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Cheap flights from Winnipeg to San José from C$ 296

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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJO
27 Aug — 3 Sep1
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 22 August 2025.

Round-trip from

C$ 722

One-way from

C$ 349

Popular in

March

Cheapest in

July

Average price

C$ 1,112
United Airlines
  • United Airlines
  • 14/11-23/11
  • 4 total stops
  • 51h 56m total
  • Winnipeg to San José
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21/10
  • 21/10
  • 3 total stops
  • 49h 10m total
  • Winnipeg to San José
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 133 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 46 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 22 August 2025.

Fri 14/112:20 p.m.YWG - SJO
2 stops30h 19mUnited Airlines
Sun 23/112:20 p.m.SJO - YWG
2 stops21h 37mUnited Airlines
Deal found 20/8C$ 722
Mon 6/109:00 a.m.YWG - SJO
2 stops27h 30mMultiple Airlines
Mon 13/1011:37 a.m.SJO - YWG
2 stops35h 36mMultiple Airlines
Deal found 21/8C$ 728
Fri 31/107:40 a.m.YWG - SJO
2 stops28h 50mMultiple Airlines
Sat 1/1112:55 a.m.SJO - YWG
1 stop10h 40mMultiple Airlines
Deal found 20/8C$ 756
Wed 10/122:20 p.m.YWG - SJO
2 stops30h 19mUnited Airlines
Mon 12/18:45 a.m.SJO - YWG
2 stops26h 54mUnited Airlines
Deal found 20/8C$ 772
Wed 17/99:05 p.m.YWG - SJO
3 stops27h 30mMultiple Airlines
Wed 24/94:45 p.m.SJO - YWG
2 stops30h 28mMultiple Airlines
Deal found 19/8C$ 781
Wed 10/122:20 p.m.YWG - SJO
2 stops30h 19mUnited Airlines
Thu 8/16:30 a.m.SJO - YWG
2 stops29h 09mUnited Airlines
Deal found 20/8C$ 822
Thu 11/125:38 p.m.YWG - SJO
2 stops28h 37mDelta
Thu 8/17:00 a.m.SJO - YWG
2 stops16h 33mDelta
Deal found 20/8C$ 824
Fri 14/1112:10 p.m.YWG - SJO
2 stops47h 17mMultiple Airlines
Sat 22/1112:55 a.m.SJO - YWG
1 stop10h 40mMultiple Airlines
Deal found 20/8C$ 836

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 22 August 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

Fri 14/11

2:20 p.m.-8:39 p.m.

2 stops30h 19m

San José Juan Santamaria Intl

Sun 23/11

2:20 p.m.-11:57 a.m.

2 stops21h 37m

C$ 722

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 31/10

4:00 p.m.-10:41 a.m.

1 stop19h 41m

San José Juan Santamaria Intl

Sun 2/11

4:15 p.m.-11:35 a.m.

2 stops19h 20m

C$ 756

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 17/9

9:05 p.m.-11:35 p.m.

3 stops27h 30m

San José Juan Santamaria Intl

Wed 24/9

4:45 p.m.-12:13 a.m.

2 stops30h 28m

C$ 781

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 14/11

12:10 p.m.-11:27 a.m.

2 stops47h 17m

San José Juan Santamaria Intl

Sat 22/11

12:55 a.m.-11:35 a.m.

1 stop10h 40m

C$ 836

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 18/9

7:00 a.m.-7:37 p.m.

2 stops13h 37m

San José Juan Santamaria Intl

Thu 25/9

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

2 stops25h 01m

C$ 846

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 4/9

6:30 a.m.-11:14 a.m.

3 stops29h 44m

C$ 296

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Wed 3/9

9:05 p.m.-11:14 a.m.

3 stops39h 09m

C$ 304

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 2/9

9:05 p.m.-11:14 a.m.

3 stops39h 09m

C$ 326

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Thu 23/10

9:05 p.m.-11:30 a.m.

3 stops39h 25m

C$ 342

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 21/10

6:30 a.m.-11:30 a.m.

3 stops30h 00m

C$ 347

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/8

Showing 1-10 of 13 results
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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 8 August 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 22 August 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 22 August 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
8,930 reviews
Check prices

Food

6.6

Entertainment

7.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Crew

8.1

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
8,930 reviews
United Airlines
7.4
Good
8,930 reviews
Check prices

Food

6.6

Entertainment

7.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Crew

8.1

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
10,000 reviews
United Airlines
7.4
Good
8,930 reviews
Check prices

Food

6.6

Entertainment

7.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Crew

8.1

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
2,415 reviews
United Airlines
7.4
Good
8,930 reviews
Check prices

Food

6.6

Entertainment

7.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Crew

8.1

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.

  • How long is the flight from Winnipeg to San José, San José Province?

    A quick flight from Winnipeg to San José, San José Province can take about 30h 19m. United Airlines provides one of the quickest options available for as low as C$ 722. There are 4595 km between Winnipeg and San José, San José Province.

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

    Currently priced at C$ 670, 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$ 1,011 and C$ 1,238, respectively. United Airlines is priced at 43% 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 San José?

Book flights to San José if you plan to visit one of these locations
Jacó
Alajuela
Dominical
Manuel Antonio
Monteverde

Browse thousands of different options on Cheapflights for your next trip

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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 22 August 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 670AverageC$ 794FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 1,011AverageC$ 1,447FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
AviancaCheapestC$ 1,238AverageC$ 1,595FlexibilityNo 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.

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