Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Winnipeg to San José from C$ 353

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. - 11:17 p.m.
SJO
-
YWG
15h 07m
1 stop
C$ 677Air Canada
Thu, 3 Sep - Fri, 25 Sep
Air Canada Logo
7:45 p.m. - 8:20 p.m.
YWG
-
SJO
25h 35m
2 stops
Air Canada Logo
7:10 a.m. - 8:00 p.m.
SJO
-
YWG
11h 50m
2 stops
C$ 689Air Canada
Thu, 3 Sep - Fri, 25 Sep
United Airlines Logo
7:00 a.m. - 12:21 p.m.
YWG
-
SJO
30h 21m
2 stops
United Airlines Logo
7:55 a.m. - 11:52 a.m.
SJO
-
YWG
26h 57m
2 stops
C$ 696United Airlines
Tue, 1 Sep - Fri, 11 Sep
United Airlines Logo
2:15 p.m. - 10:00 p.m.
YWG
-
SJO
55h 45m
2 stops
United Airlines Logo
8:45 a.m. - 8:48 p.m.
SJO
-
YWG
36h 03m
2 stops
C$ 717United Airlines
Wed, 25 Nov - Tue, 8 Dec
Air Canada Logo
8:05 a.m. - 11:50 p.m.
YWG
-
SJO
15h 45m
1 stop
Air Canada Logo
9:20 a.m. - 10:00 a.m.
SJO
-
YWG
24h 40m
1 stop
C$ 721Air Canada
Tue, 1 Dec - Wed, 2 Dec
Air Canada Logo
6:00 a.m. - 10:30 p.m.
YWG
-
SJO
16h 30m
2 stops
Air Canada Logo
9:20 a.m. - 10:00 a.m.
SJO
-
YWG
24h 40m
1 stop
C$ 726Air Canada
Tue, 1 Dec - Wed, 2 Dec
Air Canada Logo
6:55 p.m. - 10:30 p.m.
YWG
-
SJO
27h 35m
1 stop
Air Canada Logo
8:45 a.m. - 7:09 p.m.
SJO
-
YWG
10h 24m
1 stop
C$ 732Air Canada
Sun, 8 Nov - Tue, 17 Nov
United Airlines Logo
2:00 p.m. - 12:21 p.m.
YWG
-
SJO
23h 21m
2 stops
United Airlines Logo
7:55 a.m. - 10:33 p.m.
SJO
-
YWG
37h 38m
2 stops
C$ 736United Airlines
Tue, 1 Sep - Mon, 14 Sep
Air Canada Logo
6:00 a.m. - 10:30 p.m.
YWG
-
SJO
16h 30m
2 stops
Air Canada Logo
9:20 a.m. - 11:44 p.m.
SJO
-
YWG
14h 24m
2 stops
C$ 739Air Canada
Tue, 1 Dec - Wed, 2 Dec
United Airlines Logo
2:00 p.m. - 12:21 p.m.
YWG
-
SJO
23h 21m
2 stops
United Airlines Logo
1:25 p.m. - 11:52 a.m.
SJO
-
YWG
21h 27m
2 stops
C$ 746United Airlines
Sat, 29 Aug - Tue, 15 Sep

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

Air Canada flights from Winnipeg to San José

Our best Air Canada deals on Winnipeg to San José flight tickets
Air Canada
3 Sep
YWG4:10 p.m.Winnipeg
29h 10m
1 stop
SJO8:20 p.m.San José Juan Santamaria Intl
25 Sep
SJO7:10 a.m.San José Juan Santamaria Intl
15h 07m
1 stop
YWG11:17 p.m.Winnipeg
C$ 677
Air Canada
3 Sep
YWG7:45 p.m.Winnipeg
25h 35m
2 stops
SJO8:20 p.m.San José Juan Santamaria Intl
25 Sep
SJO7:10 a.m.San José Juan Santamaria Intl
11h 50m
2 stops
YWG8:00 p.m.Winnipeg
C$ 689
Air Canada
1 Dec
YWG8:05 a.m.Winnipeg
15h 45m
1 stop
SJO11:50 p.m.San José Juan Santamaria Intl
2 Dec
SJO9:20 a.m.San José Juan Santamaria Intl
24h 40m
1 stop
YWG10:00 a.m.Winnipeg
C$ 721

Avianca flights from Winnipeg to San José

Our best Avianca deals on Winnipeg to San José flight tickets
Avianca
28 Nov
YWG7:15 a.m.Winnipeg
16h 25m
2 stops
SJO11:40 p.m.San José Juan Santamaria Intl
18 Dec
SJO3:05 p.m.San José Juan Santamaria Intl
19h 04m
2 stops
YWG10:09 a.m.Winnipeg
C$ 931
Avianca
8 Nov
YWG7:15 a.m.Winnipeg
28h 30m
3 stops
SJO11:45 a.m.San José Juan Santamaria Intl
17 Nov
SJO5:00 a.m.San José Juan Santamaria Intl
16h 14m
2 stops
YWG9:14 p.m.Winnipeg
C$ 935
Avianca
8 Nov
YWG7:15 a.m.Winnipeg
28h 30m
3 stops
SJO11:45 a.m.San José Juan Santamaria Intl
17 Nov
SJO5:00 a.m.San José Juan Santamaria Intl
16h 14m
2 stops
YWG9:14 p.m.Winnipeg
C$ 940

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 18 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

Thu 3/9

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

1 stop29h 10m

San José Juan Santamaria Intl

Fri 25/9

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

1 stop15h 07m

C$ 677

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 3/9

7:45 p.m.-8:20 p.m.

2 stops25h 35m

San José Juan Santamaria Intl

Fri 25/9

7:10 a.m.-8:00 p.m.

2 stops11h 50m

C$ 689

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 1/9

7:00 a.m.-12:21 p.m.

2 stops30h 21m

San José Juan Santamaria Intl

Fri 11/9

7:55 a.m.-11:52 a.m.

2 stops26h 57m

C$ 696

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 25/11

2:15 p.m.-10:00 p.m.

2 stops55h 45m

San José Juan Santamaria Intl

Tue 8/12

8:45 a.m.-8:48 p.m.

2 stops36h 03m

C$ 717

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 1/12

8:05 a.m.-11:50 p.m.

1 stop15h 45m

San José Juan Santamaria Intl

Wed 2/12

9:20 a.m.-10:00 a.m.

1 stop24h 40m

C$ 721

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 1/12

6:00 a.m.-10:30 p.m.

2 stops16h 30m

San José Juan Santamaria Intl

Wed 2/12

9:20 a.m.-10:00 a.m.

1 stop24h 40m

C$ 726

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.-7:09 p.m.

1 stop10h 24m

C$ 732

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 1/9

2:00 p.m.-12:21 p.m.

2 stops23h 21m

San José Juan Santamaria Intl

Mon 14/9

7:55 a.m.-10:33 p.m.

2 stops37h 38m

C$ 736
Quickest round-trip

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 1/12

6:00 a.m.-10:30 p.m.

2 stops16h 30m

San José Juan Santamaria Intl

Wed 2/12

9:20 a.m.-11:44 p.m.

2 stops14h 24m

C$ 739

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 29/8

2:00 p.m.-12:21 p.m.

2 stops23h 21m

San José Juan Santamaria Intl

Tue 15/9

1:25 p.m.-11:52 a.m.

2 stops21h 27m

C$ 746

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$ 687.

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$ 682Free CancellationRating
7.4
10,006 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 832Free CancellationRating
7.1
11,352 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
Mon 17/8
Mon 24/8
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