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Cheap flights from Winnipeg to San José from C$ 308

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 27/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJO
8 jul. — 15 jul.1
1 adult

Cheapflights Tip: The best prices from Winnipeg to San José Juan Santamaria Intl are usually found in July or September, booked 61 days in advance, depart on a Tuesday or Friday and return on a Monday

Cheap flight deals from Winnipeg to San José

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to San José (SJO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 3 julio 2025.

Round-trip from

C$ 700

One-way from

C$ 382

Popular in

March

Cheapest in

July

Average price

C$ 788
30/8-3/9
  • 30/8-3/9
  • 3 total stops
  • 53h 26m total
  • Winnipeg to San José
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15/8
  • 15/8
  • 3 total stops
  • 19h 58m total
  • Winnipeg to San José
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 170 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 51 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Winnipeg to San José

Cheapest flights from Winnipeg to San José
Explore the most affordable flight options available from Winnipeg to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 3 julio 2025.

jue. 23/104:25 p.m.YWG - SJO
2 stops45h 01mUnited Airlines
mié. 12/118:45 a.m.SJO - YWG
2 stops27h 12mUnited Airlines
Deal found 3/7C$ 692
sáb. 30/89:10 a.m.YWG - SJO
1 stop26h 22mMultiple Airlines
mié. 3/912:18 p.m.SJO - YWG
2 stops27h 04mMultiple Airlines
Deal found 2/7C$ 700
vie. 28/1111:05 a.m.YWG - SJO
1 stop13h 00mAir Canada
mar. 2/128:35 a.m.SJO - YWG
1 stop10h 49mAir Canada
Deal found 2/7C$ 991
mar. 8/76:35 p.m.YWG - SJO
2 stops17h 40mAvianca
vie. 11/77:45 p.m.SJO - YWG
2 stops19h 28mAvianca
Deal found 1/7C$ 1,289

Cheapflights 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, Cheapflights users made 629,999 searches. Data last updated 3 julio 2025.
Use the filters below to find and compare flights from Winnipeg to San José that are best for you.

Fly from

Winnipeg

Fly to

San José

Route

Depart

Return

Price

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

jue. 23/10

4:25 p.m.-12:26 p.m.

2 stops45h 01m

San José Juan Santamaria Intl

mié. 12/11

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

2 stops27h 12m

C$ 692

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

sáb. 30/8

9:10 a.m.-10:32 a.m.

1 stop26h 22m

San José Juan Santamaria Intl

mié. 3/9

12:18 p.m.-4:22 p.m.

2 stops27h 04m

C$ 700

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

vie. 28/11

7:05 p.m.-11:15 p.m.

2 stops28h 10m

San José Juan Santamaria Intl

mar. 2/12

8:35 a.m.-9:44 p.m.

1 stop13h 09m

C$ 991

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

jue. 17/7

5:10 p.m.-11:15 a.m.

2 stops19h 05m

San José Juan Santamaria Intl

vie. 31/10

2:15 a.m.-10:49 a.m.

2 stops31h 34m

C$ 1,586

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

lun. 27/10

7:30 a.m.-11:18 a.m.

3 stops28h 48m

C$ 308

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

mar. 21/10

12:40 p.m.-11:48 a.m.

2 stops24h 08m

C$ 432

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

lun. 27/10

1:30 p.m.-11:05 p.m.

1 stop10h 35m

C$ 496

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/7

Best time to book a flight from Winnipeg to San José

Have a flexible travel schedule? Discover the best time to fly to San José from Winnipeg with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to San José

How far ahead should I book a flight from Winnipeg to San José, San José Province?

Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to San José. Price data was last updated on 27 June 2025.

The best time to book flights from Winnipeg to San José, San José Province is 61 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Winnipeg to San José, San José Province?

Currently, September is the cheapest month in which you can book a flight from Winnipeg to San José, San José Province (average of C$ 486). Flying from Winnipeg to San José, San José Province in December is currently the most expensive (average of C$ 683). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YWG to SJO?

Find hourly flight availability from Winnipeg to San José. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 3 julio 2025.

A simple way to save on the total cost of your ticket is to fly from Winnipeg to San José, San José Province at noon. If you’re flexible enough to do this you can expect to save up to 43% on your trip compared to booking a flight in the morning.

Reviews of airlines servicing San José

Get insights into the airlines that provide service to San José. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San José. Reviews last updated 3 julio 2025.
See what other customers who have flown with United Airlines,Air Canada, andAvianca from Winnipeg to San José have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,861 reviews
Check prices

Overall

7.4

Comfort

7.3

Food

6.6

Crew

8.1

Boarding

7.7

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2024

YVR - SFO

It was a good experience. The flight took 45 minutes longer to fly and all passengers had to wait inside the plane till the technical issue was fixed. Overall it was a good experience.
United Airlines
7.4
Good
8,861 reviews
United Airlines
7.4
Good
8,861 reviews
Check prices

Overall

7.4

Comfort

7.3

Food

6.6

Crew

8.1

Boarding

7.7

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2024

YVR - SFO

It was a good experience. The flight took 45 minutes longer to fly and all passengers had to wait inside the plane till the technical issue was fixed. Overall it was a good experience.
Air Canada
7.1
Good
9,681 reviews
United Airlines
7.4
Good
8,861 reviews
Check prices

Overall

7.4

Comfort

7.3

Food

6.6

Crew

8.1

Boarding

7.7

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2024

YVR - SFO

It was a good experience. The flight took 45 minutes longer to fly and all passengers had to wait inside the plane till the technical issue was fixed. Overall it was a good experience.
Avianca
6.7
Okay
2,363 reviews
United Airlines
7.4
Good
8,861 reviews
Check prices

Overall

7.4

Comfort

7.3

Food

6.6

Crew

8.1

Boarding

7.7

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2024

YVR - SFO

It was a good experience. The flight took 45 minutes longer to fly and all passengers had to wait inside the plane till the technical issue was fixed. Overall it was a good experience.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to San José. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines flying from Winnipeg to San José, San José Province round-trip?

    Currently priced at C$ 816, United Airlines will fly you from Winnipeg to San José, San José Province and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Avianca and Air Canada - these airlines can fly you to your destination from C$ 1,289 and C$ 1,577, respectively. United Airlines is priced at 29% lower than the current average price of a flight leaving 3 months from now.

  • Can I find deals for flights from Winnipeg to San José that include hotel bookings?

    Yes. In addition to deals on Winnipeg to San José flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to San José?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to San José.

  • Can I find deals for business class flights from Winnipeg to San José?

    Yes. Cheapflights offers flight deals from Winnipeg to San José by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Winnipeg to San José, San José Province?

    Currently, September is the cheapest month in which you can book a flight from Winnipeg to San José, San José Province (average of C$ 486). Flying from Winnipeg to San José, San José Province in December is currently the most expensive (average of C$ 683). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Travelling to a place near Winnipeg?

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Alternative routes for Winnipeg to San José

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Winnipeg to Liberia flights

Top 3 airlines flying from Winnipeg to San José

Discover the top 3 airlines that operate flights from Winnipeg to San José. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 3 julio 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 655AverageC$ 778FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 1,041AverageC$ 1,449FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
AviancaCheapestC$ 1,318AverageC$ 1,565FlexibilityNo cancel feeOn-time71%
Search Avianca flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Winnipeg to San José?

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Why should you use Cheapflights to find cheap flight tickets from Winnipeg to San José?

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Can Cheapflights find flights from Winnipeg to San José with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Winnipeg to San José flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Winnipeg to San José become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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