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481 € Cheap Flights from Winnipeg to San Jose Juan Santamaria

Compare Winnipeg to San Jose Juan Santamaria flight deals

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Flight deals from Winnipeg Airport to San Jose Juan Santamaria Airport

Looking for a cheap last-minute deal or the best return flight from Winnipeg Airport to San Jose Juan Santamaria Airport? If you want to travel next month, return fares start from 540 €. Find the lowest prices on one-way and return tickets right here.
San Jose.481 € per passenger.Departing Mon, 15 Jun, returning Fri, 26 Jun.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Winnipeg on Mon, 15 Jun, arriving in San Jose Juan Santamaria.Inbound indirect flight with Air Canada, departs from San Jose Juan Santamaria on Fri, 26 Jun, arriving in Winnipeg.Price includes taxes and charges.From 481 €, select.
San Jose.515 € per passenger.Departing Sun, 13 Dec, returning Sun, 20 Dec.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Winnipeg on Sun, 13 Dec, arriving in San Jose Juan Santamaria.Inbound indirect flight with Air Canada, departs from San Jose Juan Santamaria on Sun, 20 Dec, arriving in Winnipeg.Price includes taxes and charges.From 515 €, select.
San Jose.516 € per passenger.Departing Wed, 18 Nov, returning Wed, 16 Dec.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Winnipeg on Wed, 18 Nov, arriving in San Jose Juan Santamaria.Inbound indirect flight with Air Canada, departs from San Jose Juan Santamaria on Wed, 16 Dec, arriving in Winnipeg.Price includes taxes and charges.From 516 €, select.
San Jose.526 € per passenger.Departing Sat, 2 May, returning Mon, 11 May.Return flight with WestJet and Spirit Airlines.Outbound indirect flight with WestJet, departs from Winnipeg on Sat, 2 May, arriving in San Jose Juan Santamaria.Inbound indirect flight with Spirit Airlines, departs from San Jose Juan Santamaria on Mon, 11 May, arriving in Winnipeg.Price includes taxes and charges.From 526 €, select.
San Jose.528 € per passenger.Departing Wed, 29 Apr, returning Mon, 11 May.Return flight with Flair Airlines and Spirit Airlines.Outbound indirect flight with Flair Airlines, departs from Winnipeg on Wed, 29 Apr, arriving in San Jose Juan Santamaria.Inbound indirect flight with Spirit Airlines, departs from San Jose Juan Santamaria on Mon, 11 May, arriving in Winnipeg.Price includes taxes and charges.From 528 €, select.
San Jose.540 € per passenger.Departing Thu, 16 Apr, returning Thu, 23 Apr.Return flight with WestJet and Avianca.Outbound indirect flight with WestJet, departs from Winnipeg on Thu, 16 Apr, arriving in San Jose Juan Santamaria.Inbound indirect flight with Avianca, departs from San Jose Juan Santamaria on Thu, 23 Apr, arriving in Winnipeg.Price includes taxes and charges.From 540 €, select.
San Jose.542 € per passenger.Departing Thu, 17 Sep, returning Wed, 23 Sep.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Winnipeg on Thu, 17 Sep, arriving in San Jose Juan Santamaria.Inbound indirect flight with Air Canada, departs from San Jose Juan Santamaria on Wed, 23 Sep, arriving in Winnipeg.Price includes taxes and charges.From 542 €, select.
San Jose.756 € per passenger.Departing Wed, 29 Jul, returning Thu, 13 Aug.Return flight with WestJet and Frontier Airlines.Outbound indirect flight with WestJet, departs from Winnipeg on Wed, 29 Jul, arriving in San Jose Juan Santamaria.Inbound indirect flight with Frontier Airlines, departs from San Jose Juan Santamaria on Thu, 13 Aug, arriving in Winnipeg.Price includes taxes and charges.From 756 €, select.
San Jose.862 € per passenger.Departing Fri, 27 Mar, returning Sat, 4 Apr.Return flight with WestJet and Avianca.Outbound indirect flight with WestJet, departs from Winnipeg on Fri, 27 Mar, arriving in San Jose Juan Santamaria.Inbound indirect flight with Avianca, departs from San Jose Juan Santamaria on Sat, 4 Apr, arriving in Winnipeg.Price includes taxes and charges.From 862 €, select.
San Jose.929 € per passenger.Departing Sat, 21 Mar, returning Fri, 27 Mar.Return flight with WestJet and Spirit Airlines.Outbound indirect flight with WestJet, departs from Winnipeg on Sat, 21 Mar, arriving in San Jose Juan Santamaria.Inbound indirect flight with Spirit Airlines, departs from San Jose Juan Santamaria on Fri, 27 Mar, arriving in Winnipeg.Price includes taxes and charges.From 929 €, select.

Find the cheapest month to fly from Winnipeg to San Jose Juan Santamaria

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Winnipeg to San Jose Juan Santamaria flights are currently cheapest in June.
Mar
from 929 €
Apr
from 540 €
May
from 526 €
Jun
from 481 €
Jul
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Aug
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Sep
from 542 €
Oct
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Nov
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Dec
from 515 €
Jan
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Feb
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Winnipeg to San Jose Juan Santamaria: Alternative routes

Compare routes from Winnipeg to San Jose below. You may find an airport to fly into that's cheaper, faster, or easier than San Jose Juan Santamaria.

San Jose Juan Santamaria

15km from central San Jose
ClosestCheapest
from 481 €
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Quepos

54km from central San Jose
from 858 €
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Fortuna

68km from central San Jose
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Winnipeg to San Jose: Flight information

The things to know before you go.
Cheapest flight found481 €
Cheapest month to flyJune

Finding cheap flights from Winnipeg to San Jose Juan Santamaria: Frequently asked questions

The best price we found for a return flight from Winnipeg to San Jose Juan Santamaria is 481 €. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Winnipeg to San Jose Juan Santamaria. But we found flights with one or more stops from 481 €.
As of March 2026, there are no flights flying from Winnipeg to San Jose Juan Santamaria.
The cheapest month to fly from Winnipeg to San Jose Juan Santamaria is usually June.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Winnipeg Airport to San Jose Juan Santamaria Airport on Monday, 15 June 2026.
No airlines currently offer direct flights between Winnipeg Airport and San Jose Juan Santamaria Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to San Jose Juan Santamaria but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to San Jose is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Air Canada offers the cheapest flight tickets to San Jose Juan Santamaria.

Travelling from Winnipeg James Armstrong Richardson International Airport (YWG) to Juan Santamaria International Airport (SJO): what you need to know

  • San Jose's timezone is UTC-6, making San Jose one hour behind Winnipeg.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are tried-and-true travel tips. Be at the airport with enough time to catch your YWG to SJO flight.

  • You'll likely experience longer queues during popular months such as July. Arriving up to four hours in advance for an international flight and two hours for a domestic departure is a smart move.

How to find the cheapest flights from Winnipeg James Armstrong Richardson International Airport (YWG) to Juan Santamaria International Airport (SJO)

  • Currently, 243 € is the cheapest price we've seen for a one-way Winnipeg James Armstrong Richardson International Airport to Juan Santamaria International Airport flight. The best price for a return ticket is 481 €. Keep in mind that fares can change due to demand when booking.

  • Don't leave everything to the last moment. You're more likely to find cheap tickets from YWG to SJO if you book early. Airlines often offer some amazing early bird rates.

  • If you're willing to be flexible with your trip dates, use the 'Whole month' search tool. It'll give you the lowest price across the month when searching for a flight from Winnipeg James Armstrong Richardson International Airport to Juan Santamaria International Airport.

  • Landing cheap flights from YWG to SJO is a cinch with Price Alerts. All you need to do is create one of these automatic alerts and we'll get in touch when there's a better deal.

  • Tailor your trip with filters. Pick your ideal arrival and departure times, airlines and total journey duration. You can also sort the results by 'Cheapest,' 'Fastest' or 'Best' flights from Winnipeg James Armstrong Richardson International Airport to Juan Santamaria International Airport.

Handy information about Winnipeg James Armstrong Richardson International Airport (YWG)

  • The address for YWG is 2000 Wellington Avenue.

  • 61.28% of flights that leave from Winnipeg James Armstrong Richardson International Airport arrive at their destination on schedule.

  • Central Winnipeg to Winnipeg James Armstrong Richardson International Airport is around 8 kilometres. Depending on traffic, it'll take you about 15 minutes to get there if you're driving, catching a cab or ride-sharing.

  • You can expect a trip time of roughly 55 minutes when using public transport.

  • Get your holiday off to a relaxed start by staying near YWG. Whether you're boarding an early flight from Winnipeg James Armstrong Richardson International Airport to Juan Santamaria International Airport or want to avoid feeling rushed, these stays are ideal:

Arriving at Juan Santamaria International Airport (SJO)

  • If you have a late Winnipeg James Armstrong Richardson International Airport to Juan Santamaria International Airport flight, nothing beats the convenience of staying near the terminal. Grab your suitcases from the carousel and then be showered and snoozing shortly after at one of these hotels near SJO:

  • Pick up a Juan Santamaria International Airport rental car and discover San Jose and beyond with your own set of wheels. NextCar, Europcar and Dollar are popular providers to choose from here.

  • Lock in the lowest price by booking your vehicle from Juan Santamaria International Airport about three weeks before your trip.

Getting from Juan Santamaria International Airport (SJO) to central San Jose

  • Juan Santamaria International Airport to the centre of San Jose has a drive time of around 20 minutes. It's approximately 18 kilometres away.

  • Travelling to the centre on public transport takes about 2 hours 20 minutes.

When to fly to Juan Santamaria International Airport (SJO)

  • It's time to pick your travel dates for your flight from Winnipeg James Armstrong Richardson International Airport to Juan Santamaria International Airport. July is the busiest month to visit San Jose. If you like a more low-key vibe, go in May.

  • Book your flight from Winnipeg James Armstrong Richardson International Airport to Juan Santamaria International Airport for March if you'd like to visit San Jose during its warmest month. You can expect temperatures of between 12ºC (54ºF) and 29ºC (84ºF).

  • January sees average temperatures of between 12ºC (54ºF) and 26ºC (79ºF). Look for cheap tickets from YWG to SJO sometime around then if you'd rather travel in cooler conditions.

Explore more of Costa Rica

  • Limon is just one of the many cities in Costa Rica waiting to be discovered once you've seen the sights of San Jose. Around 113 kilometres away to the east, well-known attractions include Veragua Rainforest Park, Playa Bonita and Cruise Pier Puerto Limon.

  • Alajuela is another sought-after destination in Costa Rica and is around 18 kilometres north-west of San Jose. No journey is complete without experiencing La Perla Park, Los Duendes Park and Finca El Soto.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.