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Cheap flights from Winnipeg to San José from C$ 299

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 28/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJO
4 May — 11 May1
1 adult

Cheapflights Tip: The best prices from Winnipeg to San José Juan Santamaria Intl are usually found in August or September, booked 4 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 29 April 2025.

Round-trip from

C$ 672

One-way from

C$ 299

Popular in

December

Cheapest in

August

Average price

C$ 1,078
27/5-3/6
  • 27/5-3/6
  • 4 total stops
  • 51h 02m total
  • Winnipeg to San José
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28/5
  • 28/5
  • 2 total stops
  • 24h 02m total
  • Winnipeg to San José
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Highest demand for flights based on searches. 10% potential increase in price (C$ 208 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease (C$ 72 potential savings vs. average RT price).
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Average for round-trip flights in April 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 29 April 2025.

Wed 6/812:15 p.m.YWG - SJO
3 stops19h 58mMultiple Airlines
Mon 18/82:42 p.m.SJO - YWG
3 stops25h 59mMultiple Airlines
Deal found 27/4C$ 664
Tue 19/87:00 a.m.YWG - SJO
2 stops30h 26mUnited Airlines
Tue 26/81:30 p.m.SJO - YWG
2 stops25h 01mUnited Airlines
Deal found 28/4C$ 671
Wed 11/611:10 a.m.YWG - SJO
1 stop10h 15mAir Canada
Thu 26/67:55 a.m.SJO - YWG
1 stop25h 24mAir Canada
Deal found 27/4C$ 1,146
Wed 28/55:00 a.m.YWG - SJO
2 stops19h 35mAvianca
Tue 3/61:55 a.m.SJO - YWG
2 stops30h 45mAvianca
Deal found 28/4C$ 1,735

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 29 April 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

Tue 19/8

7:00 a.m.-12:26 p.m.

2 stops30h 26m

San José Juan Santamaria Intl

Tue 26/8

1:30 p.m.-3:31 p.m.

2 stops25h 01m

C$ 671

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 27/5

11:25 a.m.-10:27 a.m.

2 stops24h 02m

San José Juan Santamaria Intl

Tue 3/6

12:28 p.m.-4:28 p.m.

2 stops27h 00m

C$ 672

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sat 18/10

7:40 a.m.-10:55 p.m.

1 stop16h 15m

San José Juan Santamaria Intl

Sat 1/11

7:55 a.m.-6:28 p.m.

1 stop9h 33m

C$ 1,217

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 28/5

5:00 a.m.-11:35 p.m.

2 stops19h 35m

San José Juan Santamaria Intl

Tue 3/6

1:55 a.m.-9:40 a.m.

2 stops30h 45m

C$ 1,735

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 28/5

11:25 a.m.-10:27 a.m.

2 stops24h 02m

C$ 299

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 28/5

4:30 p.m.-10:50 p.m.

1 stop31h 20m

C$ 581

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/4

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 25 April 2025.

The best time to book flights from Winnipeg to San José, San José Province is 2 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 29 April 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.

Rainfall in San José by month

Plan your trip to San José by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San José, San José Province ranges from 0.0 - 300.0 mm per month. September is typically the wettest month, when rainfall can reach 300.0 mm. February is typically the driest time to visit San José, San José Province when rainfall is around 0.0 mm.

Temperature in San José by month

Plan your trip to San José by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San José, San José Province, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 21.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 18.0 C).

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 29 April 2025.
Delta
8.0
Very good
7,929 reviews
Check prices

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Food

7.3

Reviews

1 / 20
4.0
Okay

Peter,Oct 2023

MSP - GEG

The amount of carry on is put of control. We were in group 3 boarding and there was no room in upper storage for our 1 bag (between 2 people) Just because we can’t afford to up grade our seats… $2000 more. We get penaltized. Make us feel less than
Delta
8.0
Very good
7,929 reviews
Delta
8.0
Very good
7,929 reviews
Check prices

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Food

7.3

Reviews

1 / 20
4.0
Okay

Peter,Oct 2023

MSP - GEG

The amount of carry on is put of control. We were in group 3 boarding and there was no room in upper storage for our 1 bag (between 2 people) Just because we can’t afford to up grade our seats… $2000 more. We get penaltized. Make us feel less than
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,929 reviews
Check prices

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Food

7.3

Reviews

1 / 20
4.0
Okay

Peter,Oct 2023

MSP - GEG

The amount of carry on is put of control. We were in group 3 boarding and there was no room in upper storage for our 1 bag (between 2 people) Just because we can’t afford to up grade our seats… $2000 more. We get penaltized. Make us feel less than
Air Canada
7.0
Good
9,228 reviews
Delta
8.0
Very good
7,929 reviews
Check prices

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Food

7.3

Reviews

1 / 20
4.0
Okay

Peter,Oct 2023

MSP - GEG

The amount of carry on is put of control. We were in group 3 boarding and there was no room in upper storage for our 1 bag (between 2 people) Just because we can’t afford to up grade our seats… $2000 more. We get penaltized. Make us feel less than
Avianca
6.7
Okay
2,317 reviews
Delta
8.0
Very good
7,929 reviews
Check prices

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.9

Food

7.3

Reviews

1 / 20
4.0
Okay

Peter,Oct 2023

MSP - GEG

The amount of carry on is put of control. We were in group 3 boarding and there was no room in upper storage for our 1 bag (between 2 people) Just because we can’t afford to up grade our seats… $2000 more. We get penaltized. Make us feel less than

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$ 820, 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 Air Canada and Avianca - these airlines can fly you to your destination from C$ 1,221 and C$ 1,735, respectively. United Airlines is priced at 34% 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?

Book flights to Winnipeg if you plan to visit one of these locations
Jacó
Alajuela
Dominical
Monteverde

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Alternative routes for Winnipeg to San José

See prices for flight routes from nearby airports that may be better suited for you.
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 29 April 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 665AverageC$ 815FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 1,027AverageC$ 1,495FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
AviancaCheapestC$ 1,116AverageC$ 1,592FlexibilityNo cancel feeOn-time71%
Search Avianca flights

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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.

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