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

United Airlines is the most popular carrier 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$ 423 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

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One-way

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2:15 p.m. - 10:32 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

32h 17m2 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$ 787United Airlines

Mon, 28 Dec - Tue, 12 Jan

7:00 a.m. - 10:25 a.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

28h 25m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

1:25 p.m. - 1:23 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

22h 58m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

C$ 796United Airlines

Sat, 24 Oct - Sat, 31 Oct

7:00 a.m. - 12:22 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

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

1:05 p.m. - 1:23 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

23h 18m1 stop Chicago O'Hare Intl

C$ 796United Airlines

Sat, 24 Oct - Sat, 31 Oct

8:40 a.m. - 7:39 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

35h 59m2 stops Denver Intl Houston George Bush Intcntl

7:30 a.m. - 12:23 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

52h 53m2 stops Denver Intl Chicago O'Hare Intl

C$ 797United Airlines

Sun, 25 Oct - Sun, 1 Nov

8:40 a.m. - 11:25 a.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

26h 45m2 stops Denver Intl Houston George Bush Intcntl

8:45 a.m. - 8:55 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

36h 10m2 stops Houston George Bush Intcntl Denver Intl

C$ 803United Airlines

Sun, 29 Nov - Thu, 3 Dec

8:40 a.m. - 11:25 a.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

26h 45m2 stops Denver Intl Houston George Bush Intcntl

8:45 a.m. - 8:55 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

36h 10m2 stops Houston George Bush Intcntl Denver Intl

C$ 804United Airlines

Sun, 29 Nov - Thu, 3 Dec

8:40 a.m. - 11:25 a.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

26h 45m2 stops Denver Intl Houston George Bush Intcntl

8:45 a.m. - 8:55 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

36h 10m2 stops Houston George Bush Intcntl Denver Intl

C$ 806United Airlines

Sun, 29 Nov - Thu, 3 Dec

2:15 p.m. - 11:25 a.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

21h 10m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

12:35 p.m. - 12:23 p.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

23h 48m2 stops Houston George Bush Intcntl Chicago O'Hare Intl

C$ 816United Airlines

Sat, 7 Nov - Mon, 16 Nov

4:10 p.m. - 10:50 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

31h 40m1 stop Montreal Pierre Elliott Trudeau Intl

7:45 a.m. - 11:24 a.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

26h 39m1 stop Toronto Pearson Intl

C$ 888Air Canada

Sat, 24 Oct - Sat, 31 Oct

11:20 a.m. - 10:30 p.m.YWG Winnipeg-SJO San José Juan Santamaria Intl

11h 10m1 stop Toronto Pearson Intl

5:35 a.m. - 10:00 a.m.SJO San José Juan Santamaria Intl-YWG Winnipeg

28h 25m2 stops Guatemala City La Aurora Montreal Pierre Elliott Trudeau Intl

C$ 925Air Canada

Mon, 9 Nov - Tue, 24 Nov

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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

28 Dec

YWG2:15 p.m.Winnipeg

32h 17m

2 stops

SJO10:32 p.m.San José Juan Santamaria Intl

12 Jan

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

21h 18m

2 stops

YWG10:33 p.m.Winnipeg

C$ 787

United Airlines

24 Oct

YWG7:00 a.m.Winnipeg

30h 22m

2 stops

SJO12:22 p.m.San José Juan Santamaria Intl

31 Oct

SJO1:05 p.m.San José Juan Santamaria Intl

23h 18m

1 stop

YWG1:23 p.m.Winnipeg

C$ 796

United Airlines

25 Oct

YWG8:40 a.m.Winnipeg

35h 59m

2 stops

SJO7:39 p.m.San José Juan Santamaria Intl

1 Nov

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

52h 53m

2 stops

YWG12:23 p.m.Winnipeg

C$ 797

Avianca flights from Winnipeg to San José

Our best Avianca deals on Winnipeg to San José flight tickets

Avianca

9 Nov

YWG7:15 a.m.Winnipeg

16h 25m

2 stops

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

24 Nov

SJO5:10 a.m.San José Juan Santamaria Intl

16h 04m

2 stops

YWG9:14 p.m.Winnipeg

C$ 857

Avianca

1 Feb

YWG11:05 a.m.Winnipeg

12h 35m

2 stops

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

8 Feb

SJO5:10 a.m.San José Juan Santamaria Intl

16h 14m

2 stops

YWG9:24 p.m.Winnipeg

C$ 894

Avianca

9 Nov

YWG5:15 a.m.Winnipeg

30h 30m

3 stops

SJO11:45 a.m.San José Juan Santamaria Intl

24 Nov

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

45h 44m

3 stops

YWG10:24 a.m.Winnipeg

C$ 959

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 28/12

2:15 p.m.-10:32 p.m.

2 stops32h 17m

San José Juan Santamaria Intl

Tue 12/1

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

2 stops21h 18m

C$ 787

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sat 24/10

7:00 a.m.-10:25 a.m.

2 stops28h 25m

San José Juan Santamaria Intl

Sat 31/10

1:25 p.m.-1:23 p.m.

2 stops22h 58m

C$ 796

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sat 24/10

7:00 a.m.-12:22 p.m.

2 stops30h 22m

San José Juan Santamaria Intl

Sat 31/10

1:05 p.m.-1:23 p.m.

1 stop23h 18m

C$ 796

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 25/10

8:40 a.m.-7:39 p.m.

2 stops35h 59m

San José Juan Santamaria Intl

Sun 1/11

7:30 a.m.-12:23 p.m.

2 stops52h 53m

C$ 797

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 29/11

8:40 a.m.-11:25 a.m.

2 stops26h 45m

San José Juan Santamaria Intl

Thu 3/12

8:45 a.m.-8:55 p.m.

2 stops36h 10m

C$ 803

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 29/11

8:40 a.m.-11:25 a.m.

2 stops26h 45m

San José Juan Santamaria Intl

Thu 3/12

8:45 a.m.-8:55 p.m.

2 stops36h 10m

C$ 804

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 29/11

8:40 a.m.-11:25 a.m.

2 stops26h 45m

San José Juan Santamaria Intl

Thu 3/12

8:45 a.m.-8:55 p.m.

2 stops36h 10m

C$ 806

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sat 7/11

2:15 p.m.-11:25 a.m.

2 stops21h 10m

San José Juan Santamaria Intl

Mon 16/11

12:35 p.m.-12:23 p.m.

2 stops23h 48m

C$ 816

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sat 24/10

4:10 p.m.-10:50 p.m.

1 stop31h 40m

San José Juan Santamaria Intl

Sat 31/10

7:45 a.m.-11:24 a.m.

1 stop26h 39m

C$ 888

Quickest round-trip

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 9/11

11:20 a.m.-10:30 p.m.

1 stop11h 10m

San José Juan Santamaria Intl

Tue 24/11

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

2 stops28h 25m

C$ 925

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$ 799.

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$ 423
Fastest flight time	11h 55m
Direct flights	None

The best one-way flight to San José from Winnipeg in the past 72 hours is C$ 423. The best round-trip flight deal from Winnipeg to San José found on momondo in the last 72 hours is C$ 787.

The fastest flight from Winnipeg to San José takes 11h 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. 11h 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$ 840	Free Cancellation	Rating 7.1 11,701 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?

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Cheap flights from Winnipeg to San José from C$ 423

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 1/2. 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

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

Airports servicing Costa Rica

Fly your favourite airline to San José

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