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 September 2026, there is 1 operator 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$ 365 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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One-way

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12:45 p.m. - 10:30 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

10h 45m1 stop Toronto Pearson Intl

8:45 a.m. - 9:14 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

12h 29m1 stop Toronto Pearson Intl

C$ 698Air Canada

Tue, 27 Oct - Sun, 1 Nov

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

16h 15m1 stop Toronto Pearson Intl

8:45 a.m. - 10:05 a.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

25h 20m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

C$ 703Air Canada

Tue, 27 Oct - Sun, 1 Nov

7:15 a.m. - 10:50 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

16h 35m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

8:45 a.m. - 10:05 a.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

25h 20m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

C$ 707Air Canada

Tue, 27 Oct - Sun, 1 Nov

6:55 p.m. - 10:30 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

27h 35m1 stop Toronto Pearson Intl

8:45 a.m. - 7:09 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

10h 24m1 stop Toronto Pearson Intl

C$ 722Air Canada

Sun, 8 Nov - Tue, 17 Nov

6:55 p.m. - 10:30 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

27h 35m1 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$ 727Air Canada

Sun, 8 Nov - Tue, 17 Nov

6:00 a.m. - 10:30 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

40h 30m2 stops Ottawa Toronto Pearson Intl

8:45 a.m. - 9:24 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

12h 39m1 stop Toronto Pearson Intl

C$ 728Air Canada

Mon, 1 Feb - Sun, 7 Feb

3:05 p.m. - 10:30 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

31h 25m1 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$ 728Air Canada

Mon, 1 Feb - Sun, 7 Feb

11:05 a.m. - 10:30 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

11h 25m1 stop Toronto Pearson Intl

8:45 a.m. - 6:25 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

33h 40m2 stops Toronto Pearson Intl Ottawa

C$ 728Air Canada

Mon, 1 Feb - Sun, 7 Feb

7:00 a.m. - 8:39 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

37h 39m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

8:45 a.m. - 10:33 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

13h 48m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

C$ 736United Airlines

Sun, 10 Jan - Fri, 29 Jan

7:00 a.m. - 8:39 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

37h 39m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

1:15 a.m. - 10:33 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

21h 18m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

C$ 736United Airlines

Sun, 17 Jan - Tue, 26 Jan

Cheap last-minute flights

Enter your travel dates to find the best prices.

2:00 p.m. - 7:37 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

30h 37m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

7:55 a.m. - 12:37 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

27h 42m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

C$ 982United Airlines

Wed, 16 Sep - Mon, 28 Sep

7:10 p.m. - 11:45 a.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

41h 35m3 stops Toronto Pearson Intl San Salvador El Salvador Intl Panama City Tocumen Intl

5:05 a.m. - 11:27 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

17h 22m2 stops San Salvador El Salvador Intl Toronto Pearson Intl

C$ 1,082Avianca

Wed, 16 Sep - Mon, 28 Sep

8:15 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

5:05 a.m. - 9:27 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

15h 22m2 stops San Salvador El Salvador Intl Toronto Pearson Intl

C$ 1,281Avianca

Wed, 16 Sep - Thu, 17 Sep

12:20 p.m. - 11:45 a.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

24h 25m3 stops Toronto Pearson Intl San Salvador El Salvador Intl Panama City Tocumen Intl

7:45 p.m. - 11:17 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

26h 32m2 stops San Salvador El Salvador Intl Toronto Pearson Intl

C$ 1,319Avianca

Wed, 16 Sep - Thu, 17 Sep

9:05 p.m. - 11:40 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

27h 35m3 stops Calgary Toronto Pearson Intl San Salvador El Salvador Intl

5:05 a.m. - 9:20 a.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

27h 15m3 stops San Salvador El Salvador Intl Toronto Pearson Intl Edmonton

C$ 1,426Multiple Airlines

Wed, 16 Sep - Mon, 28 Sep

7:10 p.m. - 10:00 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

27h 50m1 stop Toronto Pearson Intl

4:00 p.m. - 9:59 a.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

40h 59m2 stops Bogotá El Dorado Montreal Pierre Elliott Trudeau Intl

C$ 1,540Multiple Airlines

Wed, 16 Sep - Mon, 28 Sep

6:00 a.m. - 11:40 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

18h 40m3 stops Calgary Toronto Pearson Intl San Salvador El Salvador Intl

5:05 a.m. - 3:25 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

33h 20m3 stops San Salvador El Salvador Intl Toronto Pearson Intl Calgary

C$ 2,087Multiple Airlines

Wed, 16 Sep - Thu, 17 Sep

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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

27 Oct

YWG12:45 p.m.Winnipeg

10h 45m

1 stop

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

1 Nov

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

12h 29m

1 stop

YWG9:14 p.m.Winnipeg

C$ 698

Air Canada

27 Oct

YWG7:15 a.m.Winnipeg

16h 15m

1 stop

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

1 Nov

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

25h 20m

2 stops

YWG10:05 a.m.Winnipeg

C$ 703

Air Canada

27 Oct

YWG7:15 a.m.Winnipeg

16h 35m

2 stops

SJO10:50 p.m.San José Juan Santamaria Intl

1 Nov

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

25h 20m

2 stops

YWG10:05 a.m.Winnipeg

C$ 707

United Airlines flights from Winnipeg to San José

Our best United Airlines deals on Winnipeg to San José flight tickets

United Airlines

17 Jan

YWG7:00 a.m.Winnipeg

37h 39m

2 stops

SJO8:39 p.m.San José Juan Santamaria Intl

26 Jan

SJO1:15 a.m.San José Juan Santamaria Intl

21h 18m

2 stops

YWG10:33 p.m.Winnipeg

C$ 736

United Airlines

12 Jan

YWG7:00 a.m.Winnipeg

37h 39m

2 stops

SJO8:39 p.m.San José Juan Santamaria Intl

1 Feb

SJO1:15 a.m.San José Juan Santamaria Intl

21h 18m

2 stops

YWG10:33 p.m.Winnipeg

C$ 739

United Airlines

16 Jan

YWG7:00 a.m.Winnipeg

29h 15m

1 stop

SJO12:15 p.m.San José Juan Santamaria Intl

27 Jan

SJO1:15 a.m.San José Juan Santamaria Intl

21h 18m

2 stops

YWG10:33 p.m.Winnipeg

C$ 772

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

Tue 27/10

12:45 p.m.-10:30 p.m.

1 stop10h 45m

San José Juan Santamaria Intl

Sun 1/11

8:45 a.m.-9:14 p.m.

1 stop12h 29m

C$ 698

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Tue 27/10

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

1 stop16h 15m

San José Juan Santamaria Intl

Sun 1/11

8:45 a.m.-10:05 a.m.

2 stops25h 20m

C$ 703

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Tue 27/10

7:15 a.m.-10:50 p.m.

2 stops16h 35m

San José Juan Santamaria Intl

Sun 1/11

8:45 a.m.-10:05 a.m.

2 stops25h 20m

C$ 707

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 8/11

6:55 p.m.-10:30 p.m.

1 stop27h 35m

San José Juan Santamaria Intl

Tue 17/11

8:45 a.m.-7:09 p.m.

1 stop10h 24m

C$ 722

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 8/11

6:55 p.m.-10:30 p.m.

1 stop27h 35m

San José Juan Santamaria Intl

Tue 17/11

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

2 stops25h 15m

C$ 727

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 1/2

6:00 a.m.-10:30 p.m.

2 stops40h 30m

San José Juan Santamaria Intl

Sun 7/2

8:45 a.m.-9:24 p.m.

1 stop12h 39m

C$ 728

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 1/2

3:05 p.m.-10:30 p.m.

1 stop31h 25m

San José Juan Santamaria Intl

Sun 7/2

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

1 stop15h 39m

C$ 728

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 1/2

11:05 a.m.-10:30 p.m.

1 stop11h 25m

San José Juan Santamaria Intl

Sun 7/2

8:45 a.m.-6:25 p.m.

2 stops33h 40m

C$ 728

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 10/1

7:00 a.m.-8:39 p.m.

2 stops37h 39m

San José Juan Santamaria Intl

Fri 29/1

8:45 a.m.-10:33 p.m.

2 stops13h 48m

C$ 736

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 17/1

7:00 a.m.-8:39 p.m.

2 stops37h 39m

San José Juan Santamaria Intl

Tue 26/1

1:15 a.m.-10:33 p.m.

2 stops21h 18m

C$ 736

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$ 767.

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$ 365
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$ 365. The best round-trip flight deal from Winnipeg to San José found on momondo in the last 72 hours is C$ 698.

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 September 2026, there is 1 operator 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 100% of the total bookings.

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
Air Canada	PriceFrom C$ 818	Free Cancellation	Rating 7.1 11,604 reviews		Search Air Canada flights

Manuel Antonio

Jacó

Monteverde

Dominical

Santa Elena

Heredia

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$ 365

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 5/12. 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

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

United Airlines flights from Winnipeg to San José

Our best United Airlines 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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