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Cheap flights from Winnipeg to San José from C$ 365

YWG — SJO
9 Oct — 16 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

Tue 27/1012:45 p.m. -
1 stop10h 45m
Sun 1/118:45 a.m. -
1 stop12h 29m
Deal found 7/9C$ 698
Sun 8/116:55 p.m. -
1 stop27h 35m
Tue 17/118:45 a.m. -
1 stop10h 24m
Deal found 8/9C$ 722
Sun 29/118:05 a.m. -
1 stop15h 45m
Thu 3/128:45 a.m. -
1 stop10h 24m
Deal found 5/9C$ 738
Fri 23/105:25 p.m. -
2 stops54h 25m
Sat 14/119:20 a.m. -
1 stop24h 40m
Deal found 6/9C$ 742
Sat 7/116:55 p.m. -
1 stop27h 35m
Mon 16/119:20 a.m. -
1 stop31h 18m
Deal found 8/9C$ 754

Find flight deals from Winnipeg to San José

Round-trip from

C$ 698

One-way from

C$ 365

Popular in

September

Cheapest in

April

Average price

C$ 2,058
Air Canada
  • Air Canada
  • 27/10-1/11
  • 2 total stops
  • 23h 14m total
  • Winnipeg to San José
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Air Canada
  • Air Canada
  • 5/12-31/12
  • 1 total stop
  • 27h 35m total
  • Winnipeg to San José
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (C$ 63 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease (C$ 115 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 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

6:55 p.m.-10:30 p.m.

1 stop27h 35m

San José Juan Santamaria Intl

Wed 31/12

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

Nonstop0h 00m

C$ 365
Quickest round-trip

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 1/3

11:05 a.m.-10:25 p.m.

1 stop11h 20m

San José Juan Santamaria Intl

Wed 31/12

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

Nonstop0h 00m

C$ 390

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Tue 10/11

8:40 a.m.-1:22 p.m.

2 stops28h 42m

San José Juan Santamaria Intl

Wed 31/12

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

Nonstop0h 00m

C$ 412

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Fri 23/10

2:00 p.m.-12:21 p.m.

2 stops23h 21m

San José Juan Santamaria Intl

Wed 31/12

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

Nonstop0h 00m

C$ 423

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Thu 12/11

8:40 a.m.-1:22 p.m.

2 stops28h 42m

San José Juan Santamaria Intl

Wed 31/12

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

Nonstop0h 00m

C$ 423

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Tue 5/1

7:00 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$ 429

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Tue 27/10

7:15 a.m.-10:50 p.m.

2 stops16h 35m

San José Juan Santamaria Intl

Sun 1/11

8:45 a.m.-10:05 a.m.

2 stops25h 20m

C$ 707

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sun 10/1

7:00 a.m.-8:39 p.m.

2 stops37h 39m

San José Juan Santamaria Intl

Fri 29/1

8:45 a.m.-10:33 p.m.

2 stops13h 48m

C$ 736

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Tue 19/1

7:00 a.m.-8:39 p.m.

2 stops13h 39m

San José Juan Santamaria Intl

Fri 29/1

8:45 a.m.-10:33 p.m.

3 stops37h 48m

C$ 736

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sat 16/1

7:00 a.m.-1:22 p.m.

2 stops30h 22m

San José Juan Santamaria Intl

Thu 28/1

8:45 a.m.-10:33 p.m.

2 stops13h 48m

C$ 772

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

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 86% 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$ 1,241.

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 05m.

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 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
11,604 reviews
Check prices

Boarding

7.3

Entertainment

6.8

Comfort

7.1

Crew

7.8

Overall

7.1

Food

6.3

Reviews

1 / 20
2.0
Mediocre

Sylvia,Aug 2026

YYZ - PHL

Our flight from Kelowna was 5 hours delayed. We missed our connection. We were able to get to a hotel by 3:00 a.m. but the breakfast cost us $40. The hotel was good. We were rescheduled for the flight the next night when it was canceled. There were no hotel vouchers available which didn't matter because there were no hotel rooms available. We decided to just drive which was not easy doing a one-way rental to the United States. Worst possible trip I've ever had
Air Canada
7.1
Good
11,604 reviews
Air Canada
7.1
Good
11,604 reviews
Check prices

Boarding

7.3

Entertainment

6.8

Comfort

7.1

Crew

7.8

Overall

7.1

Food

6.3

Reviews

1 / 20
2.0
Mediocre

Sylvia,Aug 2026

YYZ - PHL

Our flight from Kelowna was 5 hours delayed. We missed our connection. We were able to get to a hotel by 3:00 a.m. but the breakfast cost us $40. The hotel was good. We were rescheduled for the flight the next night when it was canceled. There were no hotel vouchers available which didn't matter because there were no hotel rooms available. We decided to just drive which was not easy doing a one-way rental to the United States. Worst possible trip I've ever had

Related info for your journey

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

    Airlines like Air Canada and United Airlines fly from Winnipeg to San José in about 16h 35m. The time it takes to get you to your destination can typically vary by up to 21h 04m. The distance between Winnipeg and San José is about 4595 km. Both multi-stop and direct flights can be found to your destination and back.

  • What is the cheapest airline to fly from Winnipeg to San José round-trip?

    Air Canada, at C$ 818, was found to be the cheapest airline from Winnipeg to San José.. Users have found that Air Canada is 33% 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$ 818AverageC$ 1,238FlexibilityNo 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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