YWG - SJO

C$ 371 Find Cheap Flights from Winnipeg to San José – Compare and Save

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Everything you should know

Cheapest round-trip
C$ 763
Typical prices: C$ 965-C$ 1,397
Air Canada
Thu 29/11Mon 3/12
YWG - SJO • 2 stops
Cheapest one-way flights
C$ 371
Typical prices: C$ 450-C$ 632
Porter Airlines
Tue 4/12
YWG - SJO • 1 stop
Direct flights
Not available
There are currently no direct flights between Winnipeg and San José. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
April
Cheapest • 35% price drop
December
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Chicago O'Hare Intl (ORD)
Cheapest • Avg C$ 838 (round-trip)
Toronto Pearson Intl (YYZ)
Shortest trip • 11h 43m (one-way)
Insights
Insights
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We hope you enjoy your trip to San José!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Winnipeg to San José (YWG-SJO)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Winnipeg to San José

Sun, 29 Nov - Thu, 3 Dec
Air Canada Logo
6:00 a.m. - 11:50 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
17h 50m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:45 a.m. - 6:25 p.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
33h 40m2 stops Toronto Pearson Intl Ottawa
C$ 763Air Canada
Sun, 29 Nov - Thu, 3 Dec
Air Canada Logo
8:05 a.m. - 11:50 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
15h 45m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:45 a.m. - 6:25 p.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
33h 40m2 stops Toronto Pearson Intl Ottawa
C$ 763Air Canada
Sun, 29 Nov - Thu, 3 Dec
Air Canada Logo
8:05 a.m. - 11:50 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
15h 45m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:45 a.m. - 7:09 p.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
10h 24m1 stop Toronto Pearson Intl
C$ 763Air Canada
Sun, 29 Nov - Thu, 3 Dec
Air Canada Logo
6:00 a.m. - 11:50 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
17h 50m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:45 a.m. - 6:25 p.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
33h 40m2 stops Toronto Pearson Intl Ottawa
C$ 764Air Canada
Sun, 29 Nov - Thu, 3 Dec
Air Canada Logo
8:05 a.m. - 11:50 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
15h 45m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:45 a.m. - 6:25 p.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
33h 40m2 stops Toronto Pearson Intl Ottawa
C$ 764Air Canada
Sun, 29 Nov - Thu, 3 Dec
Air Canada Logo
8:05 a.m. - 11:50 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
15h 45m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:45 a.m. - 7:09 p.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
10h 24m1 stop Toronto Pearson Intl
C$ 764Air Canada
Sun, 29 Nov - Thu, 3 Dec
Air Canada Logo
6:00 a.m. - 11:50 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
17h 50m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:45 a.m. - 6:25 p.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
33h 40m2 stops Toronto Pearson Intl Ottawa
C$ 777Air Canada
Tue, 1 Dec - Wed, 9 Dec
Multiple Airlines Logo
8:35 p.m. - 9:25 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
24h 50m2 stops Calgary Toronto Pearson Intl
Multiple Airlines Logo
11:55 p.m. - 7:50 p.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
19h 55m1 stop Toronto Pearson Intl
C$ 780Multiple Airlines
Sat, 7 Nov - Mon, 16 Nov
United Airlines Logo
2:15 p.m. - 11:25 a.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
21h 10m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
United Airlines Logo
12:35 p.m. - 12:23 p.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
23h 48m2 stops Houston George Bush Intcntl Chicago O'Hare Intl
C$ 792United Airlines
Sat, 7 Nov - Mon, 16 Nov
United Airlines Logo
2:15 p.m. - 1:22 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
23h 07m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
United Airlines Logo
8:45 a.m. - 12:23 p.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
27h 38m2 stops Houston George Bush Intcntl Chicago O'Hare Intl
C$ 795United Airlines
Booking Insights

Price, demand, and travel trends for Winnipeg to San José flights

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights from Winnipeg to San José with more confidence.

How much is a round-trip flight from Winnipeg to San José?

Round-trip flights from Winnipeg to San José start at C$ 763. Prices are below average for this route right now, with typical round-trip fares ranging from C$ 965 to C$ 1,397. The lowest price found in the past 5 days was C$ 763 on Air Canada.

What's the cheapest day of the week to fly from Winnipeg to San José?

Monday is the cheapest day of the week to fly from Winnipeg to San José and is 21% cheaper than the average day. Friday is the most expensive day with flight prices 6% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Winnipeg to San José?

•April is the cheapest month to fly from Winnipeg to San José at C$ 787 round-trip.
•December (C$ 1,639) and March (C$ 1,583) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 108% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Winnipeg to San José flights

Low season

May

Cheapest flight

C$ 371
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly (35% more expensive on average)
Flights from Winnipeg to San José

When to book flights from Winnipeg to San José

Are your dates flexible? Find out the best times to travel from Winnipeg to San José based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Winnipeg to San José flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines, and booking questions.

  • Which airports can I use when flying from Winnipeg to San José?

    Flights from Winnipeg to San José usually depart from Winnipeg (YWG) and arrive at San José Juan Santamaria Intl (SJO).

  • Which cabin classes can I book on flights from Winnipeg to San José?

    Two cabin classes are available on flights from Winnipeg to San José:

    • Economy Class
    • Business Class

  • Which airports do connecting flights from Winnipeg to San José pass through?

    One-stop flights from Winnipeg to San José most commonly connect through:

    • Toronto Pearson Intl (YYZ) – 95% of one-stop connections
    • Chicago O'Hare Intl (ORD) – 2% of one-stop connections
    • Montreal Pierre Elliott Trudeau Intl (YUL) – 2% of one-stop connections

    Toronto Pearson Intl (YYZ) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Winnipeg to San José?

    Yes. Being flexible with your travel dates can save you up to 26% on the Winnipeg to San José route. Monday is the cheapest departure day at C$ 969 round-trip on average, while Friday is the most expensive at C$ 1,294, a difference of C$ 325. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • Which popular places can I visit in San José?

    Some of the most popular sights in San José are Estadio Nacional de Costa Rica, Parque Nacional, and Parque Metropolitano La Sabana. These are among the most viewed places in San José on KAYAK.

  • How long does a flight from Winnipeg to San José take?

    A direct flight from Winnipeg to San José takes 0h 00m, covering 7,394 km.

  • Do I need a passport to fly from Winnipeg to San José?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • Have flight prices from Winnipeg to San José changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about C$ 763 to C$ 5,672. That means the highest observed fare was about 7x higher than the lowest one.

  • How are flight prices from Winnipeg to San José looking right now?

    One-way fares from Winnipeg to San José are currently lower than usual. Average one-way flight prices are about C$ 390, which is 31% below the typical average for this route.

  • How much time can I save by choosing a different layover airport when travelling from Winnipeg to San José?

    Flying via Toronto Pearson Intl (YYZ) gives the shortest average 1-stop total travel time at 11h 43m, compared with 13h 11m via Montreal Pierre Elliott Trudeau Intl (YUL) and 22h 13m via Chicago O'Hare Intl (ORD).

  • What is the time difference between Winnipeg and San José?

    San José is 1 hour behind Winnipeg (Central Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at San José Juan Santamaria Intl Airport (SJO)?

    San José Juan Santamaria Intl Airport (SJO) hosts 5 major car rental companies, with daily rates starting from around C$ 2 for economy cars. Top options include:
    • Budget
    • Avis
    • Priceless
    • Routes Car & Truck Rentals
    • Payless

  • How much should I expect to pay for a Winnipeg to San José flight?

    Round-trip flights from Winnipeg to San José range from C$ 965 to C$ 1,397, with an average of C$ 1,213 over the past 12 months. Anything below C$ 965 counts as a good deal.

Your guide to booking Winnipeg to San José flights

Get tips on when to book, when to fly, and what to know before your trip.
  • If your dates are flexible, aim for a Monday departure instead of Friday. On this route, Monday flights average C$ 969 – about C$ 325 less than Friday (25% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Winnipeg to San José trip for April. Fares historically average C$ 787 round-trip in that month – typically C$ 852 less than the most expensive month, which is December (based on the last 12 months).

More options for your flight from Winnipeg to San José

Complete your trip to San José with a hotel stay or car rental

Car rentals in San José
Hotels in San José
Vacations in San José