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Cheap flights from Winnipeg to San José from C$ 300

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 1/2. 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.
Multiple Airlines Logo
8:00 a.m. - 12:22 p.m.
YWG
-
SJO
28h 22m1 stop
Multiple Airlines Logo
1:30 p.m. - 12:42 a.m.
SJO
-
YWG
35h 12m2 stops
C$ 573Multiple Airlines
Mon, 12 Jan - Mon, 26 Jan
Multiple Airlines Logo
8:00 a.m. - 12:22 p.m.
YWG
-
SJO
28h 22m1 stop
Multiple Airlines Logo
4:15 p.m. - 7:35 p.m.
SJO
-
YWG
26h 20m2 stops
C$ 637Multiple Airlines
Mon, 2 Mar - Tue, 10 Mar
Multiple Airlines Logo
8:00 a.m. - 12:22 p.m.
YWG
-
SJO
28h 22m1 stop
Multiple Airlines Logo
9:45 a.m. - 11:32 a.m.
SJO
-
YWG
24h 47m2 stops
C$ 638Multiple Airlines
Mon, 2 Mar - Wed, 11 Mar
Multiple Airlines Logo
8:00 a.m. - 12:22 p.m.
YWG
-
SJO
28h 22m1 stop
Multiple Airlines Logo
4:15 p.m. - 3:09 p.m.
SJO
-
YWG
21h 54m3 stops
C$ 660Multiple Airlines
Mon, 2 Mar - Tue, 10 Mar
Multiple Airlines Logo
10:55 a.m. - 8:25 p.m.
YWG
-
SJO
33h 30m3 stops
Multiple Airlines Logo
7:30 a.m. - 6:05 p.m.
SJO
-
YWG
33h 35m3 stops
C$ 661Multiple Airlines
Mon, 2 Mar - Tue, 10 Mar
Multiple Airlines Logo
12:20 p.m. - 11:35 p.m.
YWG
-
SJO
11h 15m1 stop
Multiple Airlines Logo
1:30 p.m. - 3:30 p.m.
SJO
-
YWG
26h 00m2 stops
C$ 667Multiple Airlines
Thu, 22 Jan - Thu, 5 Feb
United Airlines Logo
2:20 p.m. - 12:56 p.m.
YWG
-
SJO
22h 36m1 stop
United Airlines Logo
5:30 a.m. - 11:57 a.m.
SJO
-
YWG
29h 27m2 stops
C$ 671United Airlines
Sun, 1 Mar - Wed, 11 Mar
Multiple Airlines Logo
12:10 p.m. - 12:22 p.m.
YWG
-
SJO
24h 12m2 stops
Multiple Airlines Logo
7:22 a.m. - 11:47 p.m.
SJO
-
YWG
40h 25m3 stops
C$ 688Multiple Airlines
Sun, 1 Feb - Sat, 28 Feb
Multiple Airlines Logo
10:55 a.m. - 8:25 p.m.
YWG
-
SJO
33h 30m3 stops
Multiple Airlines Logo
7:30 a.m. - 11:32 a.m.
SJO
-
YWG
27h 02m2 stops
C$ 690Multiple Airlines
Mon, 2 Mar - Tue, 10 Mar
United Airlines Logo
2:20 p.m. - 12:56 p.m.
YWG
-
SJO
22h 36m1 stop
United Airlines Logo
11:35 a.m. - 11:57 a.m.
SJO
-
YWG
23h 22m2 stops
C$ 696United Airlines
Sat, 28 Feb - Wed, 11 Mar

United Airlines flights from Winnipeg to San José

Our best United Airlines deals on Winnipeg to San José flight tickets
United Airlines
1 Mar
YWG2:20 p.m.Winnipeg
27h 56m
2 stops
SJO6:16 p.m.San José Juan Santamaria Intl
10 Mar
SJO1:05 p.m.San José Juan Santamaria Intl
21h 52m
1 stop
YWG11:57 a.m.Winnipeg
C$ 671
Find similar
United Airlines
28 Feb
YWG2:20 p.m.Winnipeg
22h 36m
1 stop
SJO12:56 p.m.San José Juan Santamaria Intl
11 Mar
SJO11:35 a.m.San José Juan Santamaria Intl
23h 22m
2 stops
YWG11:57 a.m.Winnipeg
C$ 696
Find similar
United Airlines
28 Feb
YWG2:20 p.m.Winnipeg
16h 05m
2 stops
SJO6:25 a.m.San José Juan Santamaria Intl
9 Mar
SJO1:20 p.m.San José Juan Santamaria Intl
21h 37m
2 stops
YWG11:57 a.m.Winnipeg
C$ 721
Find similar

Avianca flights from Winnipeg to San José

Our best Avianca deals on Winnipeg to San José flight tickets
Avianca
28 Feb
YWG5:30 p.m.Winnipeg
42h 15m
3 stops
SJO11:45 a.m.San José Juan Santamaria Intl
12 Mar
SJO5:00 a.m.San José Juan Santamaria Intl
27h 49m
2 stops
YWG9:49 a.m.Winnipeg
C$ 919
Find similar
Avianca
28 Feb
YWG5:30 p.m.Winnipeg
30h 10m
2 stops
SJO11:40 p.m.San José Juan Santamaria Intl
11 Mar
SJO12:40 p.m.San José Juan Santamaria Intl
44h 09m
3 stops
YWG9:49 a.m.Winnipeg
C$ 929
Find similar

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 December 2025.
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

Mon 12/1

8:00 a.m.-12:22 p.m.

1 stop28h 22m

San José Juan Santamaria Intl

Mon 26/1

1:30 p.m.-12:42 a.m.

2 stops35h 12m

C$ 573

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 2/3

8:00 a.m.-12:22 p.m.

1 stop28h 22m

San José Juan Santamaria Intl

Tue 10/3

4:15 p.m.-7:35 p.m.

2 stops26h 20m

C$ 637

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 2/3

8:00 a.m.-12:22 p.m.

1 stop28h 22m

San José Juan Santamaria Intl

Wed 11/3

9:45 a.m.-11:32 a.m.

2 stops24h 47m

C$ 638

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 2/3

8:00 a.m.-12:22 p.m.

1 stop28h 22m

San José Juan Santamaria Intl

Tue 10/3

4:15 p.m.-3:09 p.m.

3 stops21h 54m

C$ 660

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 2/3

10:55 a.m.-8:25 p.m.

3 stops33h 30m

San José Juan Santamaria Intl

Tue 10/3

7:30 a.m.-6:05 p.m.

3 stops33h 35m

C$ 661

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 22/1

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

1 stop11h 15m

San José Juan Santamaria Intl

Thu 5/2

1:30 p.m.-3:30 p.m.

2 stops26h 00m

C$ 667

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 1/3

2:20 p.m.-12:56 p.m.

1 stop22h 36m

San José Juan Santamaria Intl

Wed 11/3

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

2 stops29h 27m

C$ 671

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 1/2

12:10 p.m.-12:22 p.m.

2 stops24h 12m

San José Juan Santamaria Intl

Sat 28/2

7:22 a.m.-11:47 p.m.

3 stops40h 25m

C$ 688

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Mon 2/3

10:55 a.m.-8:25 p.m.

3 stops33h 30m

San José Juan Santamaria Intl

Tue 10/3

7:30 a.m.-11:32 a.m.

2 stops27h 02m

C$ 690

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 28/2

2:20 p.m.-12:56 p.m.

1 stop22h 36m

San José Juan Santamaria Intl

Wed 11/3

11:35 a.m.-11:57 a.m.

2 stops23h 22m

C$ 696

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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$ 816. 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$ 842.

What is the cheapest day to depart on your flight to San José?

The cheapest day to depart from Winnipeg to San José is on a Tuesday. Travellers who choose to depart for San José on a Tuesday will often find tickets for as low as C$ 1,039. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around C$ 1,348. These prices are subject to change though, so be sure to set up a Price Alert for flights to San José.

What is the cheapest time of day to depart on your flight to San José?

Flying to San José from Winnipeg at noon is the least expensive time of day to depart. momondo users have found prices as low as C$ 777 when looking at flights departing at noon. In contrast, the most expensive time of day to depart to San José is in the morning when prices are around C$ 1,354.

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$ 1,132 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$ 864 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

17h 20m

Direct flights

None
The fastest flight from Winnipeg to San José takes 17h 20m
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. 17h 20m 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$ 656Free CancellationRating
7.4
9,093 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 1,031Free CancellationRating
7.1
10,534 reviews
Search Air Canada flights
AviancaPriceFrom C$ 1,228Free CancellationRating
6.6
2,490 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
Monteverde
Dominical
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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