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Cheap flights from Winnipeg to San José from C$ 367

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 14/6. 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

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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
3:15 p.m. - 10:00 p.m.
YWG
-
SJO
31h 45m
1 stop
Air Canada Logo
7:10 a.m. - 11:15 a.m.
SJO
-
YWG
27h 05m
1 stop
C$ 703Air Canada
Sun, 14 Jun - Tue, 23 Jun
Air Canada Logo
7:20 p.m. - 8:35 p.m.
YWG
-
SJO
50h 15m
2 stops
Air Canada Logo
7:10 a.m. - 11:15 a.m.
SJO
-
YWG
27h 05m
1 stop
C$ 708Air Canada
Fri, 12 Jun - Tue, 23 Jun
Air Canada Logo
5:10 p.m. - 10:00 p.m.
YWG
-
SJO
29h 50m
1 stop
Air Canada Logo
7:15 a.m. - 8:01 p.m.
SJO
-
YWG
35h 46m
2 stops
C$ 766Air Canada
Sun, 14 Jun - Mon, 22 Jun
Air Canada Logo
7:20 p.m. - 8:35 p.m.
YWG
-
SJO
26h 15m
2 stops
Air Canada Logo
7:15 a.m. - 8:01 p.m.
SJO
-
YWG
35h 46m
2 stops
C$ 770Air Canada
Sat, 13 Jun - Mon, 22 Jun
Air Canada Logo
7:20 p.m. - 10:00 p.m.
YWG
-
SJO
27h 40m
1 stop
Air Canada Logo
7:10 a.m. - 11:15 a.m.
SJO
-
YWG
27h 05m
1 stop
C$ 773Air Canada
Fri, 12 Jun - Tue, 23 Jun
United Airlines Logo
8:45 a.m. - 10:11 a.m.
YWG
-
SJO
26h 26m
2 stops
United Airlines Logo
1:25 p.m. - 11:52 a.m.
SJO
-
YWG
45h 27m
2 stops
C$ 811United Airlines
Mon, 20 Apr - Sun, 26 Apr
Air Canada Logo
4:05 p.m. - 8:35 p.m.
YWG
-
SJO
29h 30m
1 stop
Air Canada Logo
7:10 a.m. - 11:15 a.m.
SJO
-
YWG
27h 05m
1 stop
C$ 829Air Canada
Sat, 13 Jun - Tue, 23 Jun
Air Canada Logo
7:20 p.m. - 8:35 p.m.
YWG
-
SJO
26h 15m
2 stops
Air Canada Logo
7:15 a.m. - 10:05 a.m.
SJO
-
YWG
25h 50m
1 stop
C$ 831Air Canada
Sat, 13 Jun - Mon, 22 Jun
Air Canada Logo
7:20 p.m. - 8:35 p.m.
YWG
-
SJO
50h 15m
2 stops
Air Canada Logo
7:15 a.m. - 10:05 a.m.
SJO
-
YWG
25h 50m
1 stop
C$ 834Air Canada
Fri, 12 Jun - Mon, 22 Jun
United Airlines Logo
7:00 a.m. - 7:37 p.m.
YWG
-
SJO
37h 37m
2 stops
United Airlines Logo
12:30 a.m. - 8:57 p.m.
SJO
-
YWG
19h 27m
2 stops
C$ 836United Airlines
Fri, 12 Jun - Mon, 22 Jun

Air Canada flights from Winnipeg to San José

Our best Air Canada deals on Winnipeg to San José flight tickets
Air Canada
14 Jun
YWG3:15 p.m.Winnipeg
31h 45m
1 stop
SJO10:00 p.m.San José Juan Santamaria Intl
23 Jun
SJO7:10 a.m.San José Juan Santamaria Intl
27h 05m
1 stop
YWG11:15 a.m.Winnipeg
C$ 703
Air Canada
12 Jun
YWG7:20 p.m.Winnipeg
50h 15m
2 stops
SJO8:35 p.m.San José Juan Santamaria Intl
23 Jun
SJO7:10 a.m.San José Juan Santamaria Intl
27h 05m
1 stop
YWG11:15 a.m.Winnipeg
C$ 708
Air Canada
14 Jun
YWG5:10 p.m.Winnipeg
29h 50m
1 stop
SJO10:00 p.m.San José Juan Santamaria Intl
22 Jun
SJO7:15 a.m.San José Juan Santamaria Intl
35h 46m
2 stops
YWG8:01 p.m.Winnipeg
C$ 766

United Airlines flights from Winnipeg to San José

Our best United Airlines deals on Winnipeg to San José flight tickets
United Airlines
11 Apr
YWG2:00 p.m.Winnipeg
23h 21m
2 stops
SJO12:21 p.m.San José Juan Santamaria Intl
18 Apr
SJO6:00 a.m.San José Juan Santamaria Intl
37h 57m
2 stops
YWG8:57 p.m.Winnipeg
C$ 752
United Airlines
11 Apr
YWG2:00 p.m.Winnipeg
21h 11m
2 stops
SJO10:11 a.m.San José Juan Santamaria Intl
18 Apr
SJO1:00 p.m.San José Juan Santamaria Intl
21h 52m
1 stop
YWG11:52 a.m.Winnipeg
C$ 811
United Airlines
12 Jun
YWG7:00 a.m.Winnipeg
37h 37m
2 stops
SJO7:37 p.m.San José Juan Santamaria Intl
22 Jun
SJO12:30 a.m.San José Juan Santamaria Intl
19h 27m
2 stops
YWG8:57 p.m.Winnipeg
C$ 836

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 9 April 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 - SJO

YWGSJO

Winnipeg

Sun 14/6

3:15 p.m.-10:00 p.m.

1 stop31h 45m

San José Juan Santamaria Intl

Tue 23/6

7:10 a.m.-11:15 a.m.

1 stop27h 05m

C$ 703

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 12/6

7:20 p.m.-8:35 p.m.

2 stops50h 15m

San José Juan Santamaria Intl

Tue 23/6

7:10 a.m.-11:15 a.m.

1 stop27h 05m

C$ 708

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 14/6

5:10 p.m.-10:00 p.m.

1 stop29h 50m

San José Juan Santamaria Intl

Mon 22/6

7:15 a.m.-8:01 p.m.

2 stops35h 46m

C$ 766

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 13/6

7:20 p.m.-8:35 p.m.

2 stops26h 15m

San José Juan Santamaria Intl

Mon 22/6

7:15 a.m.-8:01 p.m.

2 stops35h 46m

C$ 770

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 12/6

7:20 p.m.-10:00 p.m.

1 stop27h 40m

San José Juan Santamaria Intl

Tue 23/6

7:10 a.m.-11:15 a.m.

1 stop27h 05m

C$ 773

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 20/4

8:45 a.m.-10:11 a.m.

2 stops26h 26m

San José Juan Santamaria Intl

Sun 26/4

1:25 p.m.-11:52 a.m.

2 stops45h 27m

C$ 811

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 13/6

4:05 p.m.-8:35 p.m.

1 stop29h 30m

San José Juan Santamaria Intl

Tue 23/6

7:10 a.m.-11:15 a.m.

1 stop27h 05m

C$ 829
Quickest round-trip

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 13/6

7:20 p.m.-8:35 p.m.

2 stops26h 15m

San José Juan Santamaria Intl

Mon 22/6

7:15 a.m.-10:05 a.m.

1 stop25h 50m

C$ 831

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 12/6

7:20 p.m.-8:35 p.m.

2 stops50h 15m

San José Juan Santamaria Intl

Mon 22/6

7:15 a.m.-10:05 a.m.

1 stop25h 50m

C$ 834

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 12/6

7:00 a.m.-7:37 p.m.

2 stops37h 37m

San José Juan Santamaria Intl

Mon 22/6

12:30 a.m.-8:57 p.m.

2 stops19h 27m

C$ 836

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

What is the cheapest month to fly to San José?

In general, July 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$ 820. If you aren’t able to travel during the month of July, then book flights to San José from Winnipeg during October instead. Flights to San José in October, while not as cheap as those in July, still average around C$ 850.

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

14h 54m

Direct flights

None
The fastest flight from Winnipeg to San José takes 14h 54m
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. 14h 54m 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$ 673Free CancellationRating
7.4
9,555 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 997Free CancellationRating
7.1
10,907 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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