$364 Cheap Flights from San José (SJO) to Winnipeg (YWG)

View $364 flight on Fri, Oct 24, 2025Opens in a new window

Popular airlines from Juan Santamaria Intl. Airport (SJO) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)

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Cheap Flights from San José to Winnipeg (SJO-YWG)

Prices were available within the past 7 days and start at $364 for one-way flights and $630 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Fri, Dec 12 - Mon, Jan 12
SJO
San José
YWG
Winnipeg
$630 Roundtrip, found 1 day ago
$630
Roundtrip
found 1 day ago
Select United flight, departing Fri, Dec 12 from San José to Winnipeg, returning Mon, Jan 12, priced at $630 found 1 day ago
United
Wed, Jan 14 - Sun, Jan 25
SJO
San José
YWG
Winnipeg
$648 Roundtrip, found 2 days ago
$648
Roundtrip
found 2 days ago
Select United flight, departing Wed, Jan 14 from San José to Winnipeg, returning Sun, Jan 25, priced at $648 found 2 days ago
United
Wed, Apr 15 - Fri, Apr 24
SJO
San José
YWG
Winnipeg
$652 Roundtrip, found 2 days ago
$652
Roundtrip
found 2 days ago
Select United flight, departing Wed, Apr 15 from San José to Winnipeg, returning Fri, Apr 24, priced at $652 found 2 days ago
United
Fri, Dec 12 - Mon, Jan 12
SJO
San José
YWG
Winnipeg
$653 Roundtrip, found 1 day ago
$653
Roundtrip
found 1 day ago
Select United flight, departing Fri, Dec 12 from San José to Winnipeg, returning Mon, Jan 12, priced at $653 found 1 day ago
United
Mon, Feb 9 - Tue, Feb 17
SJO
San José
YWG
Winnipeg
$656 Roundtrip, found 8 hours ago
$656
Roundtrip
found 8 hours ago
Select United flight, departing Mon, Feb 9 from San José to Winnipeg, returning Tue, Feb 17, priced at $656 found 8 hours ago
United
Fri, Dec 12 - Mon, Jan 12
SJO
San José
YWG
Winnipeg
$662 Roundtrip, found 1 day ago
$662
Roundtrip
found 1 day ago
Select United flight, departing Fri, Dec 12 from San José to Winnipeg, returning Mon, Jan 12, priced at $662 found 1 day ago
avianca
Fri, Oct 24 - Tue, Oct 28
SJO
San José
YWG
Winnipeg
$682 Roundtrip, found 16 hours ago
$682
Roundtrip
found 16 hours ago
Select avianca flight, departing Fri, Oct 24 from San José to Winnipeg, returning Tue, Oct 28, priced at $682 found 16 hours ago
Air Canada
Wed, Jan 21 - Wed, Feb 4
SJO
San José
YWG
Winnipeg
$797 Roundtrip, found 2 days ago
$797
Roundtrip
found 2 days ago
Select Air Canada flight, departing Wed, Jan 21 from San José to Winnipeg, returning Wed, Feb 4, priced at $797 found 2 days ago
Delta
Fri, Feb 6 - Tue, Feb 24
SJO
San José
YWG
Winnipeg
$873 Roundtrip, found 2 days ago
$873
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Feb 6 from San José to Winnipeg, returning Tue, Feb 24, priced at $873 found 2 days ago
Aeromexico
Wed, Feb 4 - Tue, Feb 17
SJO
San José
YWG
Winnipeg
$891 Roundtrip, found 2 days ago
$891
Roundtrip
found 2 days ago
Select Aeromexico flight, departing Wed, Feb 4 from San José to Winnipeg, returning Tue, Feb 17, priced at $891 found 2 days ago

Find the cheapest month to fly from San José (SJO) to Winnipeg (YWG)

September is typically the cheapest month to fly

From $606 - $1,338 per traveler.

Frequently asked questions

How much does a flight from Juan Santamaria Intl. Airport (SJO) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) cost?
Secure a cheap one-way flight from $364 or cheap return flight from $630 from Juan Santamaria Intl. Airport (SJO) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Juan Santamaria Intl. Airport (SJO) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
December is the least expensive month to fly from SJO to YWG. Planning your trip for the off-season is often the key to scoring lower fares.
What is the cheapest airline that flies from Juan Santamaria Intl. Airport (SJO) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
To find the cheapest airline that'll fly you from SJO to YWG, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and ideal departure window. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from Juan Santamaria Intl. Airport (SJO) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
There aren't any daily nonstop flights available from Juan Santamaria Intl. Airport (SJO) to Winnipeg James Armstrong Richardson Intl. Airport (YWG). But you can choose flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be soaring above the clouds in no time at all.
What day of the week has the most flights from SJO to YWG?
Friday is usually the busiest day for flights, while Tuesday is often the quietest.* Keep in mind that flight schedules can vary depending on various factors, including the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Juan Santamaria Intl. Airport (SJO) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
To arrive at Winnipeg James Armstrong Richardson Intl. Airport (YWG) without delays, opt for a flight that leaves from Juan Santamaria Intl. Airport (SJO) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Juan Santamaria Intl. Airport (SJO) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) last-minute?
Last-minute fares from SJO to YWG are typically more expensive. To lock in the cheapest rates, start looking for flights as early as possible. That said, if you're flexible with your travel plans, you may land a cheap ticket right before your trip.
Is it cheaper to book a SJO to YWG flight and hotel package?
Opting for a SJO to YWG flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Pick from our impressive range of accommodations and then add car rentals, flights and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Juan Santamaria Intl. Airport (SJO) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
Usually, it's possible to reschedule or cancel your SJO to YWG flight. However, if it's been more than 24 hours since booking, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Origin airport
Juan Santamaría Intl.
Destination airport
Winnipeg James Armstrong Richardson Intl.
Airlines serving
Air Canada, Delta, United
Roundtrip price
$630
Distance
2856 mi

Book with confidence

San José to Winnipeg Flights

The cheapest times to fly from San José to Winnipeg

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from San José to Winnipeg are during the month of December. You can find some of the cheapest flights from San José to Winnipeg with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from San José to Winnipeg

Sunday is one of the best days to book for cheap flights from San José to Winnipeg: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from San José to Winnipeg

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from San José to Winnipeg in 2025. You can also book with separate airlines for your outbound and return journeys, from $364 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap San José to Winnipeg flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your San José to Winnipeg airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

San José to Winnipeg Flights

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*Available to One Key members.