Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Winnipeg to San José from C$ 376

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 25/8. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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
4:10 p.m. - 8:20 p.m.
YWG
-
SJO
29h 10m
1 stop
Air Canada Logo
7:10 a.m. - 9:27 p.m.
SJO
-
YWG
13h 17m
1 stop
C$ 729Air Canada
Tue, 1 Sep - Wed, 30 Sep
Air Canada Logo
4:05 p.m. - 8:20 p.m.
YWG
-
SJO
29h 15m
1 stop
Air Canada Logo
7:10 a.m. - 11:17 p.m.
SJO
-
YWG
15h 07m
1 stop
C$ 732Air Canada
Tue, 1 Sep - Wed, 16 Sep
Air Canada Logo
1:30 p.m. - 8:20 p.m.
YWG
-
SJO
31h 50m
2 stops
Air Canada Logo
7:10 a.m. - 9:14 p.m.
SJO
-
YWG
13h 04m
2 stops
C$ 736Air Canada
Tue, 1 Sep - Wed, 16 Sep
Air Canada Logo
5:25 p.m. - 10:00 p.m.
YWG
-
SJO
29h 35m
1 stop
Air Canada Logo
7:10 a.m. - 6:12 p.m.
SJO
-
YWG
10h 02m
1 stop
C$ 739Air Canada
Mon, 31 Aug - Wed, 16 Sep
Air Canada Logo
6:55 p.m. - 10:30 p.m.
YWG
-
SJO
27h 35m
1 stop
Air Canada Logo
8:45 a.m. - 9:14 p.m.
SJO
-
YWG
12h 29m
1 stop
C$ 740Air Canada
Sun, 8 Nov - Tue, 17 Nov
Air Canada Logo
6:55 p.m. - 10:30 p.m.
YWG
-
SJO
27h 35m
1 stop
Air Canada Logo
8:45 a.m. - 9:14 p.m.
SJO
-
YWG
12h 29m
1 stop
C$ 742Air Canada
Sun, 8 Nov - Tue, 17 Nov
Air Canada Logo
6:55 p.m. - 10:30 p.m.
YWG
-
SJO
27h 35m
1 stop
Air Canada Logo
8:45 a.m. - 10:00 a.m.
SJO
-
YWG
25h 15m
2 stops
C$ 744Air Canada
Sun, 8 Nov - Tue, 17 Nov
Air Canada Logo
6:55 p.m. - 10:30 p.m.
YWG
-
SJO
27h 35m
1 stop
Air Canada Logo
8:45 a.m. - 10:00 a.m.
SJO
-
YWG
25h 15m
2 stops
C$ 746Air Canada
Sun, 8 Nov - Tue, 17 Nov
Air Canada Logo
7:55 a.m. - 10:00 p.m.
YWG
-
SJO
15h 05m
2 stops
Air Canada Logo
7:10 a.m. - 9:59 a.m.
SJO
-
YWG
25h 49m
2 stops
C$ 747Air Canada
Mon, 31 Aug - Wed, 16 Sep
Air Canada Logo
6:00 a.m. - 10:50 p.m.
YWG
-
SJO
41h 50m
2 stops
Air Canada Logo
8:20 a.m. - 7:25 p.m.
SJO
-
YWG
34h 05m
2 stops
C$ 750Air Canada
Thu, 29 Oct - Sat, 31 Oct

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

United Airlines flights from Winnipeg to San José

Our best United Airlines deals on Winnipeg to San José flight tickets
United Airlines
14 Oct
YWG7:00 a.m.Winnipeg
30h 21m
2 stops
SJO12:21 p.m.San José Juan Santamaria Intl
21 Oct
SJO7:55 a.m.San José Juan Santamaria Intl
13h 38m
2 stops
YWG10:33 p.m.Winnipeg
C$ 800
United Airlines
31 Aug
YWG8:45 a.m.Winnipeg
28h 36m
2 stops
SJO12:21 p.m.San José Juan Santamaria Intl
15 Sep
SJO1:25 p.m.San José Juan Santamaria Intl
21h 27m
2 stops
YWG11:52 a.m.Winnipeg
C$ 803
United Airlines
29 Aug
YWG2:00 p.m.Winnipeg
23h 21m
2 stops
SJO12:21 p.m.San José Juan Santamaria Intl
9 Sep
SJO1:25 p.m.San José Juan Santamaria Intl
21h 27m
2 stops
YWG11:52 a.m.Winnipeg
C$ 828

Air Canada flights from Winnipeg to San José

Our best Air Canada deals on Winnipeg to San José flight tickets
Air Canada
1 Sep
YWG4:10 p.m.Winnipeg
29h 10m
1 stop
SJO8:20 p.m.San José Juan Santamaria Intl
30 Sep
SJO7:10 a.m.San José Juan Santamaria Intl
13h 17m
1 stop
YWG9:27 p.m.Winnipeg
C$ 729
Air Canada
1 Sep
YWG4:05 p.m.Winnipeg
29h 15m
1 stop
SJO8:20 p.m.San José Juan Santamaria Intl
16 Sep
SJO7:10 a.m.San José Juan Santamaria Intl
15h 07m
1 stop
YWG11:17 p.m.Winnipeg
C$ 732
Air Canada
1 Sep
YWG1:30 p.m.Winnipeg
31h 50m
2 stops
SJO8:20 p.m.San José Juan Santamaria Intl
16 Sep
SJO7:10 a.m.San José Juan Santamaria Intl
13h 04m
2 stops
YWG9:14 p.m.Winnipeg
C$ 736

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 12 July 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

Tue 1/9

4:10 p.m.-8:20 p.m.

1 stop29h 10m

San José Juan Santamaria Intl

Wed 30/9

7:10 a.m.-9:27 p.m.

1 stop13h 17m

C$ 729

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 1/9

4:05 p.m.-8:20 p.m.

1 stop29h 15m

San José Juan Santamaria Intl

Wed 16/9

7:10 a.m.-11:17 p.m.

1 stop15h 07m

C$ 732

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 1/9

1:30 p.m.-8:20 p.m.

2 stops31h 50m

San José Juan Santamaria Intl

Wed 16/9

7:10 a.m.-9:14 p.m.

2 stops13h 04m

C$ 736
Quickest round-trip

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 31/8

5:25 p.m.-10:00 p.m.

1 stop29h 35m

San José Juan Santamaria Intl

Wed 16/9

7:10 a.m.-6:12 p.m.

1 stop10h 02m

C$ 739

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 8/11

6:55 p.m.-10:30 p.m.

1 stop27h 35m

San José Juan Santamaria Intl

Tue 17/11

8:45 a.m.-9:14 p.m.

1 stop12h 29m

C$ 740

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 8/11

6:55 p.m.-10:30 p.m.

1 stop27h 35m

San José Juan Santamaria Intl

Tue 17/11

8:45 a.m.-9:14 p.m.

1 stop12h 29m

C$ 742

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 8/11

6:55 p.m.-10:30 p.m.

1 stop27h 35m

San José Juan Santamaria Intl

Tue 17/11

8:45 a.m.-10:00 a.m.

2 stops25h 15m

C$ 744

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 8/11

6:55 p.m.-10:30 p.m.

1 stop27h 35m

San José Juan Santamaria Intl

Tue 17/11

8:45 a.m.-10:00 a.m.

2 stops25h 15m

C$ 746

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 31/8

7:55 a.m.-10:00 p.m.

2 stops15h 05m

San José Juan Santamaria Intl

Wed 16/9

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

2 stops25h 49m

C$ 747

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 29/10

6:00 a.m.-10:50 p.m.

2 stops41h 50m

San José Juan Santamaria Intl

Sat 31/10

8:20 a.m.-7:25 p.m.

2 stops34h 05m

C$ 750

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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, 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 May instead. Flights to San José in May, while not as cheap as those in October, still average around C$ 694.

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

13h 37m

Direct flights

None
The fastest flight from Winnipeg to San José takes 13h 37m
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. 13h 37m 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$ 688Free CancellationRating
7.4
9,979 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 840Free CancellationRating
7.1
11,331 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
Manuel Antonio
Jacó
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.

An easier way to manage your San José trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 11/8
Tue 18/8
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Costa Rica

Airports servicing Costa Rica

Liberia Airport