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Cheap flights from Winnipeg to San José from C$ 422

YWG — SJO
4 Dec — 11 Dec1
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 29/119:40 a.m. -
2 stops26h 45m
Thu 3/122:25 p.m. -
2 stops30h 30m
Deal found 2/11C$ 806
Tue 1/121:45 p.m. -
1 stop9h 45m
Fri 11/125:35 a.m. -
2 stops35h 03m
Deal found 3/11C$ 861
Sat 14/113:15 p.m. -
2 stops45h 10m
Wed 18/112:25 p.m. -
2 stops21h 58m
Deal found 4/11C$ 873
Sat 5/123:15 p.m. -
2 stops23h 07m
Sat 12/121:55 p.m. -
1 stop22h 28m
Deal found 2/11C$ 881
Sun 29/119:05 a.m. -
1 stop15h 45m
Thu 3/128:45 a.m. -
2 stops33h 40m
Deal found 30/10C$ 889
Tue 1/129:05 p.m. -
1 stop25h 20m
Fri 11/1211:55 p.m. -
1 stop11h 10m
Deal found 3/11C$ 919
Sun 1/119:40 a.m. -
2 stops26h 45m
Sun 8/116:40 a.m. -
2 stops38h 17m
Deal found 30/10C$ 937

Find flight deals from Winnipeg to San José

Round-trip from

C$ 799

One-way from

C$ 422

Popular in

December

Cheapest in

April

Average price

C$ 919
24/1-7/2
  • 24/1-7/2
  • 2 total stops
  • 24h 05m total
  • Winnipeg to San José
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United Airlines
  • United Airlines
  • 13/3-31/12
  • 2 total stops
  • 36h 39m total
  • Winnipeg to San José
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Highest demand for flights based on searches. 8% potential increase in price (C$ 135 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease (C$ 75 potential savings vs. average RT price).
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Average for round-trip flights in November 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

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sat 5/12

8:15 a.m.-10:30 p.m.

1 stop15h 15m

San José Juan Santamaria Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 429

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Fri 4/12

3:15 p.m.-1:22 p.m.

2 stops47h 07m

San José Juan Santamaria Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 431

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Thu 3/12

3:15 p.m.-10:00 p.m.

2 stops31h 45m

San José Juan Santamaria Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 432

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Thu 3/12

12:05 p.m.-10:30 p.m.

1 stop11h 25m

San José Juan Santamaria Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 449

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Tue 5/1

8:00 a.m.-1:22 p.m.

2 stops30h 22m

San José Juan Santamaria Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 460

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 14/3

8:40 a.m.-7:39 p.m.

2 stops35h 59m

San José Juan Santamaria Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 498
Quickest round-trip

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Tue 5/1

1:45 p.m.-10:30 p.m.

1 stop9h 45m

San José Juan Santamaria Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 557

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 25/1

9:40 a.m.-6:16 p.m.

2 stops33h 36m

San José Juan Santamaria Intl

Fri 5/2

1:25 p.m.-7:28 p.m.

1 stop29h 03m

C$ 803

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sat 23/1

9:40 a.m.-8:39 p.m.

2 stops11h 59m

San José Juan Santamaria Intl

Fri 12/2

2:25 p.m.-7:26 p.m.

2 stops28h 01m

C$ 804

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 24/1

8:00 a.m.-12:15 p.m.

1 stop29h 15m

San José Juan Santamaria Intl

Sun 7/2

6:40 a.m.-7:28 p.m.

2 stops35h 48m

C$ 804

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 14 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 78% 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$ 1,100.

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 37m.

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 4h 21m.

Reviews of airlines servicing San José

See what other customers who have flown with 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.
Air Canada
7.1
Good
11,854 reviews
Check prices

Boarding

7.3

Crew

7.8

Entertainment

6.8

Food

6.3

Overall

7.1

Comfort

7.1

Reviews

1 / 20
2.0
Mediocre

Hazel,Sep 2026

YYC - FRA

Air Canada cancelled our flight and rebooked us on Lufthansa, where we had to pay for checked luggage. We originally chose Air Canada because our Aeroplan credit card includes a free checked bag. It’s frustrating to face an extra charge because of a change we didn’t choose.
Air Canada
7.1
Good
11,854 reviews
Air Canada
7.1
Good
11,854 reviews
Check prices

Boarding

7.3

Crew

7.8

Entertainment

6.8

Food

6.3

Overall

7.1

Comfort

7.1

Reviews

1 / 20
2.0
Mediocre

Hazel,Sep 2026

YYC - FRA

Air Canada cancelled our flight and rebooked us on Lufthansa, where we had to pay for checked luggage. We originally chose Air Canada because our Aeroplan credit card includes a free checked bag. It’s frustrating to face an extra charge because of a change we didn’t choose.

Related info for your journey

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

    Airlines like United Airlines fly from Winnipeg to San José in about 33h 36m. 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 is the cheapest airline to fly from Winnipeg to San José round-trip?

    Air Canada, at C$ 830, was found to be the cheapest airline from Winnipeg to San José.. Users have found that Air Canada is 25% 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
Jacó
Heredia
Dominical
Alajuela
Monteverde

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Winnipeg to San José

Winnipeg to Liberia flights

Top airline flying from Winnipeg to San José

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 830AverageC$ 1,096FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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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