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Cheap flights from Winnipeg to San José from C$ 276

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

Multiple Airlines Logo
5:00 a.m. - 11:35 p.m.YWG-SJO
19h 35m1 stop
Multiple Airlines Logo
1:19 p.m. - 3:07 p.m.SJO-YWG
25h 48m2 stops
C$ 662Multiple Airlines
Find Deal
Sat, 1 Nov - Sat, 15 Nov
United Airlines Logo
2:20 p.m. - 6:16 p.m.YWG-SJO
27h 56m2 stops
United Airlines Logo
1:20 p.m. - 11:39 a.m.SJO-YWG
21h 19m2 stops
C$ 666United Airlines
Find Deal
Tue, 3 Mar - Tue, 10 Mar
United Airlines Logo
2:20 p.m. - 1:15 p.m.YWG-SJO
22h 55m2 stops
United Airlines Logo
5:30 a.m. - 11:39 a.m.SJO-YWG
29h 09m2 stops
C$ 667United Airlines
Find Deal
Tue, 3 Mar - Tue, 10 Mar
United Airlines Logo
2:20 p.m. - 1:15 p.m.YWG-SJO
22h 55m2 stops
United Airlines Logo
11:35 a.m. - 11:39 a.m.SJO-YWG
23h 04m2 stops
C$ 670United Airlines
Find Deal
Tue, 3 Mar - Tue, 10 Mar
Multiple Airlines Logo
8:00 a.m. - 11:40 p.m.YWG-SJO
16h 40m2 stops
Multiple Airlines Logo
1:19 p.m. - 3:07 p.m.SJO-YWG
25h 48m2 stops
C$ 758Multiple Airlines
Find Deal
Sat, 1 Nov - Sat, 15 Nov
Air Transat Logo
12:10 p.m. - 11:35 p.m.YWG-SJO
11h 25m1 stop
Air Transat Logo
11:55 p.m. - 11:35 p.m.SJO-YWG
22h 40m1 stop
C$ 860Air Transat
Find Deal
Tue, 3 Mar - Tue, 10 Mar
Air Transat Logo
12:10 p.m. - 11:35 p.m.YWG-SJO
11h 25m1 stop
Air Transat Logo
11:55 p.m. - 11:35 p.m.SJO-YWG
22h 40m1 stop
C$ 863Air Transat
Find Deal
Tue, 3 Mar - Tue, 10 Mar
Delta Logo
5:38 p.m. - 12:55 p.m.YWG-SJO
19h 17m2 stops
Delta Logo
1:20 p.m. - 11:43 a.m.SJO-YWG
21h 23m2 stops
C$ 1,110Delta
Find Deal
Fri, 6 Mar - Fri, 20 Mar
Air Canada Logo
11:05 a.m. - 12:05 a.m.YWG-SJO
13h 00m1 stop
Air Canada Logo
7:35 a.m. - 9:49 a.m.SJO-YWG
25h 14m1 stop
C$ 1,151Air Canada
Find Deal
Fri, 6 Mar - Fri, 20 Mar
Air Canada Logo
7:15 a.m. - 12:05 a.m.YWG-SJO
16h 50m1 stop
Air Canada Logo
7:35 a.m. - 9:49 a.m.SJO-YWG
25h 14m1 stop
C$ 1,156Air Canada
Find Deal
Fri, 6 Mar - Fri, 20 Mar

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

Our best Air Canada deals on Winnipeg to San José, San José Province flight tickets
Air Canada
6 Mar
YWG11:05 a.m.Winnipeg
13h 00m
1 stop
SJO12:05 a.m.San José Juan Santamaria Intl
20 Mar
SJO7:35 a.m.San José Juan Santamaria Intl
25h 14m
1 stop
YWG9:49 a.m.Winnipeg
C$ 1,151
Find similar
Air Canada
6 Mar
YWG7:15 a.m.Winnipeg
16h 50m
1 stop
SJO12:05 a.m.San José Juan Santamaria Intl
20 Mar
SJO7:35 a.m.San José Juan Santamaria Intl
25h 14m
1 stop
YWG9:49 a.m.Winnipeg
C$ 1,156
Find similar
Air Canada
6 Mar
YWG7:15 a.m.Winnipeg
16h 00m
2 stops
SJO11:15 p.m.San José Juan Santamaria Intl
20 Mar
SJO7:35 a.m.San José Juan Santamaria Intl
25h 41m
2 stops
YWG10:16 a.m.Winnipeg
C$ 1,235
Find similar

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
3 Mar
YWG2:20 p.m.Winnipeg
27h 56m
2 stops
SJO6:16 p.m.San José Juan Santamaria Intl
10 Mar
SJO1:20 p.m.San José Juan Santamaria Intl
21h 19m
2 stops
YWG11:39 a.m.Winnipeg
C$ 666
Find similar
United Airlines
3 Mar
YWG2:20 p.m.Winnipeg
22h 55m
2 stops
SJO1:15 p.m.San José Juan Santamaria Intl
10 Mar
SJO5:30 a.m.San José Juan Santamaria Intl
29h 09m
2 stops
YWG11:39 a.m.Winnipeg
C$ 667
Find similar
United Airlines
3 Mar
YWG2:20 p.m.Winnipeg
22h 55m
2 stops
SJO1:15 p.m.San José Juan Santamaria Intl
10 Mar
SJO11:35 a.m.San José Juan Santamaria Intl
23h 04m
2 stops
YWG11:39 a.m.Winnipeg
C$ 670
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 17 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 1/11

5:00 a.m.-11:35 p.m.

1 stop19h 35m

San José Juan Santamaria Intl

Sat 15/11

1:19 p.m.-3:07 p.m.

2 stops25h 48m

C$ 662

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 3/3

2:20 p.m.-6:16 p.m.

2 stops27h 56m

San José Juan Santamaria Intl

Tue 10/3

1:20 p.m.-11:39 a.m.

2 stops21h 19m

C$ 666

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 3/3

2:20 p.m.-1:15 p.m.

2 stops22h 55m

San José Juan Santamaria Intl

Tue 10/3

5:30 a.m.-11:39 a.m.

2 stops29h 09m

C$ 667

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 3/3

2:20 p.m.-1:15 p.m.

2 stops22h 55m

San José Juan Santamaria Intl

Tue 10/3

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

2 stops23h 04m

C$ 670

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 1/11

8:00 a.m.-11:40 p.m.

2 stops16h 40m

San José Juan Santamaria Intl

Sat 15/11

1:19 p.m.-3:07 p.m.

2 stops25h 48m

C$ 758

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 3/3

12:10 p.m.-11:35 p.m.

1 stop11h 25m

San José Juan Santamaria Intl

Tue 10/3

11:55 p.m.-11:35 p.m.

1 stop22h 40m

C$ 860

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 3/3

12:10 p.m.-11:35 p.m.

1 stop11h 25m

San José Juan Santamaria Intl

Tue 10/3

11:55 p.m.-11:35 p.m.

1 stop22h 40m

C$ 863

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 6/3

5:38 p.m.-12:55 p.m.

2 stops19h 17m

San José Juan Santamaria Intl

Fri 20/3

1:20 p.m.-11:43 a.m.

2 stops21h 23m

C$ 1,110

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 6/3

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

1 stop13h 00m

San José Juan Santamaria Intl

Fri 20/3

7:35 a.m.-9:49 a.m.

1 stop25h 14m

C$ 1,151

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 6/3

7:15 a.m.-12:05 a.m.

1 stop16h 50m

San José Juan Santamaria Intl

Fri 20/3

7:35 a.m.-9:49 a.m.

1 stop25h 14m

C$ 1,156

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$ 841.

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$ 1,038. Flights from Winnipeg to San José, San José Province on a Thursday will generally be more expensive and average around C$ 1,346. 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$ 776. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are C$ 1,352 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$ 1,155 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$ 876 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. 11h 15m 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
8,926 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 1,002Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
AviancaPriceFrom C$ 1,226Free CancellationRating
6.7
2,436 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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