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Cheap flights from Winnipeg to San José from C$ 297

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 17/2. 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.
Multiple Airlines Logo
12:20 p.m. - 11:37 a.m.
YWG
-
SJO
23h 17m2 stops
Multiple Airlines Logo
12:33 p.m. - 5:26 p.m.
SJO
-
YWG
28h 53m1 stop
C$ 611Multiple Airlines
Mon, 2 Feb - Mon, 9 Feb
Multiple Airlines Logo
12:20 p.m. - 11:37 a.m.
YWG
-
SJO
23h 17m2 stops
Multiple Airlines Logo
12:33 p.m. - 7:09 p.m.
SJO
-
YWG
30h 36m2 stops
C$ 625Multiple Airlines
Mon, 2 Feb - Mon, 9 Feb
Multiple Airlines Logo
8:00 a.m. - 11:19 a.m.
YWG
-
SJO
28h 19m1 stop
Multiple Airlines Logo
12:31 p.m. - 7:09 p.m.
SJO
-
YWG
29h 38m2 stops
C$ 650Multiple Airlines
Mon, 23 Mar - Thu, 9 Apr
Multiple Airlines Logo
8:00 a.m. - 11:19 a.m.
YWG
-
SJO
28h 19m1 stop
Multiple Airlines Logo
12:31 p.m. - 3:09 p.m.
SJO
-
YWG
25h 38m2 stops
C$ 657Multiple Airlines
Mon, 23 Mar - Tue, 7 Apr
Multiple Airlines Logo
9:25 a.m. - 10:35 p.m.
YWG
-
SJO
14h 10m1 stop
Multiple Airlines Logo
12:31 p.m. - 12:02 a.m.
SJO
-
YWG
34h 31m2 stops
C$ 663Multiple Airlines
Thu, 30 Apr - Wed, 13 May
Multiple Airlines Logo
8:00 a.m. - 11:37 a.m.
YWG
-
SJO
27h 37m2 stops
Multiple Airlines Logo
12:55 a.m. - 7:35 p.m.
SJO
-
YWG
18h 40m1 stop
C$ 665Multiple Airlines
Mon, 2 Feb - Thu, 5 Feb
Multiple Airlines Logo
8:00 a.m. - 10:42 a.m.
YWG
-
SJO
27h 42m1 stop
Multiple Airlines Logo
12:31 p.m. - 7:09 p.m.
SJO
-
YWG
29h 38m2 stops
C$ 670Multiple Airlines
Tue, 31 Mar - Wed, 8 Apr
United Airlines Logo
2:20 p.m. - 6:16 p.m.
YWG
-
SJO
27h 56m2 stops
United Airlines Logo
1:05 p.m. - 11:57 a.m.
SJO
-
YWG
21h 52m1 stop
C$ 672United Airlines
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. - 11:57 a.m.
SJO
-
YWG
23h 22m2 stops
C$ 673United Airlines
Tue, 3 Mar - Tue, 10 Mar
Multiple Airlines Logo
12:20 p.m. - 11:35 p.m.
YWG
-
SJO
11h 15m1 stop
Multiple Airlines Logo
12:35 p.m. - 3:09 p.m.
SJO
-
YWG
26h 34m2 stops
C$ 681Multiple Airlines
Tue, 24 Feb - Thu, 5 Mar

United Airlines flights from Winnipeg to San José

Our best United Airlines deals on Winnipeg to San José flight tickets
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 22m
2 stops
YWG11:57 a.m.Winnipeg
C$ 672
United Airlines
3 Mar
YWG2:20 p.m.Winnipeg
27h 56m
2 stops
SJO6:16 p.m.San José Juan Santamaria Intl
10 Mar
SJO1:05 p.m.San José Juan Santamaria Intl
21h 52m
1 stop
YWG11:57 a.m.Winnipeg
C$ 673
United Airlines
24 Mar
YWG2:20 p.m.Winnipeg
22h 36m
1 stop
SJO11:56 a.m.San José Juan Santamaria Intl
8 Apr
SJO7:55 a.m.San José Juan Santamaria Intl
26h 57m
2 stops
YWG11:52 a.m.Winnipeg
C$ 688

Avianca flights from Winnipeg to San José

Our best Avianca deals on Winnipeg to San José flight tickets
Avianca
18 Jan
YWG7:05 p.m.Winnipeg
23h 50m
2 stops
SJO6:55 p.m.San José Juan Santamaria Intl
26 Jan
SJO4:30 p.m.San José Juan Santamaria Intl
17h 19m
2 stops
YWG9:49 a.m.Winnipeg
C$ 856
Avianca
18 Jan
YWG7:05 p.m.Winnipeg
23h 50m
2 stops
SJO6:55 p.m.San José Juan Santamaria Intl
28 Jan
SJO4:30 p.m.San José Juan Santamaria Intl
17h 19m
2 stops
YWG9:49 a.m.Winnipeg
C$ 882
Avianca
18 Jan
YWG7:05 p.m.Winnipeg
23h 50m
2 stops
SJO6:55 p.m.San José Juan Santamaria Intl
23 Jan
SJO12:40 p.m.San José Juan Santamaria Intl
24h 04m
3 stops
YWG12:44 p.m.Winnipeg
C$ 883

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 8 January 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

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 2/2

12:20 p.m.-11:37 a.m.

2 stops23h 17m

San José Juan Santamaria Intl

Mon 9/2

12:33 p.m.-5:26 p.m.

1 stop28h 53m

C$ 611

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 2/2

12:20 p.m.-11:37 a.m.

2 stops23h 17m

San José Juan Santamaria Intl

Mon 9/2

12:33 p.m.-7:09 p.m.

2 stops30h 36m

C$ 625

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 23/3

8:00 a.m.-11:19 a.m.

1 stop28h 19m

San José Juan Santamaria Intl

Thu 9/4

12:31 p.m.-7:09 p.m.

2 stops29h 38m

C$ 650

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 23/3

8:00 a.m.-11:19 a.m.

1 stop28h 19m

San José Juan Santamaria Intl

Tue 7/4

12:31 p.m.-3:09 p.m.

2 stops25h 38m

C$ 657

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 30/4

9:25 a.m.-10:35 p.m.

1 stop14h 10m

San José Juan Santamaria Intl

Wed 13/5

12:31 p.m.-12:02 a.m.

2 stops34h 31m

C$ 663

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 2/2

8:00 a.m.-11:37 a.m.

2 stops27h 37m

San José Juan Santamaria Intl

Thu 5/2

12:55 a.m.-7:35 p.m.

1 stop18h 40m

C$ 665

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 31/3

8:00 a.m.-10:42 a.m.

1 stop27h 42m

San José Juan Santamaria Intl

Wed 8/4

12:31 p.m.-7:09 p.m.

2 stops29h 38m

C$ 670

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

1:05 p.m.-11:57 a.m.

1 stop21h 52m

C$ 672

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.-11:57 a.m.

2 stops23h 22m

C$ 673

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 24/2

12:20 p.m.-11:35 p.m.

1 stop11h 15m

San José Juan Santamaria Intl

Thu 5/3

12:35 p.m.-3:09 p.m.

2 stops26h 34m

C$ 681

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, 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$ 818. If you aren’t able to travel during the month of July, then book flights to San José from Winnipeg during September instead. Flights to San José in September, while not as cheap as those in July, still average around C$ 845.

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

You are more likely to see cheaper flights to San José from Winnipeg when booking weeks ahead of your departure date. In general, you can expect to find flights to San José for around C$ 1,147 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San José from Winnipeg for as low as C$ 806 on momondo.

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

15h 09m

Direct flights

None
The fastest flight from Winnipeg to San José takes 15h 09m
There are no direct flights from Winnipeg to San José. There are no popular flight routes from Winnipeg to San José.
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. 15h 09m 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$ 668Free CancellationRating
7.4
9,142 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 1,008Free CancellationRating
7.1
10,603 reviews
Search Air Canada flights
AviancaPriceFrom C$ 1,232Free CancellationRating
6.6
2,491 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
Dominical
Monteverde
Heredia
Alajuela
San Gerardo de Dota
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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