Cheap flights from Winnipeg to San Jose, Costa Rica from C$395 YWG → SJO
Winnipeg James Armstrong Richardson International Airport (YWG) → Juan Santamaria International Airport (SJO)
The cheapest one-way found recently is C$395 (US$277) with WestJet, 29 Jan 2027, found 2 days ago.
- Cheapest one-way found recently
- C$395 (US$277), found 2 days ago
One-way
The cheapest one-way fare on each of 5 departure dates is usually C$415 (US$291) to C$422 (US$296).
Cheapest one-way found recently
C$395 (US$277)
29 Jan 2027 · WestJet
Winnipeg James Armstrong Richardson International Airport (YWG) → Juan Santamaria International Airport (SJO)
Leaves 10:35 p.m. · 25 h trip
3 stops
found 2 days ago
Cheapest nonstop one-way
None seen yet.
Found recently, and the cheapest we hold
C$395 (US$277) 29 Jan 2027found 2 days agoOpen this trip
It is also the cheapest one-way we hold, of any age.
What have prices looked like?
Over 5 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was C$395 (US$277) to C$470 (US$330).
At C$395 (US$277), the cheapest one-way found recently is at the low end of that range.
5 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good one-way price?
Compared with the cheapest one-way fare on each of 5 departure dates from 16 Jan 2027 to 29 Jan 2027, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
No. We hold one-way fares on 2 other departure dates within 3 days of 29 Jan 2027, and none is cheaper.
Every date we hold
5 fares on 5 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 16 Jan 2027 | C$438 (US$307) | Porter Airlines Canada | Winnipeg James Armstrong Richardson International Airport (YWG) → Juan Santamaria International Airport (SJO) | 1 stop | found 2 days ago | Open this trip |
| 23 Jan 2027 | C$415 (US$291) | WestJet | Winnipeg James Armstrong Richardson International Airport (YWG) → Juan Santamaria International Airport (SJO) | 3 stops | found 2 days ago | Open this trip |
| 27 Jan 2027 | C$416 (US$292) | WestJet | Winnipeg James Armstrong Richardson International Airport (YWG) → Juan Santamaria International Airport (SJO) | 3 stops | found 2 days ago | Open this trip |
| 28 Jan 2027 | C$422 (US$296) | Air Canada | Winnipeg James Armstrong Richardson International Airport (YWG) → Juan Santamaria International Airport (SJO) | 2 stops | found 2 days ago | Open this trip |
| 29 Jan 2027 | C$395 (US$277) | WestJet | Winnipeg James Armstrong Richardson International Airport (YWG) → Juan Santamaria International Airport (SJO) | 3 stops | found 2 days ago | Open this trip |
Airlines on the cheapest dates: WestJet, Porter Airlines Canada, Air Canada.
Premium cabin fares from Winnipeg to San Jose
We hold no premium economy, business or first-class fares for this route: we collect them for the busiest routes, and this one is not among them yet.
Today's prices for 29 Jan 2027 in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Winnipeg to San Jose?
One-way
Not enough history yet: we have 5 days of one-way prices, 24 Sept to 11 Nov, and compare booking times once 3 booking ranges have 7 days each.
Live price for these dates
The cheapest one-way found recently is for 29 Jan 2027. A live search on this page shows what those dates cost now, for one adult in economy.
Questions about this trip
How much is a one-way flight from Winnipeg to San Jose?
The cheapest one-way found recently is C$395 (US$277) with WestJet, 29 Jan 2027, found 2 days ago. The cheapest one-way fare on each of 5 departure dates is usually C$415 (US$291) to C$422 (US$296).
How long is the flight from Winnipeg to San Jose?
The cheapest one-way found recently, with WestJet on 29 Jan 2027, takes 25 h with 3 stops.
Which airlines have the cheapest flights from Winnipeg to San Jose?
Between 16 Jan 2027 and 29 Jan 2027, WestJet has the cheapest one-way on 3 of the 5 departure dates we hold, Porter Airlines Canada on 1 and Air Canada on 1.
Prices are what travelers' searches on Aviasales found in the last 7 days: the price the seller showed on Aviasales; bags may cost extra. Canadian dollars at the Bank of Canada rate of 2026-11-12, US dollars in brackets. Fares change, so check today's price before you book. How our prices work