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

United Airlines and Air Canada 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 November 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$ 436 Cheap Flights from Winnipeg to San José in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Winnipeg to San José

Round-trip

One-way

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Cheap round-trip flights

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9:40 a.m. - 12:15 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

27h 35m2 stops Denver Intl Chicago O'Hare Intl

1:15 a.m. - 9:55 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

19h 40m2 stops Houston George Bush Intcntl Denver Intl

C$ 805United Airlines

Fri, 8 Jan - Mon, 8 Feb

9:40 a.m. - 12:15 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

27h 35m2 stops Denver Intl Chicago O'Hare Intl

8:45 a.m. - 7:26 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

33h 41m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

C$ 805United Airlines

Thu, 11 Feb - Sun, 21 Feb

8:00 a.m. - 1:22 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

30h 22m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

8:45 a.m. - 7:28 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

33h 43m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

C$ 805United Airlines

Wed, 6 Jan - Tue, 9 Feb

9:40 a.m. - 1:22 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

28h 42m2 stops Denver Intl Houston George Bush Intcntl

7:30 a.m. - 9:55 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

13h 25m1 stop Denver Intl

C$ 805United Airlines

Mon, 1 Feb - Sun, 7 Feb

8:00 a.m. - 1:22 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

30h 22m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

2:25 p.m. - 7:28 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

28h 03m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

C$ 805United Airlines

Tue, 5 Jan - Tue, 9 Feb

8:40 a.m. - 10:11 a.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

26h 31m2 stops Denver Intl Houston George Bush Intcntl

1:25 p.m. - 11:39 a.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

21h 14m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

C$ 805United Airlines

Tue, 13 Apr - Thu, 15 Apr

8:00 a.m. - 1:22 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

30h 22m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

1:15 a.m. - 9:55 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

19h 40m2 stops Houston George Bush Intcntl Denver Intl

C$ 805United Airlines

Thu, 7 Jan - Mon, 8 Feb

3:15 p.m. - 1:22 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

23h 07m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

1:15 a.m. - 9:55 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

19h 40m2 stops Houston George Bush Intcntl Denver Intl

C$ 805United Airlines

Mon, 4 Jan - Mon, 8 Feb

7:00 a.m. - 11:50 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

17h 50m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl

9:20 a.m. - 11:18 a.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

24h 58m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 856Air Canada

Sun, 29 Nov - Wed, 9 Dec

7:00 a.m. - 11:50 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

17h 50m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl

9:20 a.m. - 5:38 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

31h 18m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 856Air Canada

Sun, 29 Nov - Mon, 7 Dec

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United Airlines flights from Winnipeg to San José

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

United Airlines

1 Feb

YWG9:40 a.m.Winnipeg

28h 42m

2 stops

SJO1:22 p.m.San José Juan Santamaria Intl

7 Feb

SJO7:30 a.m.San José Juan Santamaria Intl

13h 25m

1 stop

YWG9:55 p.m.Winnipeg

C$ 805

United Airlines

27 Nov

YWG9:40 a.m.Winnipeg

35h 59m

2 stops

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

8 Dec

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

27h 38m

2 stops

YWG1:23 p.m.Winnipeg

C$ 808

United Airlines

27 Nov

YWG9:40 a.m.Winnipeg

21h 45m

2 stops

SJO6:25 a.m.San José Juan Santamaria Intl

7 Dec

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

27h 38m

2 stops

YWG1:23 p.m.Winnipeg

C$ 814

Air Canada flights from Winnipeg to San José

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

Air Canada

29 Nov

YWG7:00 a.m.Winnipeg

17h 50m

2 stops

SJO11:50 p.m.San José Juan Santamaria Intl

9 Dec

SJO9:20 a.m.San José Juan Santamaria Intl

24h 58m

1 stop

YWG11:18 a.m.Winnipeg

C$ 856

Air Canada

29 Nov

YWG7:00 a.m.Winnipeg

17h 50m

2 stops

SJO11:50 p.m.San José Juan Santamaria Intl

11 Dec

SJO5:35 a.m.San José Juan Santamaria Intl

28h 43m

2 stops

YWG11:18 a.m.Winnipeg

C$ 859

Air Canada

29 Nov

YWG9:05 a.m.Winnipeg

15h 45m

1 stop

SJO11:50 p.m.San José Juan Santamaria Intl

9 Dec

SJO9:20 a.m.San José Juan Santamaria Intl

24h 58m

1 stop

YWG11:18 a.m.Winnipeg

C$ 862

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Fri 8/1

9:40 a.m.-12:15 p.m.

2 stops27h 35m

San José Juan Santamaria Intl

Mon 8/2

1:15 a.m.-9:55 p.m.

2 stops19h 40m

C$ 805

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Thu 11/2

9:40 a.m.-12:15 p.m.

2 stops27h 35m

San José Juan Santamaria Intl

Sun 21/2

8:45 a.m.-7:26 p.m.

2 stops33h 41m

C$ 805

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Wed 6/1

8:00 a.m.-1:22 p.m.

2 stops30h 22m

San José Juan Santamaria Intl

Tue 9/2

8:45 a.m.-7:28 p.m.

2 stops33h 43m

C$ 805

Quickest round-trip

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 1/2

9:40 a.m.-1:22 p.m.

2 stops28h 42m

San José Juan Santamaria Intl

Sun 7/2

7:30 a.m.-9:55 p.m.

1 stop13h 25m

C$ 805

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Tue 5/1

8:00 a.m.-1:22 p.m.

2 stops30h 22m

San José Juan Santamaria Intl

Tue 9/2

2:25 p.m.-7:28 p.m.

2 stops28h 03m

C$ 805

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Tue 13/4

8:40 a.m.-10:11 a.m.

2 stops26h 31m

San José Juan Santamaria Intl

Thu 15/4

1:25 p.m.-11:39 a.m.

2 stops21h 14m

C$ 805

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Thu 7/1

8:00 a.m.-1:22 p.m.

2 stops30h 22m

San José Juan Santamaria Intl

Mon 8/2

1:15 a.m.-9:55 p.m.

2 stops19h 40m

C$ 805

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 4/1

3:15 p.m.-1:22 p.m.

2 stops23h 07m

San José Juan Santamaria Intl

Mon 8/2

1:15 a.m.-9:55 p.m.

2 stops19h 40m

C$ 805

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 29/11

7:00 a.m.-11:50 p.m.

2 stops17h 50m

San José Juan Santamaria Intl

Wed 9/12

9:20 a.m.-11:18 a.m.

1 stop24h 58m

C$ 856

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 29/11

7:00 a.m.-11:50 p.m.

2 stops17h 50m

San José Juan Santamaria Intl

Mon 7/12

9:20 a.m.-5:38 p.m.

1 stop31h 18m

C$ 856

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 typical price of a round-trip flight between Winnipeg and San José?

Prices are currently low for flights on this route.

Typical prices usually range from C$ 928 to C$ 1,329.
The lowest price recently found on this route was C$ 805.

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$ 797.

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

You could potentially save up to 19% 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$ 436
Fastest flight time	26h 31m
Direct flights	None

The best one-way flight to San José from Winnipeg in the past 72 hours is C$ 436. The best round-trip flight deal from Winnipeg to San José found on momondo in the last 72 hours is C$ 805.

The fastest flight from Winnipeg to San José takes 26h 31m

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. 26h 31m 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 November 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$ 838	Free Cancellation	Rating 7.1 11,874 reviews		Search Air Canada flights

Manuel Antonio

Jacó

Monteverde

Dominical

Santa Elena

Alajuela

Heredia

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$ 436

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 3/12. 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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United Airlines flights from Winnipeg to San José

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

Air Canada flights from Winnipeg to San José

Our best Air Canada 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 typical price of a round-trip flight between Winnipeg and 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

Airports servicing Costa Rica

Fly your favourite airline to San José

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