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Cheap flights from Winnipeg to San José from C$ 375

YWG — SJO
25 Sep — 2 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to San José

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to San José

Sun 8/117:15 a.m. -
2 stops16h 25m
Tue 17/115:00 a.m. -
2 stops16h 14m
Deal found 25/8C$ 737
Sun 15/118:40 a.m. -
2 stops35h 59m
Wed 25/118:45 a.m. -
2 stops36h 12m
Deal found 24/8C$ 742
Tue 17/1112:45 p.m. -
1 stop9h 45m
Mon 23/119:20 a.m. -
1 stop31h 18m
Deal found 24/8C$ 748
Sat 7/116:55 p.m. -
1 stop27h 35m
Mon 16/119:20 a.m. -
1 stop31h 18m
Deal found 25/8C$ 749
Fri 13/1112:40 a.m. -
1 stop10h 05m
Tue 24/1111:25 a.m. -
2 stops13h 19m
Deal found 24/8C$ 766
Fri 13/1112:40 a.m. -
1 stop10h 05m
Mon 23/1111:25 a.m. -
2 stops13h 19m
Deal found 24/8C$ 770
Thu 15/108:15 a.m. -
2 stops16h 25m
Thu 22/105:05 a.m. -
2 stops17h 42m
Deal found 25/8C$ 773
Sat 14/112:15 p.m. -
2 stops30h 24m
Wed 25/118:45 a.m. -
2 stops27h 38m
Deal found 24/8C$ 778

Find flight deals from Winnipeg to San José

Round-trip from

C$ 648

One-way from

C$ 375

Popular in

September

Cheapest in

April

Average price

C$ 839
Air Canada
  • Air Canada
  • 1/2-7/2
  • 2 total stops
  • 30h 54m total
  • Winnipeg to San José
Search Deals
Air Canada
  • Air Canada
  • 24/10
  • 1 total stop
  • 31h 40m total
  • Winnipeg to San José
Search Deals
Highest demand for flights based on searches. 1% potential increase in price (C$ 17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 111 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Winnipeg to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 8/11

8:05 a.m.-11:50 p.m.

1 stop15h 45m

San José Juan Santamaria Intl

Tue 17/11

8:45 a.m.-11:44 p.m.

1 stop14h 59m

C$ 749

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sat 7/11

6:55 p.m.-11:50 p.m.

2 stops28h 55m

San José Juan Santamaria Intl

Mon 16/11

9:20 a.m.-10:00 a.m.

1 stop24h 40m

C$ 753

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sat 14/11

2:15 p.m.-8:39 p.m.

2 stops30h 24m

San José Juan Santamaria Intl

Wed 25/11

8:45 a.m.-12:23 p.m.

2 stops27h 38m

C$ 778

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 29/11

8:40 a.m.-11:25 a.m.

2 stops26h 45m

San José Juan Santamaria Intl

Thu 3/12

2:25 p.m.-8:48 p.m.

2 stops30h 23m

C$ 788

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Tue 17/11

2:15 p.m.-1:22 p.m.

2 stops23h 07m

San José Juan Santamaria Intl

Wed 25/11

8:45 a.m.-12:23 p.m.

2 stops27h 38m

C$ 792

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 15/11

2:15 p.m.-11:25 a.m.

2 stops21h 10m

San José Juan Santamaria Intl

Tue 24/11

8:45 a.m.-12:23 p.m.

2 stops27h 38m

C$ 792

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 29/11

8:05 a.m.-11:50 p.m.

1 stop15h 45m

San José Juan Santamaria Intl

Thu 3/12

8:45 a.m.-6:25 p.m.

2 stops33h 40m

C$ 798

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 1/2

2:15 p.m.-8:39 p.m.

2 stops30h 24m

San José Juan Santamaria Intl

Sun 7/2

1:25 p.m.-11:39 a.m.

1 stop22h 14m

C$ 803

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sat 21/11

2:15 p.m.-11:25 a.m.

2 stops45h 10m

San José Juan Santamaria Intl

Sat 5/12

8:45 a.m.-11:39 a.m.

2 stops26h 54m

C$ 816

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sat 13/2

2:15 p.m.-8:39 p.m.

2 stops30h 24m

San José Juan Santamaria Intl

Mon 22/2

12:35 p.m.-11:39 a.m.

2 stops23h 04m

C$ 816

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/8

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to San José

What’s the top layover airport for flights from Winnipeg to San José?

Toronto (YYZ) – chosen by Cheapflights users on 92% of one-stop itineraries from Winnipeg to San José on Cheapflights.

What’s the cheapest layover airport for flights from Winnipeg to San José?

Toronto (YYZ) is the most affordable 1-stop option, with an average round-trip price of C$ 1,296.

What’s the fastest layover option from Winnipeg to San José?

Flights via Toronto (YYZ) have the shortest average one-way travel time for 1-stop routes: 11h 13m.

Which airport typically offers the quickest layover for flights from Winnipeg to San José?

Flights via Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 3h 46m.

Reviews of airlines servicing San José

See what other customers who have flown with United Airlines and Air Canada 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
10,122 reviews
Check prices

Overall

7.4

Entertainment

7.1

Crew

8.1

Boarding

7.7

Food

6.7

Comfort

7.3

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
10,122 reviews
United Airlines
7.4
Good
10,122 reviews
Check prices

Overall

7.4

Entertainment

7.1

Crew

8.1

Boarding

7.7

Food

6.7

Comfort

7.3

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
Air Canada
7.1
Good
11,532 reviews
United Airlines
7.4
Good
10,122 reviews
Check prices

Overall

7.4

Entertainment

7.1

Crew

8.1

Boarding

7.7

Food

6.7

Comfort

7.3

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

Related info for your journey

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

    Airlines like Air Canada fly from Winnipeg to San José in about 15h 15m. The time it takes to get you to your destination can typically vary by up to . The distance between Winnipeg and San José is about 4595 km.

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

    United Airlines, at C$ 673, was found to be the cheapest airline from Winnipeg to San José. An alternate airline flying to your destination would be Air Canada. Users have found that United Airlines is 47% cheaper than the other options available to this destination.

  • 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.

See more FAQs

Travelling to a place near San José?

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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Winnipeg to San José

Winnipeg to Liberia flights

Top 2 airlines flying from Winnipeg to San José

AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 673AverageC$ 794FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 821AverageC$ 1,285FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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Cheapflights simply makes it quick and affordable to book flights from Winnipeg to San José by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

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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Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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