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Cheap flights from Winnipeg to San José from C$ 388

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 15/6. 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

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
5:10 a.m. - 11:40 p.m.
YWG
-
SJO
19h 30m
2 stops
Air Canada Logo
7:35 a.m. - 6:29 p.m.
SJO
-
YWG
9h 54m
1 stop
C$ 742Air Canada
Wed, 21 Oct - Wed, 28 Oct
Air Canada Logo
5:10 a.m. - 11:40 p.m.
YWG
-
SJO
19h 30m
2 stops
Air Canada Logo
7:10 a.m. - 11:12 a.m.
SJO
-
YWG
27h 02m
1 stop
C$ 746Air Canada
Tue, 29 Sep - Fri, 2 Oct
Air Canada Logo
2:00 p.m. - 10:00 p.m.
YWG
-
SJO
9h 00m
1 stop
Air Canada Logo
7:10 a.m. - 10:09 a.m.
SJO
-
YWG
25h 59m
2 stops
C$ 748Air Canada
Mon, 1 Jun - Tue, 2 Jun
Air Canada Logo
5:10 a.m. - 11:40 p.m.
YWG
-
SJO
19h 30m
2 stops
Air Canada Logo
7:10 a.m. - 11:07 p.m.
SJO
-
YWG
14h 57m
1 stop
C$ 749Air Canada
Tue, 29 Sep - Fri, 2 Oct
Air Canada Logo
8:15 a.m. - 11:40 p.m.
YWG
-
SJO
16h 25m
2 stops
Air Canada Logo
7:10 a.m. - 8:00 p.m.
SJO
-
YWG
35h 50m
2 stops
C$ 750Air Canada
Tue, 29 Sep - Fri, 2 Oct
Air Canada Logo
5:10 a.m. - 11:40 p.m.
YWG
-
SJO
19h 30m
2 stops
Air Canada Logo
5:05 a.m. - 11:12 a.m.
SJO
-
YWG
29h 07m
2 stops
C$ 752Air Canada
Tue, 29 Sep - Fri, 2 Oct
Air Canada Logo
3:20 p.m. - 10:00 p.m.
YWG
-
SJO
31h 40m
1 stop
Air Canada Logo
7:35 a.m. - 10:39 p.m.
SJO
-
YWG
14h 04m
1 stop
C$ 782Air Canada
Wed, 21 Oct - Wed, 28 Oct
Air Canada Logo
8:15 a.m. - 11:40 p.m.
YWG
-
SJO
16h 25m
2 stops
Air Canada Logo
7:10 a.m. - 11:12 a.m.
SJO
-
YWG
27h 02m
1 stop
C$ 797Air Canada
Tue, 29 Sep - Fri, 2 Oct
Air Canada Logo
8:15 a.m. - 11:40 p.m.
YWG
-
SJO
16h 25m
2 stops
Air Canada Logo
5:05 a.m. - 4:17 p.m.
SJO
-
YWG
34h 12m
2 stops
C$ 798Air Canada
Tue, 29 Sep - Fri, 2 Oct
Avianca Logo
12:15 p.m. - 10:00 p.m.
YWG
-
SJO
10h 45m
1 stop
Avianca Logo
5:05 a.m. - 11:08 a.m.
SJO
-
YWG
29h 03m
2 stops
C$ 828Avianca
Mon, 8 Jun - Tue, 9 Jun

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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
21 Oct
YWG5:10 a.m.Winnipeg
19h 30m
2 stops
SJO11:40 p.m.San José Juan Santamaria Intl
28 Oct
SJO7:35 a.m.San José Juan Santamaria Intl
9h 54m
1 stop
YWG6:29 p.m.Winnipeg
C$ 742
Air Canada
29 Sep
YWG5:10 a.m.Winnipeg
19h 30m
2 stops
SJO11:40 p.m.San José Juan Santamaria Intl
2 Oct
SJO7:10 a.m.San José Juan Santamaria Intl
27h 02m
1 stop
YWG11:12 a.m.Winnipeg
C$ 746
Air Canada
1 Jun
YWG2:00 p.m.Winnipeg
9h 00m
1 stop
SJO10:00 p.m.San José Juan Santamaria Intl
2 Jun
SJO7:10 a.m.San José Juan Santamaria Intl
25h 59m
2 stops
YWG10:09 a.m.Winnipeg
C$ 748

Avianca flights from Winnipeg to San José

Our best Avianca deals on Winnipeg to San José flight tickets
Avianca
8 Jun
YWG12:15 p.m.Winnipeg
10h 45m
1 stop
SJO10:00 p.m.San José Juan Santamaria Intl
9 Jun
SJO5:05 a.m.San José Juan Santamaria Intl
29h 03m
2 stops
YWG11:08 a.m.Winnipeg
C$ 828
Avianca
21 Oct
YWG12:20 p.m.Winnipeg
24h 25m
3 stops
SJO11:45 a.m.San José Juan Santamaria Intl
28 Oct
SJO7:50 p.m.San José Juan Santamaria Intl
21h 39m
2 stops
YWG6:29 p.m.Winnipeg
C$ 997
Avianca
21 Oct
YWG8:15 a.m.Winnipeg
28h 30m
3 stops
SJO11:45 a.m.San José Juan Santamaria Intl
28 Oct
SJO12:40 p.m.San José Juan Santamaria Intl
28h 49m
3 stops
YWG6:29 p.m.Winnipeg
C$ 1,047

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 5 May 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
Quickest round-trip

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 21/10

5:10 a.m.-11:40 p.m.

2 stops19h 30m

San José Juan Santamaria Intl

Wed 28/10

7:35 a.m.-6:29 p.m.

1 stop9h 54m

C$ 742

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 29/9

5:10 a.m.-11:40 p.m.

2 stops19h 30m

San José Juan Santamaria Intl

Fri 2/10

7:10 a.m.-11:12 a.m.

1 stop27h 02m

C$ 746

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 1/6

2:00 p.m.-10:00 p.m.

1 stop9h 00m

San José Juan Santamaria Intl

Tue 2/6

7:10 a.m.-10:09 a.m.

2 stops25h 59m

C$ 748

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 29/9

5:10 a.m.-11:40 p.m.

2 stops19h 30m

San José Juan Santamaria Intl

Fri 2/10

7:10 a.m.-11:07 p.m.

1 stop14h 57m

C$ 749

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 29/9

8:15 a.m.-11:40 p.m.

2 stops16h 25m

San José Juan Santamaria Intl

Fri 2/10

7:10 a.m.-8:00 p.m.

2 stops35h 50m

C$ 750

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 29/9

5:10 a.m.-11:40 p.m.

2 stops19h 30m

San José Juan Santamaria Intl

Fri 2/10

5:05 a.m.-11:12 a.m.

2 stops29h 07m

C$ 752

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 21/10

3:20 p.m.-10:00 p.m.

1 stop31h 40m

San José Juan Santamaria Intl

Wed 28/10

7:35 a.m.-10:39 p.m.

1 stop14h 04m

C$ 782

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 29/9

8:15 a.m.-11:40 p.m.

2 stops16h 25m

San José Juan Santamaria Intl

Fri 2/10

7:10 a.m.-11:12 a.m.

1 stop27h 02m

C$ 797

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 29/9

8:15 a.m.-11:40 p.m.

2 stops16h 25m

San José Juan Santamaria Intl

Fri 2/10

5:05 a.m.-4:17 p.m.

2 stops34h 12m

C$ 798

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 8/6

12:15 p.m.-10:00 p.m.

1 stop10h 45m

San José Juan Santamaria Intl

Tue 9/6

5:05 a.m.-11:08 a.m.

2 stops29h 03m

C$ 828

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first
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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 typical price of a round-trip flight between Winnipeg and San José?

What is the cheapest month to fly to San José?

In general, April 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$ 768. If you aren’t able to travel during the month of April, then book flights to San José from Winnipeg during July instead. Flights to San José in July, while not as cheap as those in April, still average around C$ 806.

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

Fastest flight time

26h 26m

Direct flights

None
The fastest flight from Winnipeg to San José takes 26h 26m
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 26m 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$ 662Free CancellationRating
7.4
9,683 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 969Free CancellationRating
7.1
10,998 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
Jacó
Manuel Antonio
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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