What is the cheapest airline that flies from Winnipeg to San José Juan Santamaria Intl?

Air Canada and United Airlines are the most popular carriers operating from Winnipeg to San José Juan Santamaria Intl

When did momondo last update prices for flights from Winnipeg Airport to San José Juan Santamaria Intl Airport?

Prices for flights from Winnipeg Airport to San José Juan Santamaria Intl Airport are updated daily.

How many operators does momondo search for flights from Winnipeg Airport to San José Juan Santamaria Intl Airport?

As of August 2026, there are 2 operators available to choose from for flights from Winnipeg Airport to San José Juan Santamaria Intl Airport.

How old do you have to be to fly from Winnipeg Airport to San José Juan Santamaria Intl Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to San José Juan Santamaria Intl Airport.

What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

The required travel and health documents for your San José Juan Santamaria Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at San José Juan Santamaria Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

C$ 376 Cheap Flights from Winnipeg to San José in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Winnipeg to San José

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7:15 a.m. - 10:30 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

15h 15m1 stop Toronto Pearson Intl

8:45 a.m. - 12:24 a.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

15h 39m1 stop Toronto Pearson Intl

C$ 649Air Canada

Mon, 1 Feb - Sun, 7 Feb

7:15 a.m. - 10:30 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

15h 15m1 stop Toronto Pearson Intl

8:45 a.m. - 12:24 a.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

15h 39m1 stop Toronto Pearson Intl

C$ 652Air Canada

Mon, 1 Feb - Sun, 7 Feb

7:15 a.m. - 10:30 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

15h 15m1 stop Toronto Pearson Intl

8:45 a.m. - 10:00 a.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

25h 15m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

C$ 653Air Canada

Mon, 1 Feb - Sun, 7 Feb

6:55 p.m. - 12:40 a.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

29h 45m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

8:45 a.m. - 12:24 a.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

15h 39m1 stop Toronto Pearson Intl

C$ 653Air Canada

Mon, 1 Feb - Sun, 7 Feb

7:15 a.m. - 11:40 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

16h 25m2 stops Toronto Pearson Intl San Salvador El Salvador Intl

5:00 a.m. - 9:14 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

16h 14m2 stops San Salvador El Salvador Intl Toronto Pearson Intl

C$ 738Avianca

Sun, 8 Nov - Tue, 17 Nov

7:15 a.m. - 11:40 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

16h 25m2 stops Toronto Pearson Intl San Salvador El Salvador Intl

5:10 a.m. - 9:14 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

16h 04m2 stops San Salvador El Salvador Intl Toronto Pearson Intl

C$ 738Avianca

Sun, 8 Nov - Tue, 17 Nov

7:15 a.m. - 11:40 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

16h 25m2 stops Toronto Pearson Intl San Salvador El Salvador Intl

5:00 a.m. - 9:14 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

16h 14m2 stops San Salvador El Salvador Intl Toronto Pearson Intl

C$ 739Avianca

Sun, 8 Nov - Tue, 17 Nov

8:40 a.m. - 8:39 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

35h 59m2 stops Denver Intl Houston George Bush Intcntl

8:45 a.m. - 8:57 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

36h 12m2 stops Houston George Bush Intcntl Denver Intl

C$ 743United Airlines

Sun, 15 Nov - Wed, 25 Nov

2:15 p.m. - 8:39 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

30h 24m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

8:45 a.m. - 12:23 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

27h 38m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

C$ 779United Airlines

Sat, 14 Nov - Wed, 25 Nov

2:15 p.m. - 8:39 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

30h 24m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

8:45 a.m. - 12:23 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

27h 38m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

C$ 779United Airlines

Sat, 14 Nov - Tue, 24 Nov

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Air Canada flights from Winnipeg to San José

Our best Air Canada deals on Winnipeg to San José flight tickets

Air Canada

1 Feb

YWG7:15 a.m.Winnipeg

15h 15m

1 stop

SJO10:30 p.m.San José Juan Santamaria Intl

7 Feb

SJO8:45 a.m.San José Juan Santamaria Intl

15h 39m

1 stop

YWG12:24 a.m.Winnipeg

C$ 649

Air Canada

1 Feb

YWG7:15 a.m.Winnipeg

15h 15m

1 stop

SJO10:30 p.m.San José Juan Santamaria Intl

7 Feb

SJO8:45 a.m.San José Juan Santamaria Intl

15h 39m

1 stop

YWG12:24 a.m.Winnipeg

C$ 652

Air Canada

1 Feb

YWG6:55 p.m.Winnipeg

29h 45m

2 stops

SJO12:40 a.m.San José Juan Santamaria Intl

7 Feb

SJO8:45 a.m.San José Juan Santamaria Intl

15h 39m

1 stop

YWG12:24 a.m.Winnipeg

C$ 653

Avianca flights from Winnipeg to San José

Our best Avianca deals on Winnipeg to San José flight tickets

Avianca

8 Nov

YWG7:15 a.m.Winnipeg

16h 25m

2 stops

SJO11:40 p.m.San José Juan Santamaria Intl

17 Nov

SJO5:00 a.m.San José Juan Santamaria Intl

16h 14m

2 stops

YWG9:14 p.m.Winnipeg

C$ 738

Avianca

8 Nov

YWG7:15 a.m.Winnipeg

16h 25m

2 stops

SJO11:40 p.m.San José Juan Santamaria Intl

17 Nov

SJO5:00 a.m.San José Juan Santamaria Intl

16h 14m

2 stops

YWG9:14 p.m.Winnipeg

C$ 739

Avianca

8 Nov

YWG7:15 a.m.Winnipeg

16h 25m

2 stops

SJO11:40 p.m.San José Juan Santamaria Intl

17 Nov

SJO5:00 a.m.San José Juan Santamaria Intl

16h 14m

2 stops

YWG9:14 p.m.Winnipeg

C$ 742

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 1/2

7:15 a.m.-10:30 p.m.

1 stop15h 15m

San José Juan Santamaria Intl

Sun 7/2

8:45 a.m.-12:24 a.m.

1 stop15h 39m

C$ 649

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 1/2

7:15 a.m.-10:30 p.m.

1 stop15h 15m

San José Juan Santamaria Intl

Sun 7/2

8:45 a.m.-12:24 a.m.

1 stop15h 39m

C$ 652

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 1/2

7:15 a.m.-10:30 p.m.

1 stop15h 15m

San José Juan Santamaria Intl

Sun 7/2

8:45 a.m.-10:00 a.m.

2 stops25h 15m

C$ 653

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 1/2

6:55 p.m.-12:40 a.m.

2 stops29h 45m

San José Juan Santamaria Intl

Sun 7/2

8:45 a.m.-12:24 a.m.

1 stop15h 39m

C$ 653

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 8/11

7:15 a.m.-11:40 p.m.

2 stops16h 25m

San José Juan Santamaria Intl

Tue 17/11

5:00 a.m.-9:14 p.m.

2 stops16h 14m

C$ 738

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 8/11

7:15 a.m.-11:40 p.m.

2 stops16h 25m

San José Juan Santamaria Intl

Tue 17/11

5:10 a.m.-9:14 p.m.

2 stops16h 04m

C$ 738

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 8/11

7:15 a.m.-11:40 p.m.

2 stops16h 25m

San José Juan Santamaria Intl

Tue 17/11

5:00 a.m.-9:14 p.m.

2 stops16h 14m

C$ 739

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 15/11

8:40 a.m.-8:39 p.m.

2 stops35h 59m

San José Juan Santamaria Intl

Wed 25/11

8:45 a.m.-8:57 p.m.

2 stops36h 12m

C$ 743

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sat 14/11

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

2 stops30h 24m

San José Juan Santamaria Intl

Wed 25/11

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

2 stops27h 38m

C$ 779

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sat 14/11

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

2 stops30h 24m

San José Juan Santamaria Intl

Tue 24/11

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

2 stops27h 38m

C$ 779

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Winnipeg to San José

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest month to fly to San José?

In general, May is the cheapest month to fly from Winnipeg to San José. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 0. If you aren’t able to travel during the month of May, then book flights to San José from Winnipeg during April instead. Flights to San José in April, while not as cheap as those in May, still average around C$ 771.

Can stopping save me money on Winnipeg to San José flights?

You could potentially save up to 4% on your flight if you consider stops on a Winnipeg to San José flight.

When to book flights from Winnipeg to San José

Are you open to changing your travel dates? Check out the ideal times to fly from Winnipeg to San José according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Winnipeg to San José (YWG to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to San José

Best price found	C$ 376
Fastest flight time	12h 55m
Direct flights	None

The best one-way flight to San José from Winnipeg in the past 72 hours is C$ 376. The best round-trip flight deal from Winnipeg to San José found on momondo in the last 72 hours is C$ 649.

The fastest flight from Winnipeg to San José takes 12h 55m

There are no direct flights from Winnipeg to San José. There are no popular flight routes from Winnipeg to San José.

Search flight deals

Frequently asked questions about flying from Winnipeg to San José

How far is Winnipeg to San José Juan Santamaria Intl by plane?
There are 4599.7 km between Winnipeg and San José Juan Santamaria Intl. 12h 55m is a normal flight duration for this route.
When did momondo last update prices for flights from Winnipeg Airport to San José Juan Santamaria Intl Airport?
Prices for flights from Winnipeg Airport to San José Juan Santamaria Intl Airport are updated daily.
How many operators does momondo search for flights from Winnipeg Airport to San José Juan Santamaria Intl Airport?
As of August 2026, there are 2 operators available to choose from for flights from Winnipeg Airport to San José Juan Santamaria Intl Airport.
How old do you have to be to fly from Winnipeg Airport to San José Juan Santamaria Intl Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to San José Juan Santamaria Intl Airport.
What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?
The required travel and health documents for your San José Juan Santamaria Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at San José Juan Santamaria Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular airline from Winnipeg to San José?
Based on momondo bookings for flights between Winnipeg and San José, the leading airline is Air Canada, making up 82% of the total bookings. Other popular airlines include United Airlines with 18%.

Best airlines flying from Winnipeg to San José

Compare and see reviews for airlines that fly from Winnipeg to San José with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom C$ 674	Free Cancellation	Rating 7.4 10,123 reviews		Search United Airlines flights
Air Canada	PriceFrom C$ 823	Free Cancellation	Rating 7.1 11,540 reviews		Search Air Canada flights

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Alajuela

San Gerardo de Dota

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Why should I use momondo to find a flight deal from Winnipeg to San José?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Winnipeg to San José. momondo saves you time and could save you money on your trip.

Can I find flights from Winnipeg to San José with flexible booking policies on momondo?

Yes. All flights to San José from Winnipeg on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Winnipeg to San José?

momondo provides multiple filters to help you find the best flight to San José from Winnipeg. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Winnipeg to San José right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Winnipeg to San José flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Cheap flights from Winnipeg to San José from C$ 376

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to San José departing on 24/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Air Canada flights from Winnipeg to San José

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Avianca flights from Winnipeg to San José

Our best Avianca deals on Winnipeg to San José flight tickets

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How to get the cheapest flight ticket from Winnipeg to San José

What is the cheapest month to fly to San José?

Can stopping save me money on Winnipeg to San José flights?

What is the cheapest airline that flies from Winnipeg to San José Juan Santamaria Intl?

When to book flights from Winnipeg to San José

Cheap Winnipeg to San José (YWG to SJO) flight deals and tips

Best price found

Fastest flight time

Direct flights

Frequently asked questions about flying from Winnipeg to San José

Best airlines flying from Winnipeg to San José

Compare and see reviews for airlines that fly from Winnipeg to San José with momondo

Travelling to a place near San José?

Why use momondo?

An easier way to manage your San José trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Costa Rica

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