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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 19/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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.
Multiple Airlines Logo
8:20 p.m. - 3:20 p.m.
YWG
-
SJO
19h 00m
2 stops
Multiple Airlines Logo
7:05 a.m. - 7:09 p.m.
SJO
-
YWG
35h 04m
2 stops
C$ 696Multiple Airlines
Tue, 3 Mar - Wed, 11 Mar
United Airlines Logo
8:30 a.m. - 10:11 a.m.
YWG
-
SJO
26h 41m
2 stops
United Airlines Logo
11:13 a.m. - 10:24 p.m.
SJO
-
YWG
34h 11m
2 stops
C$ 705United Airlines
Mon, 27 Jul - Thu, 6 Aug
United Airlines Logo
2:00 p.m. - 12:21 p.m.
YWG
-
SJO
23h 21m
2 stops
United Airlines Logo
12:30 a.m. - 8:48 p.m.
SJO
-
YWG
19h 18m
2 stops
C$ 706United Airlines
Mon, 18 May - Tue, 2 Jun
Multiple Airlines Logo
8:20 p.m. - 3:20 p.m.
YWG
-
SJO
19h 00m
2 stops
Multiple Airlines Logo
7:05 a.m. - 11:32 a.m.
SJO
-
YWG
27h 27m
2 stops
C$ 709Multiple Airlines
Tue, 3 Mar - Mon, 9 Mar
Multiple Airlines Logo
12:20 p.m. - 11:35 p.m.
YWG
-
SJO
11h 15m
1 stop
Multiple Airlines Logo
11:35 a.m. - 7:35 p.m.
SJO
-
YWG
31h 00m
2 stops
C$ 710Multiple Airlines
Tue, 3 Mar - Mon, 9 Mar
Multiple Airlines Logo
8:20 p.m. - 3:20 p.m.
YWG
-
SJO
19h 00m
2 stops
Multiple Airlines Logo
12:31 p.m. - 7:35 p.m.
SJO
-
YWG
30h 04m
3 stops
C$ 716Multiple Airlines
Tue, 3 Mar - Mon, 9 Mar
Multiple Airlines Logo
5:10 p.m. - 11:55 p.m.
YWG
-
SJO
31h 45m
2 stops
Multiple Airlines Logo
12:31 p.m. - 3:25 p.m.
SJO
-
YWG
25h 54m
3 stops
C$ 718Multiple Airlines
Sat, 18 Apr - Sat, 25 Apr
Multiple Airlines Logo
12:20 p.m. - 12:22 p.m.
YWG
-
SJO
24h 02m
3 stops
Multiple Airlines Logo
12:31 p.m. - 7:35 p.m.
SJO
-
YWG
30h 04m
3 stops
C$ 727Multiple Airlines
Tue, 3 Mar - Mon, 9 Mar
United Airlines Logo
2:00 p.m. - 12:21 p.m.
YWG
-
SJO
23h 21m
2 stops
United Airlines Logo
7:55 a.m. - 8:57 p.m.
SJO
-
YWG
36h 02m
2 stops
C$ 729United Airlines
Mon, 11 May - Mon, 18 May
United Airlines Logo
8:45 a.m. - 5:30 a.m.
YWG
-
SJO
21h 45m
2 stops
United Airlines Logo
12:30 a.m. - 8:48 p.m.
SJO
-
YWG
19h 18m
2 stops
C$ 731United Airlines
Fri, 15 May - Thu, 28 May

United Airlines flights from Winnipeg to San José

Our best United Airlines deals on Winnipeg to San José flight tickets
United Airlines
27 Jul
YWG8:30 a.m.Winnipeg
26h 41m
2 stops
SJO10:11 a.m.San José Juan Santamaria Intl
6 Aug
SJO11:13 a.m.San José Juan Santamaria Intl
34h 11m
2 stops
YWG10:24 p.m.Winnipeg
C$ 705
United Airlines
18 May
YWG2:00 p.m.Winnipeg
23h 21m
2 stops
SJO12:21 p.m.San José Juan Santamaria Intl
2 Jun
SJO12:30 a.m.San José Juan Santamaria Intl
19h 18m
2 stops
YWG8:48 p.m.Winnipeg
C$ 706
United Airlines
11 May
YWG2:00 p.m.Winnipeg
23h 21m
2 stops
SJO12:21 p.m.San José Juan Santamaria Intl
18 May
SJO7:55 a.m.San José Juan Santamaria Intl
36h 02m
2 stops
YWG8:57 p.m.Winnipeg
C$ 729

Air Canada flights from Winnipeg to San José

Our best Air Canada deals on Winnipeg to San José flight tickets
Air Canada
17 May
YWG5:10 p.m.Winnipeg
29h 50m
1 stop
SJO10:00 p.m.San José Juan Santamaria Intl
29 May
SJO8:00 a.m.San José Juan Santamaria Intl
26h 08m
1 stop
YWG11:08 a.m.Winnipeg
C$ 989
Air Canada
18 May
YWG12:15 p.m.Winnipeg
10h 45m
1 stop
SJO10:00 p.m.San José Juan Santamaria Intl
31 May
SJO8:00 a.m.San José Juan Santamaria Intl
25h 03m
1 stop
YWG10:03 a.m.Winnipeg
C$ 1,040
Air Canada
17 Feb
YWG6:00 a.m.Winnipeg
17h 15m
2 stops
SJO11:15 p.m.San José Juan Santamaria Intl
18 Feb
SJO8:50 a.m.San José Juan Santamaria Intl
25h 25m
1 stop
YWG10:15 a.m.Winnipeg
C$ 1,285

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 5 February 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

Tue 3/3

8:20 p.m.-3:20 p.m.

2 stops19h 00m

San José Juan Santamaria Intl

Wed 11/3

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

2 stops35h 04m

C$ 696

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 27/7

8:30 a.m.-10:11 a.m.

2 stops26h 41m

San José Juan Santamaria Intl

Thu 6/8

11:13 a.m.-10:24 p.m.

2 stops34h 11m

C$ 705

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 18/5

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

2 stops23h 21m

San José Juan Santamaria Intl

Tue 2/6

12:30 a.m.-8:48 p.m.

2 stops19h 18m

C$ 706

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 3/3

8:20 p.m.-3:20 p.m.

2 stops19h 00m

San José Juan Santamaria Intl

Mon 9/3

7:05 a.m.-11:32 a.m.

2 stops27h 27m

C$ 709

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 3/3

12:20 p.m.-11:35 p.m.

1 stop11h 15m

San José Juan Santamaria Intl

Mon 9/3

11:35 a.m.-7:35 p.m.

2 stops31h 00m

C$ 710

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 3/3

8:20 p.m.-3:20 p.m.

2 stops19h 00m

San José Juan Santamaria Intl

Mon 9/3

12:31 p.m.-7:35 p.m.

3 stops30h 04m

C$ 716

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 18/4

5:10 p.m.-11:55 p.m.

2 stops31h 45m

San José Juan Santamaria Intl

Sat 25/4

12:31 p.m.-3:25 p.m.

3 stops25h 54m

C$ 718

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 3/3

12:20 p.m.-12:22 p.m.

3 stops24h 02m

San José Juan Santamaria Intl

Mon 9/3

12:31 p.m.-7:35 p.m.

3 stops30h 04m

C$ 727

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 11/5

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

2 stops23h 21m

San José Juan Santamaria Intl

Mon 18/5

7:55 a.m.-8:57 p.m.

2 stops36h 02m

C$ 729

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 15/5

8:45 a.m.-5:30 a.m.

2 stops21h 45m

San José Juan Santamaria Intl

Thu 28/5

12:30 a.m.-8:48 p.m.

2 stops19h 18m

C$ 731

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 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$ 810. 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$ 836.

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$ 1,130 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$ 840 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

10h 50m

Direct flights

None
The fastest flight from Winnipeg to San José takes 10h 50m
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. 10h 50m 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$ 662Free CancellationRating
7.4
9,240 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 1,036Free CancellationRating
7.1
10,694 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.

An easier way to manage your San José trip

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