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Cheap flights from Winnipeg to San José from C$ 386

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 6/3. 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.
United Airlines Logo
2:20 p.m. - 11:56 a.m.
YWG
-
SJO
22h 36m
1 stop
United Airlines Logo
1:05 p.m. - 11:57 a.m.
SJO
-
YWG
21h 52m
1 stop
C$ 683United Airlines
mar., 10 mars - mar., 17 mars
United Airlines Logo
2:00 p.m. - 10:11 a.m.
YWG
-
SJO
21h 11m
2 stops
United Airlines Logo
11:13 a.m. - 11:52 a.m.
SJO
-
YWG
23h 39m
2 stops
C$ 684United Airlines
lun., 30 mars - mar., 7 avr.
United Airlines Logo
2:20 p.m. - 9:32 p.m.
YWG
-
SJO
32h 12m
2 stops
United Airlines Logo
5:30 a.m. - 11:57 a.m.
SJO
-
YWG
29h 27m
2 stops
C$ 758United Airlines
mar., 10 mars - mar., 17 mars
Multiple Airlines Logo
7:30 a.m. - 3:20 p.m.
YWG
-
SJO
31h 50m
3 stops
Multiple Airlines Logo
7:05 a.m. - 7:09 p.m.
SJO
-
YWG
35h 04m
2 stops
C$ 766Multiple Airlines
ven., 27 févr. - lun., 9 mars
Multiple Airlines Logo
8:05 p.m. - 11:35 p.m.
YWG
-
SJO
27h 30m
1 stop
Multiple Airlines Logo
12:35 p.m. - 3:30 p.m.
SJO
-
YWG
26h 55m
2 stops
C$ 770Multiple Airlines
mer., 18 févr. - mer., 25 févr.
Multiple Airlines Logo
7:30 a.m. - 1:15 p.m.
YWG
-
SJO
29h 45m
1 stop
Multiple Airlines Logo
11:35 a.m. - 11:32 a.m.
SJO
-
YWG
22h 57m
2 stops
C$ 796Multiple Airlines
ven., 27 févr. - lun., 9 mars
Multiple Airlines Logo
7:30 a.m. - 12:22 p.m.
YWG
-
SJO
28h 52m
2 stops
Multiple Airlines Logo
7:05 a.m. - 7:09 p.m.
SJO
-
YWG
35h 04m
2 stops
C$ 809Multiple Airlines
ven., 27 févr. - lun., 9 mars
Multiple Airlines Logo
8:00 a.m. - 11:19 a.m.
YWG
-
SJO
28h 19m
1 stop
Multiple Airlines Logo
12:24 p.m. - 11:32 a.m.
SJO
-
YWG
22h 08m
2 stops
C$ 813Multiple Airlines
lun., 30 mars - mar., 7 avr.
Multiple Airlines Logo
7:30 a.m. - 3:20 p.m.
YWG
-
SJO
31h 50m
3 stops
Multiple Airlines Logo
5:30 a.m. - 6:05 p.m.
SJO
-
YWG
35h 35m
3 stops
C$ 814Multiple Airlines
ven., 27 févr. - lun., 9 mars
United Airlines Logo
2:20 p.m. - 6:16 p.m.
YWG
-
SJO
27h 56m
2 stops
United Airlines Logo
8:45 a.m. - 11:57 a.m.
SJO
-
YWG
27h 12m
2 stops
C$ 821United Airlines
mer., 18 févr. - mer., 25 févr.

United Airlines flights from Winnipeg to San José

Our best United Airlines deals on Winnipeg to San José flight tickets
United Airlines
30 Mar
YWG2:00 p.m.Winnipeg
21h 11m
2 stops
SJO10:11 a.m.San José Juan Santamaria Intl
7 Apr
SJO11:13 a.m.San José Juan Santamaria Intl
23h 39m
2 stops
YWG11:52 a.m.Winnipeg
C$ 684
United Airlines
18 Feb
YWG2:20 p.m.Winnipeg
27h 56m
2 stops
SJO6:16 p.m.San José Juan Santamaria Intl
25 Feb
SJO8:45 a.m.San José Juan Santamaria Intl
27h 12m
2 stops
YWG11:57 a.m.Winnipeg
C$ 821
United Airlines
10 Feb
YWG2:20 p.m.Winnipeg
30h 19m
2 stops
SJO8:39 p.m.San José Juan Santamaria Intl
20 Feb
SJO8:45 a.m.San José Juan Santamaria Intl
27h 12m
2 stops
YWG11:57 a.m.Winnipeg
C$ 850

Air Canada flights from Winnipeg to San José

Our best Air Canada deals on Winnipeg to San José flight tickets
Air Canada
26 Jan
YWG5:30 p.m.Winnipeg
30h 35m
1 stop
SJO12:05 a.m.San José Juan Santamaria Intl
4 Feb
SJO8:50 a.m.San José Juan Santamaria Intl
25h 25m
1 stop
YWG10:15 a.m.Winnipeg
C$ 1,016
Air Canada
26 Jan
YWG7:05 p.m.Winnipeg
28h 10m
2 stops
SJO11:15 p.m.San José Juan Santamaria Intl
4 Feb
SJO8:50 a.m.San José Juan Santamaria Intl
11h 38m
2 stops
YWG8:28 p.m.Winnipeg
C$ 1,019
Air Canada
26 Jan
YWG7:05 p.m.Winnipeg
28h 10m
2 stops
SJO11:15 p.m.San José Juan Santamaria Intl
4 Feb
SJO8:50 a.m.San José Juan Santamaria Intl
11h 38m
2 stops
YWG8:28 p.m.Winnipeg
C$ 1,022

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 21 janvier 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

mar. 10/3

2:20 p.m.-11:56 a.m.

1 stop22h 36m

San José Juan Santamaria Intl

mar. 17/3

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

1 stop21h 52m

C$ 683

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

lun. 30/3

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

2 stops21h 11m

San José Juan Santamaria Intl

mar. 7/4

11:13 a.m.-11:52 a.m.

2 stops23h 39m

C$ 684

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

mar. 10/3

2:20 p.m.-9:32 p.m.

2 stops32h 12m

San José Juan Santamaria Intl

mar. 17/3

5:30 a.m.-11:57 a.m.

2 stops29h 27m

C$ 758

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

ven. 27/2

7:30 a.m.-3:20 p.m.

3 stops31h 50m

San José Juan Santamaria Intl

lun. 9/3

7:05 a.m.-7:09 p.m.

2 stops35h 04m

C$ 766

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

mer. 18/2

8:05 p.m.-11:35 p.m.

1 stop27h 30m

San José Juan Santamaria Intl

mer. 25/2

12:35 p.m.-3:30 p.m.

2 stops26h 55m

C$ 770

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

ven. 27/2

7:30 a.m.-1:15 p.m.

1 stop29h 45m

San José Juan Santamaria Intl

lun. 9/3

11:35 a.m.-11:32 a.m.

2 stops22h 57m

C$ 796

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

ven. 27/2

7:30 a.m.-12:22 p.m.

2 stops28h 52m

San José Juan Santamaria Intl

lun. 9/3

7:05 a.m.-7:09 p.m.

2 stops35h 04m

C$ 809

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

lun. 30/3

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

1 stop28h 19m

San José Juan Santamaria Intl

mar. 7/4

12:24 p.m.-11:32 a.m.

2 stops22h 08m

C$ 813

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

ven. 27/2

7:30 a.m.-3:20 p.m.

3 stops31h 50m

San José Juan Santamaria Intl

lun. 9/3

5:30 a.m.-6:05 p.m.

3 stops35h 35m

C$ 814

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

mer. 18/2

2:20 p.m.-6:16 p.m.

2 stops27h 56m

San José Juan Santamaria Intl

mer. 25/2

8:45 a.m.-11:57 a.m.

2 stops27h 12m

C$ 821

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 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

22h 36m

Direct flights

None
The fastest flight from Winnipeg to San José takes 22h 36m
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. 22h 36m 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$ 669Free CancellationRating
7.4
9,191 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 1,047Free CancellationRating
7.1
10,646 reviews
Search Air Canada flights
AviancaPriceFrom C$ 1,232Free CancellationRating
6.6
2,496 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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