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Cheap flights from Winnipeg to San José from C$ 388

YWG — SJO
19 Nov — 26 Nov1
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

Wed 9/123:15 p.m. -
2 stops29h 24m
Sun 24/16:40 a.m. -
2 stops39h 15m
Deal found 17/10C$ 846
Thu 3/129:40 a.m. -
2 stops34h 59m
Wed 9/122:25 p.m. -
2 stops46h 58m
Deal found 18/10C$ 853
Sat 24/104:10 p.m. -
1 stop31h 40m
Wed 28/108:20 a.m. -
1 stop31h 18m
Deal found 15/10C$ 863
Sat 24/103:05 p.m. -
1 stop32h 45m
Mon 26/108:20 a.m. -
1 stop24h 45m
Deal found 15/10C$ 865
Sat 24/104:10 p.m. -
1 stop31h 40m
Fri 30/105:35 a.m. -
2 stops27h 30m
Deal found 15/10C$ 866
Sun 8/113:15 p.m. -
2 stops22h 07m
Tue 17/118:45 a.m. -
2 stops28h 38m
Deal found 16/10C$ 870
Sat 24/103:05 p.m. -
1 stop32h 45m
Thu 29/107:45 a.m. -
2 stops33h 40m
Deal found 15/10C$ 872
Mon 16/113:15 p.m. -
2 stops22h 07m
Thu 19/112:25 p.m. -
2 stops22h 58m
Deal found 17/10C$ 873
Mon 16/113:15 p.m. -
2 stops23h 07m
Wed 25/112:25 p.m. -
2 stops21h 58m
Deal found 19/10C$ 874
Mon 26/106:15 a.m. -
2 stops41h 35m
Wed 28/108:20 a.m. -
1 stop24h 45m
Deal found 15/10C$ 876
Mon 26/106:15 a.m. -
1 stop17h 15m
Thu 29/107:45 a.m. -
2 stops33h 40m
Deal found 15/10C$ 877

Find flight deals from Winnipeg to San José

Round-trip from

C$ 800

One-way from

C$ 388

Popular in

December

Cheapest in

April

Average price

C$ 977
United Airlines
  • United Airlines
  • 6/1-26/1
  • 4 total stops
  • 54h 56m total
  • Winnipeg to San José
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Air Canada
  • Air Canada
  • 29/11-31/12
  • 1 total stop
  • 14h 45m total
  • Winnipeg to San José
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 137 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 76 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2026
Search Deals

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

Sun 29/11

9:05 a.m.-11:50 p.m.

1 stop14h 45m

San José Juan Santamaria Intl

Wed 31/12

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

Nonstop0h 00m

C$ 388

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Tue 5/1

9:40 a.m.-1:15 p.m.

2 stops27h 35m

San José Juan Santamaria Intl

Wed 31/12

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

Nonstop0h 00m

C$ 439

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sat 5/12

7:55 p.m.-10:30 p.m.

1 stop26h 35m

San José Juan Santamaria Intl

Wed 31/12

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

Nonstop0h 00m

C$ 453
Quickest round-trip

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Thu 3/12

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

1 stop14h 15m

San José Juan Santamaria Intl

Wed 31/12

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

Nonstop0h 00m

C$ 456

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Wed 6/1

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

1 stop28h 15m

San José Juan Santamaria Intl

Wed 27/1

2:25 p.m.-7:28 p.m.

2 stops29h 03m

C$ 800

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 8/3

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

2 stops29h 22m

San José Juan Santamaria Intl

Mon 22/3

7:45 a.m.-6:41 p.m.

2 stops33h 56m

C$ 821

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Fri 29/1

8:00 a.m.-7:25 a.m.

2 stops23h 25m

San José Juan Santamaria Intl

Fri 12/2

2:25 p.m.-6:41 p.m.

2 stops28h 16m

C$ 824

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 24/1

9:40 a.m.-12:15 p.m.

2 stops26h 35m

San José Juan Santamaria Intl

Sat 6/2

6:40 a.m.-9:55 p.m.

2 stops15h 15m

C$ 835

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 1/2

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

2 stops29h 22m

San José Juan Santamaria Intl

Sat 6/2

1:15 a.m.-9:55 p.m.

2 stops20h 40m

C$ 853

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Thu 11/2

9:40 a.m.-12:15 p.m.

2 stops26h 35m

San José Juan Santamaria Intl

Sun 21/2

6:40 a.m.-9:55 p.m.

2 stops39h 15m

C$ 862

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/10

Sorted by cheapest first

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

How much does it cost to fly round-trip from Winnipeg to San José?

Airfare is below average for this route at the moment.

Winnipeg to San José flights typically cost between C$ 907 and C$ 991 in January.
The cheapest round-trip price found within the last 5 days was C$ 783 on United Airlines (10 Jan-21 Jan).

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
11,784 reviews
Check prices

Boarding

7.3

Food

6.3

Entertainment

6.8

Overall

7.1

Crew

7.8

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
11,784 reviews
Air Canada
7.1
Good
11,784 reviews
Check prices

Boarding

7.3

Food

6.3

Entertainment

6.8

Overall

7.1

Crew

7.8

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 34h 16m. 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$ 837, 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$ 837AverageC$ 1,105FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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