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Cheap flights from Winnipeg to San José from C$ 428

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 25/4. 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
7:20 p.m. - 10:00 p.m.
YWG
-
SJO
27h 40m
1 stop
Air Canada Logo
7:40 a.m. - 10:09 a.m.
SJO
-
YWG
25h 29m
1 stop
C$ 752Air Canada
Fri, 15 May - Mon, 1 Jun
Air Canada Logo
5:10 a.m. - 8:35 p.m.
YWG
-
SJO
16h 25m
2 stops
Air Canada Logo
7:40 a.m. - 10:09 a.m.
SJO
-
YWG
25h 29m
1 stop
C$ 756Air Canada
Fri, 15 May - Mon, 1 Jun
United Airlines Logo
7:00 a.m. - 10:11 a.m.
YWG
-
SJO
28h 11m
2 stops
United Airlines Logo
12:30 a.m. - 10:33 p.m.
SJO
-
YWG
21h 03m
2 stops
C$ 761United Airlines
Tue, 30 Jun - Mon, 6 Jul
United Airlines Logo
7:00 a.m. - 10:39 p.m.
YWG
-
SJO
16h 39m
2 stops
United Airlines Logo
1:25 p.m. - 10:33 p.m.
SJO
-
YWG
32h 08m
2 stops
C$ 786United Airlines
Thu, 25 Jun - Fri, 10 Jul
United Airlines Logo
7:00 a.m. - 10:39 p.m.
YWG
-
SJO
16h 39m
2 stops
United Airlines Logo
6:40 a.m. - 11:52 a.m.
SJO
-
YWG
28h 12m
2 stops
C$ 812United Airlines
Thu, 25 Jun - Sat, 11 Jul
United Airlines Logo
2:00 p.m. - 10:11 a.m.
YWG
-
SJO
21h 11m
2 stops
United Airlines Logo
7:55 a.m. - 10:33 p.m.
SJO
-
YWG
37h 38m
2 stops
C$ 837United Airlines
Wed, 29 Jul - Thu, 20 Aug
Multiple Airlines Logo
8:20 p.m. - 11:55 p.m.
YWG
-
SJO
28h 35m
2 stops
Multiple Airlines Logo
4:00 p.m. - 4:25 p.m.
SJO
-
YWG
23h 25m
2 stops
C$ 844Multiple Airlines
Mon, 13 Apr - Tue, 21 Apr
Multiple Airlines Logo
8:10 p.m. - 10:35 p.m.
YWG
-
SJO
27h 25m
1 stop
Multiple Airlines Logo
4:00 p.m. - 11:32 a.m.
SJO
-
YWG
18h 32m
2 stops
C$ 856Multiple Airlines
Wed, 15 Apr - Wed, 22 Apr
United Airlines Logo
7:00 a.m. - 12:21 p.m.
YWG
-
SJO
30h 21m
2 stops
United Airlines Logo
1:25 p.m. - 10:33 p.m.
SJO
-
YWG
32h 08m
2 stops
C$ 862United Airlines
Thu, 30 Jul - Thu, 13 Aug
Multiple Airlines Logo
8:00 a.m. - 11:14 a.m.
YWG
-
SJO
28h 14m
1 stop
Multiple Airlines Logo
4:00 p.m. - 7:25 p.m.
SJO
-
YWG
26h 25m
2 stops
C$ 867Multiple Airlines
Mon, 13 Apr - Tue, 21 Apr

United Airlines flights from Winnipeg to San José

Our best United Airlines deals on Winnipeg to San José flight tickets
United Airlines
30 Jun
YWG7:00 a.m.Winnipeg
28h 11m
2 stops
SJO10:11 a.m.San José Juan Santamaria Intl
6 Jul
SJO12:30 a.m.San José Juan Santamaria Intl
21h 03m
2 stops
YWG10:33 p.m.Winnipeg
C$ 761
United Airlines
25 Jun
YWG7:00 a.m.Winnipeg
16h 39m
2 stops
SJO10:39 p.m.San José Juan Santamaria Intl
10 Jul
SJO1:25 p.m.San José Juan Santamaria Intl
32h 08m
2 stops
YWG10:33 p.m.Winnipeg
C$ 786
United Airlines
25 Jun
YWG7:00 a.m.Winnipeg
16h 39m
2 stops
SJO10:39 p.m.San José Juan Santamaria Intl
11 Jul
SJO6:40 a.m.San José Juan Santamaria Intl
28h 12m
2 stops
YWG11:52 a.m.Winnipeg
C$ 812

Avianca flights from Winnipeg to San José

Our best Avianca deals on Winnipeg to San José flight tickets
Avianca
7 Sep
YWG7:10 p.m.Winnipeg
41h 35m
3 stops
SJO11:45 a.m.San José Juan Santamaria Intl
21 Sep
SJO7:45 p.m.San José Juan Santamaria Intl
24h 27m
2 stops
YWG9:12 p.m.Winnipeg
C$ 1,012
Avianca
29 Mar
YWG2:00 p.m.Winnipeg
21h 11m
2 stops
SJO10:11 a.m.San José Juan Santamaria Intl
5 Apr
SJO1:25 p.m.San José Juan Santamaria Intl
21h 27m
2 stops
YWG11:52 a.m.Winnipeg
C$ 1,460

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 15 March 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

Fri 15/5

7:20 p.m.-10:00 p.m.

1 stop27h 40m

San José Juan Santamaria Intl

Mon 1/6

7:40 a.m.-10:09 a.m.

1 stop25h 29m

C$ 752
Quickest round-trip

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 15/5

5:10 a.m.-8:35 p.m.

2 stops16h 25m

San José Juan Santamaria Intl

Mon 1/6

7:40 a.m.-10:09 a.m.

1 stop25h 29m

C$ 756

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 30/6

7:00 a.m.-10:11 a.m.

2 stops28h 11m

San José Juan Santamaria Intl

Mon 6/7

12:30 a.m.-10:33 p.m.

2 stops21h 03m

C$ 761

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 25/6

7:00 a.m.-10:39 p.m.

2 stops16h 39m

San José Juan Santamaria Intl

Fri 10/7

1:25 p.m.-10:33 p.m.

2 stops32h 08m

C$ 786

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 25/6

7:00 a.m.-10:39 p.m.

2 stops16h 39m

San José Juan Santamaria Intl

Sat 11/7

6:40 a.m.-11:52 a.m.

2 stops28h 12m

C$ 812

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 29/7

2:00 p.m.-10:11 a.m.

2 stops21h 11m

San José Juan Santamaria Intl

Thu 20/8

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

2 stops37h 38m

C$ 837

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 13/4

8:20 p.m.-11:55 p.m.

2 stops28h 35m

San José Juan Santamaria Intl

Tue 21/4

4:00 p.m.-4:25 p.m.

2 stops23h 25m

C$ 844

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 15/4

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

1 stop27h 25m

San José Juan Santamaria Intl

Wed 22/4

4:00 p.m.-11:32 a.m.

2 stops18h 32m

C$ 856

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 30/7

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

2 stops30h 21m

San José Juan Santamaria Intl

Thu 13/8

1:25 p.m.-10:33 p.m.

2 stops32h 08m

C$ 862

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 13/4

8:00 a.m.-11:14 a.m.

1 stop28h 14m

San José Juan Santamaria Intl

Tue 21/4

4:00 p.m.-7:25 p.m.

2 stops26h 25m

C$ 867

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 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, 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$ 793. 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$ 838.

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

16h 39m

Direct flights

None
The fastest flight from Winnipeg to San José takes 16h 39m
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. 16h 39m 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$ 667Free CancellationRating
7.4
9,427 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 1,027Free CancellationRating
7.1
10,801 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
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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