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Cheap flights from Winnipeg to San José from C$ 305

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 23/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Winnipeg to San José

Cheap round-trip flights

Logo
9:10 a.m. - 10:27 a.m.YWG-SJO
26h 17m1 stop
Logo
12:19 p.m. - 9:41 a.m.SJO-YWG
20h 22m2 stops
C$ 655
Find Deal
Sat, 27 Sep - Sat, 4 Oct
United Airlines Logo
2:15 p.m. - 12:56 p.m.YWG-SJO
22h 41m1 stop
United Airlines Logo
1:05 p.m. - 11:39 a.m.SJO-YWG
21h 34m1 stop
C$ 669United Airlines
Find Deal
Sun, 22 Feb - Wed, 11 Mar
United Airlines Logo
2:15 p.m. - 6:25 a.m.YWG-SJO
16h 10m2 stops
United Airlines Logo
11:35 a.m. - 11:39 a.m.SJO-YWG
23h 04m2 stops
C$ 694United Airlines
Find Deal
Sat, 28 Feb - Wed, 11 Mar
United Airlines Logo
2:15 p.m. - 12:56 p.m.YWG-SJO
22h 41m1 stop
United Airlines Logo
2:20 p.m. - 10:39 a.m.SJO-YWG
20h 19m2 stops
C$ 720United Airlines
Find Deal
Sat, 28 Feb - Sat, 7 Mar
United Airlines Logo
8:40 a.m. - 8:39 p.m.YWG-SJO
35h 59m2 stops
United Airlines Logo
8:45 a.m. - 11:57 a.m.SJO-YWG
27h 12m2 stops
C$ 743United Airlines
Find Deal
Sun, 28 Dec - Wed, 14 Jan
Logo
2:35 p.m. - 10:41 a.m.YWG-SJO
21h 06m2 stops
Logo
5:05 a.m. - 9:41 a.m.SJO-YWG
27h 36m2 stops
C$ 754
Find Deal
Sun, 5 Oct - Sun, 12 Oct
Air Transat Logo
6:00 a.m. - 11:35 p.m.YWG-SJO
17h 35m1 stop
Air Transat Logo
11:55 p.m. - 3:30 p.m.SJO-YWG
14h 35m1 stop
C$ 831Air Transat
Find Deal
Tue, 24 Feb - Thu, 12 Mar
Air Transat Logo
6:00 a.m. - 11:35 p.m.YWG-SJO
17h 35m1 stop
Air Transat Logo
11:55 p.m. - 2:30 p.m.SJO-YWG
14h 35m1 stop
C$ 896Air Transat
Find Deal
Tue, 24 Feb - Sat, 7 Mar
Air Canada Logo
1:30 p.m. - 10:55 p.m.YWG-SJO
9h 25m1 stop
Air Canada Logo
8:50 a.m. - 8:28 p.m.SJO-YWG
11h 38m2 stops
C$ 963Air Canada
Find Deal
Wed, 5 Nov - Wed, 12 Nov
Air Canada Logo
8:15 a.m. - 11:15 p.m.YWG-SJO
15h 00m1 stop
Air Canada Logo
7:35 a.m. - 7:24 p.m.SJO-YWG
10h 49m1 stop
C$ 1,055Air Canada
Find Deal
Tue, 24 Feb - Wed, 11 Mar

United Airlines flights from Winnipeg to San José, San José Province

Our best United Airlines deals on Winnipeg to San José, San José Province flight tickets
United Airlines
22 Feb
YWG2:15 p.m.Winnipeg
22h 41m
1 stop
SJO12:56 p.m.San José Juan Santamaria Intl
11 Mar
SJO1:05 p.m.San José Juan Santamaria Intl
21h 34m
1 stop
YWG11:39 a.m.Winnipeg
C$ 669
Find similar
United Airlines
28 Feb
YWG2:15 p.m.Winnipeg
16h 10m
2 stops
SJO6:25 a.m.San José Juan Santamaria Intl
11 Mar
SJO11:35 a.m.San José Juan Santamaria Intl
23h 04m
2 stops
YWG11:39 a.m.Winnipeg
C$ 694
Find similar
United Airlines
28 Feb
YWG2:15 p.m.Winnipeg
22h 41m
1 stop
SJO12:56 p.m.San José Juan Santamaria Intl
7 Mar
SJO2:20 p.m.San José Juan Santamaria Intl
20h 19m
2 stops
YWG10:39 a.m.Winnipeg
C$ 720
Find similar

Air Transat flights from Winnipeg to San José, San José Province

Our best Air Transat deals on Winnipeg to San José, San José Province flight tickets
Air Transat
24 Feb
YWG6:00 a.m.Winnipeg
17h 35m
1 stop
SJO11:35 p.m.San José Juan Santamaria Intl
12 Mar
SJO11:55 p.m.San José Juan Santamaria Intl
14h 35m
1 stop
YWG3:30 p.m.Winnipeg
C$ 831
Find similar
Air Transat
24 Feb
YWG6:00 a.m.Winnipeg
17h 35m
1 stop
SJO11:35 p.m.San José Juan Santamaria Intl
7 Mar
SJO11:55 p.m.San José Juan Santamaria Intl
14h 35m
1 stop
YWG2:30 p.m.Winnipeg
C$ 896
Find similar
Air Transat
28 Feb
YWG12:10 p.m.Winnipeg
11h 25m
1 stop
SJO11:35 p.m.San José Juan Santamaria Intl
7 Mar
SJO11:55 p.m.San José Juan Santamaria Intl
14h 35m
1 stop
YWG2:30 p.m.Winnipeg
C$ 1,053
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to San José, San José Province 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 1 September 2025.
Use the filters below to find and compare flights from Winnipeg to San José, San José Province that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 27/9

9:10 a.m.-10:27 a.m.

1 stop26h 17m

San José Juan Santamaria Intl

Sat 4/10

12:19 p.m.-9:41 a.m.

2 stops20h 22m

C$ 655

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 22/2

2:15 p.m.-12:56 p.m.

1 stop22h 41m

San José Juan Santamaria Intl

Wed 11/3

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

1 stop21h 34m

C$ 669

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 28/2

2:15 p.m.-6:25 a.m.

2 stops16h 10m

San José Juan Santamaria Intl

Wed 11/3

11:35 a.m.-11:39 a.m.

2 stops23h 04m

C$ 694

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 28/2

2:15 p.m.-12:56 p.m.

1 stop22h 41m

San José Juan Santamaria Intl

Sat 7/3

2:20 p.m.-10:39 a.m.

2 stops20h 19m

C$ 720

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 28/12

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

2 stops35h 59m

San José Juan Santamaria Intl

Wed 14/1

8:45 a.m.-11:57 a.m.

2 stops27h 12m

C$ 743

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 5/10

2:35 p.m.-10:41 a.m.

2 stops21h 06m

San José Juan Santamaria Intl

Sun 12/10

5:05 a.m.-9:41 a.m.

2 stops27h 36m

C$ 754

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 24/2

6:00 a.m.-11:35 p.m.

1 stop17h 35m

San José Juan Santamaria Intl

Thu 12/3

11:55 p.m.-3:30 p.m.

1 stop14h 35m

C$ 831

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 24/2

6:00 a.m.-11:35 p.m.

1 stop17h 35m

San José Juan Santamaria Intl

Sat 7/3

11:55 p.m.-2:30 p.m.

1 stop14h 35m

C$ 896

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 5/11

1:30 p.m.-10:55 p.m.

1 stop9h 25m

San José Juan Santamaria Intl

Wed 12/11

8:50 a.m.-8:28 p.m.

2 stops11h 38m

C$ 963

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 24/2

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

1 stop15h 00m

San José Juan Santamaria Intl

Wed 11/3

7:35 a.m.-7:24 p.m.

1 stop10h 49m

C$ 1,055

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Winnipeg to San José, San José Province

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, San José Province?

If you’re not able to fly to San José, San José Province in July, then September is your next best option. Flight prices from Winnipeg to San José, San José Province during September average around C$ 840.

What is the cheapest day to depart on your flight to San José, San José Province?

The cheapest day to depart from Winnipeg to San José, San José Province is on a Tuesday. Travellers who choose to depart for San José, San José Province on a Tuesday will often find tickets for as low as C$ 1,037. Flights from Winnipeg to San José, San José Province on a Thursday will generally be more expensive and average around C$ 1,345. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to San José, San José Province?

Our data shows that the cheapest Winnipeg to San José, San José Province flights are usually those with departure times at noon. Our users have found flights to San José, San José Province at noon for as low as C$ 775. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are C$ 1,350 on average. Flights to San José, San José Province from Winnipeg in the morning are generally more expensive because this time of day is more convenient for travellers’ schedules.

How far in advance should I book a flight to San José, San José Province?

You are more likely to see cheaper flights to San José, San José Province from Winnipeg when booking weeks ahead of your departure date. In general, you can expect to find flights to San José, San José Province for around C$ 1,158 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San José, San José Province from Winnipeg for as low as C$ 912 on momondo.

When to book flights from Winnipeg to San José, San José Province

Are you open to changing your travel dates? Check out the ideal times to fly from Winnipeg to San José, San José Province according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Winnipeg to San José, San José Province (YWG to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to San José, San José Province

Direct flights

None
There are no direct flights from Winnipeg to San José, San José Province. There are no popular flight routes from Winnipeg to San José, San José Province.
Search flight deals

  • 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. 9h 25m 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, San José Province?

Best airlines flying from Winnipeg to San José, San José Province

Compare and see reviews for airlines that fly from Winnipeg to San José, San José Province with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom C$ 663Free CancellationRating
7.4
8,936 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 1,000Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
AviancaPriceFrom C$ 1,225Free CancellationRating
6.7
2,423 reviews
Search Avianca 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
Heredia
Alajuela
Dominical
Santa Elena

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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