Cheap flights from Winnipeg to San José from C$ 369
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 28/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJO
14 Jan — 21 Jan1
Round-trip
1 adult
Economy
Round-trip
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Winnipeg to San José Juan Santamaria Intl are usually found in July or September, booked 61 days in advance, depart on a Tuesday or Friday and return on a Monday
Cheap flight deals from Winnipeg to San José
Enter your travel dates to find the best prices.
Cheapest flights from Winnipeg to San José
Explore the most affordable flight options available from Winnipeg to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 15 December 2025.
Thu 18/122:20 p.m.YWG - SJO
2 stops22h 55mUnited Airlines
Thu 25/126:30 a.m.SJO - YWG
2 stops14h 21mUnited Airlines
Deal found 13/12C$ 1,086
Thu 18/128:40 a.m.YWG - SJO
2 stops11h 59mUnited Airlines
Thu 18/1211:28 p.m.SJO - YWG
2 stops36h 29mUnited Airlines
Deal found 13/12C$ 3,152
Thu 18/126:00 a.m.YWG - SJO
2 stops14h 14mAmerican Airlines
Thu 25/126:20 a.m.SJO - YWG
3 stops17h 15mAmerican Airlines
Deal found 13/12C$ 5,157
Best flights from Winnipeg to San José
Discover carefully curated flight deals from Winnipeg to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 15 December 2025.
Mon 12/18:00 a.m.YWG - SJO
1 stop28h 22mMultiple Airlines
Mon 19/11:30 p.m.SJO - YWG
2 stops35h 12mMultiple Airlines
Deal found 14/12C$ 657
Tue 3/32:20 p.m.YWG - SJO
2 stops27h 56mUnited Airlines
Tue 10/311:35 a.m.SJO - YWG
2 stops23h 22mUnited Airlines
Deal found 14/12C$ 671
Wed 25/28:05 p.m.YWG - SJO
1 stop27h 30mMultiple Airlines
Tue 3/34:15 p.m.SJO - YWG
2 stops19h 17mMultiple Airlines
Deal found 14/12C$ 720
Mon 12/12:20 p.m.YWG - SJO
2 stops22h 55mUnited Airlines
Wed 11/28:45 a.m.SJO - YWG
2 stops27h 12mUnited Airlines
Deal found 14/12C$ 763
Wed 14/17:30 a.m.YWG - SJO
3 stops28h 07mMultiple Airlines
Wed 21/112:33 p.m.SJO - YWG
2 stops23h 02mMultiple Airlines
Deal found 15/12C$ 755
Wed 14/12:20 p.m.YWG - SJO
2 stops22h 55mUnited Airlines
Wed 21/12:20 p.m.SJO - YWG
2 stops21h 37mUnited Airlines
Deal found 15/12C$ 821
Wed 21/17:30 a.m.YWG - SJO
3 stops28h 07mMultiple Airlines
Wed 4/212:33 p.m.SJO - YWG
3 stops47h 34mMultiple Airlines
Deal found 14/12C$ 760
Thu 26/32:20 p.m.YWG - SJO
2 stops32h 12mUnited Airlines
Mon 6/41:25 p.m.SJO - YWG
2 stops30h 27mUnited Airlines
Deal found 14/12C$ 828
Last-minute flights from Winnipeg to San José
Discover last-minute flight deals from Winnipeg to San José. Data last updated 15 December 2025 and is based on user searches.
Sun 11/12:20 p.m.YWG - SJO
1 stop22h 36mUnited Airlines
Sun 18/17:30 a.m.SJO - YWG
2 stops28h 27mUnited Airlines
Deal found 14/12C$ 845
Mon 12/18:00 a.m.YWG - SJO
1 stop28h 22mMultiple Airlines
Mon 19/11:30 p.m.SJO - YWG
2 stops35h 12mMultiple Airlines
Deal found 14/12C$ 657
Mon 12/12:20 p.m.YWG - SJO
2 stops22h 55mUnited Airlines
Wed 11/28:45 a.m.SJO - YWG
2 stops27h 12mUnited Airlines
Deal found 14/12C$ 763
Mon 12/12:20 p.m.YWG - SJO
2 stops22h 55mUnited Airlines
Mon 19/12:05 p.m.SJO - YWG
1 stop21h 52mUnited Airlines
Deal found 13/12C$ 983
Wed 14/17:30 a.m.YWG - SJO
3 stops28h 07mMultiple Airlines
Wed 21/112:33 p.m.SJO - YWG
2 stops23h 02mMultiple Airlines
Deal found 15/12C$ 755
Wed 14/12:20 p.m.YWG - SJO
2 stops22h 55mUnited Airlines
Wed 21/12:20 p.m.SJO - YWG
2 stops21h 37mUnited Airlines
Deal found 15/12C$ 821
Mon 19/12:20 p.m.YWG - SJO
2 stops30h 19mUnited Airlines
Fri 23/16:30 a.m.SJO - YWG
2 stops29h 27mUnited Airlines
Deal found 14/12C$ 874
Wed 21/17:30 a.m.YWG - SJO
3 stops28h 07mMultiple Airlines
Wed 4/212:33 p.m.SJO - YWG
2 stops30h 36mMultiple Airlines
Deal found 14/12C$ 749
Wed 21/12:20 p.m.YWG - SJO
1 stop22h 36mUnited Airlines
Wed 4/22:20 p.m.SJO - YWG
2 stops21h 37mUnited Airlines
Deal found 14/12C$ 967
One-way flights from Winnipeg to San José
Search for one-way flight options from Winnipeg to San José. Find affordable one-way fares based on user searches. Data last updated 15 December 2025.
Wed 28/12:40 p.m.YWG - SJO
3 stops24h 50mMultiple Airlines
Deal found 13/12C$ 369
Thu 22/12:20 p.m.YWG - SJO
1 stop22h 36mUnited Airlines
Deal found 14/12C$ 464
Thu 22/17:05 p.m.YWG - SJO
3 stops40h 40mAvianca
Deal found 14/12C$ 647
Wed 28/17:05 a.m.YWG - SJO
1 stop17h 00mAir Canada
Deal found 13/12C$ 742
Find flight deals from Winnipeg to San José
Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to San José (SJO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 15 December 2025.
Customize your flight search to find flights from Winnipeg to San José that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 15 December 2025.
Use the filters below to find and compare flights from Winnipeg to San José that are best for you.
Fly from
Winnipeg
Fly to
San José
Route
Depart
Return
Price
WinnipegSan José
YWG - SJO
YWGSJO
Winnipeg
Mon 12/1
8:00 a.m.-12:22 p.m.
1 stop28h 22m
San José Juan Santamaria Intl
Mon 19/1
1:30 p.m.-12:42 a.m.
2 stops35h 12m
C$ 657
WinnipegSan José
YWG - SJO
YWGSJO
Winnipeg
Tue 3/3
2:20 p.m.-6:16 p.m.
2 stops27h 56m
San José Juan Santamaria Intl
Tue 10/3
11:35 a.m.-11:57 a.m.
2 stops23h 22m
C$ 671
WinnipegSan José
YWG - SJO
YWGSJO
Winnipeg
Wed 25/2
8:05 p.m.-11:35 p.m.
1 stop27h 30m
San José Juan Santamaria Intl
Tue 3/3
4:15 p.m.-11:32 a.m.
2 stops19h 17m
C$ 720
WinnipegSan José
YWG - SJO
YWGSJO
Winnipeg
Wed 14/1
7:30 a.m.-11:37 a.m.
3 stops28h 07m
San José Juan Santamaria Intl
Wed 21/1
12:33 p.m.-11:35 a.m.
2 stops23h 02m
C$ 755
WinnipegSan José
YWG - SJO
YWGSJO
Winnipeg
Wed 21/1
7:30 a.m.-11:37 a.m.
3 stops28h 07m
San José Juan Santamaria Intl
Wed 4/2
12:33 p.m.-12:07 p.m.
3 stops47h 34m
C$ 760
WinnipegSan José
YWG - SJO
YWGSJO
Winnipeg
Mon 12/1
2:20 p.m.-1:15 p.m.
2 stops22h 55m
San José Juan Santamaria Intl
Wed 11/2
8:45 a.m.-11:57 a.m.
2 stops27h 12m
C$ 763
WinnipegSan José
YWG - SJO
YWGSJO
Winnipeg
Wed 14/1
2:20 p.m.-1:15 p.m.
2 stops22h 55m
San José Juan Santamaria Intl
Wed 21/1
2:20 p.m.-11:57 a.m.
2 stops21h 37m
C$ 821
WinnipegSan José
YWG - SJO
YWGSJO
Winnipeg
Thu 26/3
2:20 p.m.-9:32 p.m.
2 stops32h 12m
San José Juan Santamaria Intl
Mon 6/4
1:25 p.m.-8:52 p.m.
2 stops30h 27m
C$ 828
WinnipegSan José
YWG - SJO
YWGSJO
Winnipeg
Wed 28/1
2:40 p.m.-3:30 p.m.
3 stops24h 50m
C$ 369
WinnipegSan José
YWG - SJO
YWGSJO
Winnipeg
Thu 22/1
2:20 p.m.-12:56 p.m.
1 stop22h 36m
C$ 464
Flights are sorted by cheapest round-trip flights first.
Deals found on 13/12
Showing 1-10 of 12 results
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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
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Winnipeg to San José
Prices
More
How far ahead should I book a flight from Winnipeg to San José?
Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to San José. Price data was last updated on 12 December 2025.
To ensure you get the cheapest price possible for a flight from Winnipeg to San José, you should look to book at least 61 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Winnipeg to San José?
Currently, April is the cheapest month in which you can book a flight from Winnipeg to San José (average of C$ 651). Flying from Winnipeg to San José in June is currently the most expensive (average of C$ 953). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from YWG to SJO?
Find hourly flight availability from Winnipeg to San José. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 15 December 2025.
A simple way to save on the total cost of your ticket is to fly from Winnipeg to San José at noon. If you’re flexible enough to do this you can expect to save up to 42% on your trip compared to booking a flight in the morning.
How much does it cost to fly round-trip from Winnipeg to San José?
What’s the top layover airport for flights from Winnipeg to San José?
Share of one-stop round-trip flights from Winnipeg to San José chosen by Cheapflights users in the past 12 months, using the same layover each way.
Toronto (YYZ) – chosen by Cheapflights users on 83% of one-stop itineraries from Winnipeg to San José on Cheapflights.
What’s the cheapest layover airport for flights from Winnipeg to San José?
Average round-trip fare for 1-stop flights from Winnipeg to San José, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of C$ 1,083.
What’s the fastest layover option from Winnipeg to San José?
Shortest average travel time for 1-stop one-way flights from Winnipeg to San José, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Toronto (YYZ) have the shortest average one-way travel time for 1-stop routes: 11h 01m.
Which airport typically offers the quickest layover for flights from Winnipeg to San José?
Average layover duration for 1-stop one-way flights from Winnipeg to San José, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 2h 56m.
Reviews of airlines servicing San José
Get insights into the airlines that provide service to San José. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San José. Reviews last updated 15 December 2025.
See what other customers who have flown with United Airlines,Air Canada, andAvianca 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.
Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Related info for your journey
Find useful and relevant information for your journey from Winnipeg to San José. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
How long is the flight from Winnipeg to San José?
Airlines like United Airlines fly from Winnipeg to San José in about 27h 56m. 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 are the cheapest airlines flying from Winnipeg to San José round-trip?
United Airlines, at C$ 656, was found to be the cheapest airline from Winnipeg to San José.Alternate airlines to your destination round-trip include Air Canada and Avianca. Users have found that United Airlines is 42% cheaper than the other options available to this destination.
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.
What is the cheapest month to book a flight from Winnipeg to San José?
Currently, April is the cheapest month in which you can book a flight from Winnipeg to San José (average of C$ 651). Flying from Winnipeg to San José in June is currently the most expensive (average of C$ 953). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Browse through other flights departing from Winnipeg. Flights are based on user searches made on Cheapflights and were last updated on 15 December 2025.
Explore flights to San José departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 15 December 2025.
Discover the top 3 airlines that operate flights from Winnipeg to San José. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 15 December 2025.
Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.
How does Cheapflights help users find flights from Winnipeg to San José?
900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to San José from Winnipeg today with Cheapflights!
Why should you use Cheapflights to find cheap flight tickets from Winnipeg to San José?
Cheapflights simply makes it quick and affordable to book flights from Winnipeg to San José by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.
Can Cheapflights find flights from Winnipeg to San José with no change fees?
Users can book flights with no change fees policies with our dedicated filters. Book flights from Winnipeg to San José flexibly with Cheapflights today.
Can Cheapflights notify me if prices for flights from Winnipeg to San José become cheaper?
Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!
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