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Cheap flights from Winnipeg to San José from C$ 381

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 25/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Winnipeg to San José

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
8:05 a.m. - 11:50 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
15h 45m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
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$ 672Air Canada
Sun, 10 Jan - Sun, 17 Jan
Air Canada Logo
6:00 a.m. - 10:30 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
16h 30m2 stops Ottawa Toronto Pearson Intl
Air Canada Logo
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$ 679Air Canada
Sun, 10 Jan - Sun, 17 Jan
Air Canada Logo
12:45 p.m. - 10:30 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
9h 45m1 stop Toronto Pearson Intl
Air Canada Logo
9:20 a.m. - 10:00 a.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
24h 40m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 690Air Canada
Wed, 9 Dec - Wed, 10 Feb
Air Canada Logo
6:00 a.m. - 10:30 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
16h 30m2 stops Ottawa Toronto Pearson Intl
Air Canada Logo
9:20 a.m. - 10:00 a.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
24h 40m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 690Air Canada
Wed, 9 Dec - Wed, 10 Feb
Multiple Airlines Logo
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
Multiple Airlines Logo
5:00 a.m. - 7:09 p.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
14h 09m2 stops San Salvador El Salvador Intl Toronto Pearson Intl
C$ 717Multiple Airlines
Mon, 1 Feb - Mon, 8 Feb
United Airlines Logo
2:15 p.m. - 12:15 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
22h 00m1 stop Chicago O'Hare Intl
United Airlines Logo
1:05 p.m. - 11:39 a.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
21h 34m1 stop Chicago O'Hare Intl
C$ 739United Airlines
Tue, 2 Feb - Tue, 16 Mar
United Airlines Logo
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
United Airlines Logo
7:45 a.m. - 11:39 a.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
26h 54m2 stops Houston George Bush Intcntl Chicago O'Hare Intl
C$ 739United Airlines
Tue, 2 Feb - Tue, 16 Mar
United Airlines Logo
2:15 p.m. - 6:16 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
28h 01m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
United Airlines Logo
2:05 p.m. - 11:39 a.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
21h 34m1 stop Chicago O'Hare Intl
C$ 739United Airlines
Sun, 14 Feb - Thu, 11 Mar
Avianca Logo
11:05 a.m. - 11:40 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
12h 35m2 stops Toronto Pearson Intl San Salvador El Salvador Intl
Avianca Logo
5:00 a.m. - 10:09 a.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
29h 09m2 stops San Salvador El Salvador Intl Toronto Pearson Intl
C$ 774Avianca
Mon, 1 Feb - Sun, 7 Feb
Avianca Logo
11:05 a.m. - 11:40 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
12h 35m2 stops Toronto Pearson Intl San Salvador El Salvador Intl
Avianca Logo
5:00 a.m. - 10:09 a.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
29h 09m2 stops San Salvador El Salvador Intl Toronto Pearson Intl
C$ 776Avianca
Mon, 1 Feb - Sun, 7 Feb

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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
10 Jan
YWG8:05 a.m.Winnipeg
15h 45m
1 stop
SJO11:50 p.m.San José Juan Santamaria Intl
17 Jan
SJO8:45 a.m.San José Juan Santamaria Intl
25h 15m
2 stops
YWG10:00 a.m.Winnipeg
C$ 672
Air Canada
10 Jan
YWG6:00 a.m.Winnipeg
16h 30m
2 stops
SJO10:30 p.m.San José Juan Santamaria Intl
17 Jan
SJO8:45 a.m.San José Juan Santamaria Intl
25h 15m
2 stops
YWG10:00 a.m.Winnipeg
C$ 679
Air Canada
9 Dec
YWG12:45 p.m.Winnipeg
9h 45m
1 stop
SJO10:30 p.m.San José Juan Santamaria Intl
10 Feb
SJO9:20 a.m.San José Juan Santamaria Intl
24h 40m
1 stop
YWG10:00 a.m.Winnipeg
C$ 690

United Airlines flights from Winnipeg to San José

Our best United Airlines deals on Winnipeg to San José flight tickets
United Airlines
31 Jan
YWG2:15 p.m.Winnipeg
30h 24m
2 stops
SJO8:39 p.m.San José Juan Santamaria Intl
11 Mar
SJO2:05 p.m.San José Juan Santamaria Intl
21h 34m
1 stop
YWG11:39 a.m.Winnipeg
C$ 739
United Airlines
21 Dec
YWG2:15 p.m.Winnipeg
28h 01m
2 stops
SJO6:16 p.m.San José Juan Santamaria Intl
2 Mar
SJO12:35 p.m.San José Juan Santamaria Intl
23h 04m
2 stops
YWG11:39 a.m.Winnipeg
C$ 772
United Airlines
30 Jan
YWG2:15 p.m.Winnipeg
22h 00m
1 stop
SJO12:15 p.m.San José Juan Santamaria Intl
17 Mar
SJO7:45 a.m.San José Juan Santamaria Intl
26h 54m
2 stops
YWG11:39 a.m.Winnipeg
C$ 775

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to San José that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 18 August 2026.
Use the filters below to find and compare flights from Winnipeg to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 10/1

8:05 a.m.-11:50 p.m.

1 stop15h 45m

San José Juan Santamaria Intl

Sun 17/1

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

2 stops25h 15m

C$ 672

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 10/1

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

2 stops16h 30m

San José Juan Santamaria Intl

Sun 17/1

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

2 stops25h 15m

C$ 679

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Wed 9/12

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

1 stop9h 45m

San José Juan Santamaria Intl

Wed 10/2

9:20 a.m.-10:00 a.m.

1 stop24h 40m

C$ 690

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Wed 9/12

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

2 stops16h 30m

San José Juan Santamaria Intl

Wed 10/2

9:20 a.m.-10:00 a.m.

1 stop24h 40m

C$ 690
Quickest round-trip

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 1/2

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

2 stops16h 25m

San José Juan Santamaria Intl

Mon 8/2

5:00 a.m.-7:09 p.m.

2 stops14h 09m

C$ 717

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Tue 2/2

2:15 p.m.-12:15 p.m.

1 stop22h 00m

San José Juan Santamaria Intl

Tue 16/3

1:05 p.m.-11:39 a.m.

1 stop21h 34m

C$ 739

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Tue 2/2

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

2 stops30h 24m

San José Juan Santamaria Intl

Tue 16/3

7:45 a.m.-11:39 a.m.

2 stops26h 54m

C$ 739

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 14/2

2:15 p.m.-6:16 p.m.

2 stops28h 01m

San José Juan Santamaria Intl

Thu 11/3

2:05 p.m.-11:39 a.m.

1 stop21h 34m

C$ 739

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 1/2

11:05 a.m.-11:40 p.m.

2 stops12h 35m

San José Juan Santamaria Intl

Sun 7/2

5:00 a.m.-10:09 a.m.

2 stops29h 09m

C$ 774

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 1/2

11:05 a.m.-11:40 p.m.

2 stops12h 35m

San José Juan Santamaria Intl

Sun 7/2

5:00 a.m.-10:09 a.m.

2 stops29h 09m

C$ 776

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to San José from

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

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 10% 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$ 381

Fastest flight time

28h 36m

Direct flights

None
The best one-way flight to San José from Winnipeg in the past 72 hours is C$ 381. The best round-trip flight deal from Winnipeg to San José found on momondo in the last 72 hours is C$ 672.
The fastest flight from Winnipeg to San José takes 28h 36m
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. 28h 36m 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?

  • 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?

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 AirlinesPriceFrom C$ 674Free CancellationRating
7.4
10,102 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 822Free CancellationRating
7.1
11,497 reviews
Search Air Canada flights

Travelling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Jacó
Monteverde
Dominical
Heredia
Santa Elena
Alajuela
San Gerardo de Dota

Why use momondo?

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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