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Cheap flights from San José to Winnipeg from C$ 920

SJO — YWG
24 Nov — 1 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from San José to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from San José to Winnipeg

Sat 12/122:05 p.m. -
2 stops19h 10m
Wed 17/211:00 a.m. -
1 stop12h 55m
Deal found 23/10C$ 920
Sat 12/126:40 a.m. -
2 stops38h 15m
Wed 17/29:40 a.m. -
2 stops51h 35m
Deal found 23/10C$ 973
Tue 29/126:40 a.m. -
2 stops38h 17m
Sat 9/18:00 a.m. -
2 stops30h 22m
Deal found 23/10C$ 1,019
Fri 20/1112:35 p.m. -
2 stops23h 48m
Fri 4/129:40 a.m. -
2 stops45h 45m
Deal found 20/10C$ 1,025
Fri 20/1111:25 a.m. -
2 stops13h 19m
Fri 4/129:05 p.m. -
1 stop27h 45m
Deal found 20/10C$ 1,063
Fri 20/118:45 a.m. -
1 stop12h 29m
Fri 4/1212:05 p.m. -
1 stop11h 25m
Deal found 20/10C$ 1,183
Tue 29/121:16 p.m. -
1 stop29h 39m
Sat 9/111:40 a.m. -
2 stops36h 15m
Deal found 23/10C$ 1,321
Tue 3/111:16 p.m. -
1 stop29h 39m
Sat 7/1111:00 a.m. -
1 stop13h 50m
Deal found 24/10C$ 1,350

Find flight deals from San José to Winnipeg

Round-trip from

C$ 920

One-way from

C$ 485

Popular in

August

Cheapest in

April

Average price

C$ 1,505
12/12-17/2
  • 12/12-17/2
  • 3 total stops
  • 32h 05m total
  • San José to Winnipeg
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19/11-31/12
  • 19/11-31/12
  • 2 total stops
  • 12h 09m total
  • San José to Winnipeg
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Highest demand for flights based on searches. 13% potential increase in price (C$ 314 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease (C$ 110 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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Cheapflights Fare Finder

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

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Route

Depart

Return

Price

Cheapest round-trip

San JoséWinnipeg

SJO San José Juan Santamaria Intl - YWG Winnipeg

SJOYWG

San José Juan Santamaria Intl

Sat 12/12

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

2 stops38h 15m

Winnipeg

Wed 17/2

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

2 stops51h 35m

C$ 973

San JoséWinnipeg

SJO San José Juan Santamaria Intl - YWG Winnipeg

SJOYWG

San José Juan Santamaria Intl

Tue 29/12

6:40 a.m.-9:57 p.m.

2 stops38h 17m

Winnipeg

Sat 9/1

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

2 stops30h 22m

C$ 1,019

San JoséWinnipeg

SJO San José Juan Santamaria Intl - YWG Winnipeg

SJOYWG

San José Juan Santamaria Intl

Fri 20/11

12:35 p.m.-1:23 p.m.

2 stops23h 48m

Winnipeg

Fri 4/12

9:40 a.m.-6:25 a.m.

2 stops45h 45m

C$ 1,025

San JoséWinnipeg

SJO San José Juan Santamaria Intl - YWG Winnipeg

SJOYWG

San José Juan Santamaria Intl

Fri 20/11

11:25 a.m.-1:44 a.m.

2 stops13h 19m

Winnipeg

Fri 4/12

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

1 stop27h 45m

C$ 1,063

San JoséWinnipeg

SJO San José Juan Santamaria Intl - YWG Winnipeg

SJOYWG

San José Juan Santamaria Intl

Fri 20/11

8:45 a.m.-11:24 a.m.

1 stop25h 39m

Winnipeg

Fri 4/12

7:00 a.m.-10:30 p.m.

2 stops16h 30m

C$ 1,183

San JoséWinnipeg

SJO San José Juan Santamaria Intl - YWG Winnipeg

SJOYWG

San José Juan Santamaria Intl

Tue 29/12

1:16 p.m.-7:55 p.m.

1 stop29h 39m

Winnipeg

Sat 9/1

11:40 a.m.-10:55 p.m.

2 stops36h 15m

C$ 1,321
Quickest round-trip

San JoséWinnipeg

SJO San José Juan Santamaria Intl - YWG Winnipeg

SJOYWG

San José Juan Santamaria Intl

Sun 15/11

8:45 a.m.-10:14 p.m.

1 stop12h 29m

Winnipeg

Sun 22/11

12:20 p.m.-10:30 p.m.

1 stop11h 10m

C$ 2,092

San JoséWinnipeg

SJO San José Juan Santamaria Intl - YWG Winnipeg

SJOYWG

San José Juan Santamaria Intl

Thu 19/11

12:37 a.m.-10:52 p.m.

3 stops21h 15m

Winnipeg

Fri 4/12

7:00 a.m.-12:30 p.m.

3 stops30h 30m

C$ 5,295

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/10

Sorted by cheapest first

Best time to book a flight from San José to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from San José with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

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

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

Airfare is below average for this route at the moment.

San José to Winnipeg flights typically cost between C$ 1,129 and C$ 1,335 in December.
The cheapest round-trip price found within the last 5 days was C$ 920 on Multiple Airlines (12 Dec-17 Feb).

Related info for your journey

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

    Airlines like United Airlines and Air Canada fly from San José to Winnipeg in about 25h 39m. The time it takes to get you to your destination can typically vary by up to 12h 36m. Airlines will cover a distance of 4595 km. Both multi-stop and direct flights can be found to your destination and back.

  • Can I find deals for flights from San José to Winnipeg that include hotel bookings?

    Yes. In addition to deals on San José to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San José to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San José to Winnipeg.

  • Can I find deals for business class flights from San José to Winnipeg?

    Yes. Cheapflights offers flight deals from San José to Winnipeg 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

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How does Cheapflights help users find flights from San José to Winnipeg?

Cheapflights makes it easy to find San José to Winnipeg flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from San José to Winnipeg?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Winnipeg from San José.

Can Cheapflights find flights from San José to Winnipeg with no change fees?

Need flexible booking options for your flight to Winnipeg from San José? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

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