YWG - SJO

C$ 365 Find Cheap Flights from Winnipeg to San José – Compare and Save

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Everything you should know

Cheapest round-trip
C$ 698
Typical prices: C$ 954-C$ 1,381
Air Canada
Sat 27/10Thu 1/11
YWG - SJO • 1 stop
Cheapest one-way flights
C$ 365
Typical prices: C$ 444-C$ 624
Air Canada
Wed 5/12
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$ 829 (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

Tue, 27 Oct - Sun, 1 Nov
Air Canada Logo
12:45 p.m. - 10:30 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
10h 45m1 stop Toronto Pearson Intl
Air Canada Logo
8:45 a.m. - 9:14 p.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
12h 29m1 stop Toronto Pearson Intl
C$ 698Air Canada
Tue, 27 Oct - Sun, 1 Nov
Air Canada Logo
7:15 a.m. - 10:30 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
16h 15m1 stop Toronto Pearson Intl
Air Canada Logo
8:45 a.m. - 10:05 a.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
25h 20m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
C$ 703Air Canada
Tue, 27 Oct - Sun, 1 Nov
Air Canada Logo
7:15 a.m. - 10:50 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
16h 35m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:45 a.m. - 10:05 a.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
25h 20m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
C$ 707Air Canada
Sun, 8 Nov - Tue, 17 Nov
Air Canada Logo
6:55 p.m. - 10:30 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
27h 35m1 stop Toronto Pearson 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$ 722Air Canada
Sun, 8 Nov - Tue, 17 Nov
Air Canada Logo
6:55 p.m. - 10:30 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
27h 35m1 stop Toronto Pearson Intl
Air Canada Logo
8:45 a.m. - 10:00 a.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
25h 15m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
C$ 727Air Canada
Mon, 1 Feb - Sun, 7 Feb
Air Canada Logo
6:00 a.m. - 10:30 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
40h 30m2 stops Ottawa Toronto Pearson Intl
Air Canada Logo
8:45 a.m. - 9:24 p.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
12h 39m1 stop Toronto Pearson Intl
C$ 728Air Canada
Mon, 1 Feb - Sun, 7 Feb
Air Canada Logo
3:05 p.m. - 10:30 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
31h 25m1 stop Toronto Pearson Intl
Air Canada Logo
8:45 a.m. - 12:24 a.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
15h 39m1 stop Toronto Pearson Intl
C$ 728Air Canada
Mon, 1 Feb - Sun, 7 Feb
Air Canada Logo
11:05 a.m. - 10:30 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
11h 25m1 stop Toronto Pearson 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$ 728Air Canada
Sun, 10 Jan - Fri, 29 Jan
United Airlines Logo
7:00 a.m. - 8:39 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
37h 39m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
United Airlines Logo
8:45 a.m. - 10:33 p.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
13h 48m2 stops Houston George Bush Intcntl Chicago O'Hare Intl
C$ 736United Airlines
Sun, 17 Jan - Tue, 26 Jan
United Airlines Logo
7:00 a.m. - 8:39 p.m.YWG  Winnipeg-SJO San José Juan Santamaria Intl
37h 39m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
United Airlines Logo
1:15 a.m. - 10:33 p.m.SJO  San José Juan Santamaria Intl-YWG Winnipeg
21h 18m2 stops Houston George Bush Intcntl Chicago O'Hare Intl
C$ 736United 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$ 698. Prices are below average for this route right now, with typical round-trip fares ranging from C$ 954 to C$ 1,381. The lowest price found in the past 5 days was C$ 698 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$ 778 round-trip.
  • December (C$ 1,620) and March (C$ 1,565) 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$ 365
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?

    Only Economy Class is available on flights from Winnipeg to San José.

  • 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$ 958 round-trip on average, while Friday is the most expensive at C$ 1,279, a difference of C$ 321. 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, Barrio Amón, and Parque Nacional. 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$ 698 to C$ 5,590. That means the highest observed fare was about 8x 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$ 395, which is 30% 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$ 1 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$ 954 to C$ 1,381, with an average of C$ 1,199 over the past 12 months. Anything below C$ 954 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$ 958 – about C$ 321 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$ 778 round-trip in that month – typically C$ 842 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