a good experience.

United Airlines

7.4

Good

8,926 reviews

United Airlines

7.4

Good

8,926 reviews

Check prices

Reviews

1 / 20

8.0

Excellent

Anonymous,Dec 2024

YVR - SFO

It was a good experience. The flight took 45 minutes longer to fly and all passengers had to wait inside the plane till the technical issue was fixed. Overall it was a good experience.

Air Canada

7.1

Good

10,000 reviews

United Airlines

7.4

Good

8,926 reviews

Check prices

Reviews

1 / 20

8.0

Excellent

Anonymous,Dec 2024

YVR - SFO

It was a good experience. The flight took 45 minutes longer to fly and all passengers had to wait inside the plane till the technical issue was fixed. Overall it was a good experience.

Avianca

6.7

Okay

2,436 reviews

United Airlines

7.4

Good

8,926 reviews

Check prices

Reviews

1 / 20

8.0

Excellent

Anonymous,Dec 2024

YVR - SFO

It was a good experience. The flight took 45 minutes longer to fly and all passengers had to wait inside the plane till the technical issue was fixed. Overall it was a good experience.

Related info for your journey

How long is the flight from Winnipeg to San José, San José Province?
A quick flight from Winnipeg to San José, San José Province can take about 27h 56m. United Airlines provides one of the quickest options available for as low as C$ 666. There are 4595 km between Winnipeg and San José, San José Province.
What are the cheapest airlines flying from Winnipeg to San José, San José Province round-trip?
Currently priced at C$ 663, United Airlines will fly you from Winnipeg to San José, San José Province and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Air Canada and Avianca - these airlines can fly you to your destination from C$ 1,002 and C$ 1,226, respectively. United Airlines is priced at 42% lower than the current average price of a flight leaving 3 months from now.
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, San José Province?
Currently, May is the cheapest month in which you can book a flight from Winnipeg to San José, San José Province (average of C$ 486). Flying from Winnipeg to San José, San José Province in December is currently the most expensive (average of C$ 683). 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

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Dominical

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Monteverde

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Top 3 airlines flying from Winnipeg to San José

Airline	Cheapest	Average	Flexibility	On-time
United Airlines	CheapestC$ 663	AverageC$ 783	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights
Air Canada	CheapestC$ 1,002	AverageC$ 1,422	FlexibilityNo cancel fee	On-time67%	Search Air Canada flights
Avianca	CheapestC$ 1,226	AverageC$ 1,580	FlexibilityNo cancel fee	On-time71%	Search Avianca flights

Fly with Cheapflights

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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Cheap flights from Winnipeg to San José from C$ 276

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 23/10. Fares are subject to change and may not be available on all flights or dates of travel.

Cheapflights Tip: The best prices from Winnipeg to San José Juan Santamaria Intl are usually found in July or September, booked 61 days in advance, depart on a Tuesday or Friday and return on a Monday

Cheap flight deals from Winnipeg to San José

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Winnipeg to San José

Cheapest flights from Winnipeg to San JoséExplore 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 September 2025.

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 September 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Winnipeg to San José that are best for you.

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.

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, San José Province?

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

What is the cheapest time of day to fly from YWG to SJO?

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

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

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

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

Reviews of airlines servicing San José

See what other customers who have flown with United Airlines,Air Canada, andAvianca 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.

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, San José Province?

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

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

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

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

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

Travelling to a place near San José?

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.

Top 3 airlines flying from Winnipeg to San José

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

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

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

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

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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 September 2025.