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Cheap flights from Winnipeg to San José from C$ 390

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 15/9. 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
7:10 p.m. - 10:00 p.m.
YWG
-
SJO
27h 50m
1 stop
Air Canada Logo
7:10 a.m. - 11:12 a.m.
SJO
-
YWG
27h 02m
1 stop
C$ 747Air Canada
Wed, 23 Sep - Sun, 27 Sep
Air Canada Logo
1:25 p.m. - 10:00 p.m.
YWG
-
SJO
33h 35m
2 stops
Air Canada Logo
7:10 a.m. - 9:59 a.m.
SJO
-
YWG
25h 49m
2 stops
C$ 752Air Canada
Wed, 23 Sep - Sun, 27 Sep
United Airlines Logo
7:00 a.m. - 7:37 p.m.
YWG
-
SJO
13h 37m
2 stops
United Airlines Logo
1:25 p.m. - 10:24 p.m.
SJO
-
YWG
31h 59m
2 stops
C$ 755United Airlines
Wed, 23 Sep - Sun, 27 Sep
Air Canada Logo
5:15 a.m. - 10:05 p.m.
YWG
-
SJO
16h 50m
1 stop
Air Canada Logo
8:35 a.m. - 10:39 p.m.
SJO
-
YWG
14h 04m
1 stop
C$ 770Air Canada
Sun, 8 Nov - Tue, 17 Nov
Air Canada Logo
6:00 a.m. - 10:15 p.m.
YWG
-
SJO
17h 15m
2 stops
Air Canada Logo
9:50 a.m. - 10:16 a.m.
SJO
-
YWG
24h 26m
1 stop
C$ 773Air Canada
Fri, 30 Oct - Sat, 7 Nov
Air Canada Logo
8:15 a.m. - 10:15 p.m.
YWG
-
SJO
15h 00m
1 stop
Air Canada Logo
9:50 a.m. - 10:16 a.m.
SJO
-
YWG
24h 26m
1 stop
C$ 778Air Canada
Fri, 30 Oct - Sat, 7 Nov
Air Canada Logo
4:05 p.m. - 10:15 p.m.
YWG
-
SJO
31h 10m
1 stop
Air Canada Logo
9:50 a.m. - 11:16 a.m.
SJO
-
YWG
24h 26m
1 stop
C$ 780Air Canada
Sat, 24 Oct - Sat, 31 Oct
Air Canada Logo
4:05 p.m. - 10:15 p.m.
YWG
-
SJO
31h 10m
1 stop
Air Canada Logo
9:50 a.m. - 10:16 a.m.
SJO
-
YWG
24h 26m
1 stop
C$ 784Air Canada
Sat, 24 Oct - Mon, 9 Nov
Air Canada Logo
6:00 a.m. - 10:15 p.m.
YWG
-
SJO
17h 15m
2 stops
Air Canada Logo
9:50 a.m. - 9:44 a.m.
SJO
-
YWG
23h 54m
2 stops
C$ 788Air Canada
Fri, 30 Oct - Sat, 7 Nov
Air Canada Logo
7:10 p.m. - 10:15 p.m.
YWG
-
SJO
28h 05m
2 stops
Air Canada Logo
9:50 a.m. - 11:16 a.m.
SJO
-
YWG
24h 26m
1 stop
C$ 790Air Canada
Sat, 24 Oct - Sat, 31 Oct

Air Canada flights from Winnipeg to San José

Our best Air Canada deals on Winnipeg to San José flight tickets
Air Canada
23 Sep
YWG7:10 p.m.Winnipeg
27h 50m
1 stop
SJO10:00 p.m.San José Juan Santamaria Intl
27 Sep
SJO7:10 a.m.San José Juan Santamaria Intl
27h 02m
1 stop
YWG11:12 a.m.Winnipeg
C$ 747
Air Canada
23 Sep
YWG1:25 p.m.Winnipeg
33h 35m
2 stops
SJO10:00 p.m.San José Juan Santamaria Intl
27 Sep
SJO7:10 a.m.San José Juan Santamaria Intl
25h 49m
2 stops
YWG9:59 a.m.Winnipeg
C$ 752
Air Canada
8 Nov
YWG5:15 a.m.Winnipeg
16h 50m
1 stop
SJO10:05 p.m.San José Juan Santamaria Intl
17 Nov
SJO8:35 a.m.San José Juan Santamaria Intl
14h 04m
1 stop
YWG10:39 p.m.Winnipeg
C$ 770

United Airlines flights from Winnipeg to San José

Our best United Airlines deals on Winnipeg to San José flight tickets
United Airlines
23 Sep
YWG7:00 a.m.Winnipeg
13h 37m
2 stops
SJO7:37 p.m.San José Juan Santamaria Intl
27 Sep
SJO1:25 p.m.San José Juan Santamaria Intl
31h 59m
2 stops
YWG10:24 p.m.Winnipeg
C$ 755
United Airlines
26 Oct
YWG8:30 a.m.Winnipeg
28h 45m
2 stops
SJO12:15 p.m.San José Juan Santamaria Intl
11 Nov
SJO12:35 p.m.San José Juan Santamaria Intl
23h 04m
2 stops
YWG11:39 a.m.Winnipeg
C$ 858
United Airlines
6 Jun
YWG8:45 a.m.Winnipeg
35h 52m
2 stops
SJO7:37 p.m.San José Juan Santamaria Intl
15 Jun
SJO12:30 a.m.San José Juan Santamaria Intl
21h 08m
2 stops
YWG10:38 p.m.Winnipeg
C$ 859

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 13 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

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 23/9

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

1 stop27h 50m

San José Juan Santamaria Intl

Sun 27/9

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

1 stop27h 02m

C$ 747

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 23/9

1:25 p.m.-10:00 p.m.

2 stops33h 35m

San José Juan Santamaria Intl

Sun 27/9

7:10 a.m.-9:59 a.m.

2 stops25h 49m

C$ 752

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 23/9

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

2 stops13h 37m

San José Juan Santamaria Intl

Sun 27/9

1:25 p.m.-10:24 p.m.

2 stops31h 59m

C$ 755
Quickest round-trip

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 8/11

5:15 a.m.-10:05 p.m.

1 stop16h 50m

San José Juan Santamaria Intl

Tue 17/11

8:35 a.m.-10:39 p.m.

1 stop14h 04m

C$ 770

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 30/10

6:00 a.m.-10:15 p.m.

2 stops17h 15m

San José Juan Santamaria Intl

Sat 7/11

9:50 a.m.-10:16 a.m.

1 stop24h 26m

C$ 773

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 30/10

8:15 a.m.-10:15 p.m.

1 stop15h 00m

San José Juan Santamaria Intl

Sat 7/11

9:50 a.m.-10:16 a.m.

1 stop24h 26m

C$ 778

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 24/10

4:05 p.m.-10:15 p.m.

1 stop31h 10m

San José Juan Santamaria Intl

Sat 31/10

9:50 a.m.-11:16 a.m.

1 stop24h 26m

C$ 780

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 24/10

4:05 p.m.-10:15 p.m.

1 stop31h 10m

San José Juan Santamaria Intl

Mon 9/11

9:50 a.m.-10:16 a.m.

1 stop24h 26m

C$ 784

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 30/10

6:00 a.m.-10:15 p.m.

2 stops17h 15m

San José Juan Santamaria Intl

Sat 7/11

9:50 a.m.-9:44 a.m.

2 stops23h 54m

C$ 788

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 24/10

7:10 p.m.-10:15 p.m.

2 stops28h 05m

San José Juan Santamaria Intl

Sat 31/10

9:50 a.m.-11:16 a.m.

1 stop24h 26m

C$ 790

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, October 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$ 0. If you aren’t able to travel during the month of October, then book flights to San José from Winnipeg during April instead. Flights to San José in April, while not as cheap as those in October, still average around C$ 773.

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

22h 15m

Direct flights

None
The fastest flight from Winnipeg to San José takes 22h 15m
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. 22h 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?

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$ 666Free CancellationRating
7.4
9,706 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 970Free CancellationRating
7.1
11,026 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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