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Cheap flights from Winnipeg to Costa Rica from C$ 323

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 28/3. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJO
10 Dec — 17 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Costa Rica

Keep the following information in mind while searching for Winnipeg to Costa Rica flight deals. Data was last updated 10 November 2025.

Round-trip from

C$ 524

One-way from

C$ 327

Popular in

December

Cheapest in

July

Average price

C$ 1,345

Good round-trip deal

C$ 1,094 or less
5/12-10/12
  • 5/12-10/12
  • 3 total stops
  • 60h 03m total
  • Winnipeg to Costa Rica
Search Deals
30/1
  • 30/1
  • 2 total stops
  • 28h 52m total
  • Winnipeg to Costa Rica
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 317 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 63 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Winnipeg to Costa Rica.
Search Deals

Find flight deals from Winnipeg to Costa Rica

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Costa Rica
Explore the most affordable flight options available from Winnipeg to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 10 November 2025.

Fri 5/127:30 a.m.YWG - SJO
1 stop30h 22mMultiple Airlines
Wed 10/121:31 p.m.SJO - YWG
2 stops29h 41mMultiple Airlines
Deal found 10/11C$ 524
Sat 6/1212:20 p.m.YWG - SJO
2 stops48h 05mMultiple Airlines
Sat 13/123:07 p.m.SJO - YWG
1 stop24h 00mMultiple Airlines
Deal found 9/11C$ 565
Fri 5/124:25 p.m.YWG - LIR
2 stops45h 30mPorter Airlines
Thu 11/122:55 p.m.LIR - YWG
1 stop24h 35mPorter Airlines
Deal found 9/11C$ 739
Fri 5/125:00 a.m.YWG - LIR
1 stop9h 29mWestJet
Thu 11/123:20 p.m.LIR - YWG
1 stop20h 15mWestJet
Deal found 7/11C$ 740
Fri 5/127:05 p.m.YWG - LIR
1 stop19h 40mAir Canada
Thu 11/122:55 p.m.LIR - YWG
1 stop19h 21mAir Canada
Deal found 8/11C$ 805
Tue 9/122:20 p.m.YWG - SJO
2 stops30h 19mUnited Airlines
Tue 16/128:45 a.m.SJO - YWG
2 stops27h 12mUnited Airlines
Deal found 9/11C$ 823
Wed 17/128:40 a.m.YWG - LIR
2 stops26h 44mUnited Airlines
Sat 27/123:50 p.m.LIR - YWG
2 stops20h 07mUnited Airlines
Deal found 8/11C$ 840
Wed 17/129:05 a.m.YWG - LIR
2 stops21h 53mWestJet
Sat 27/127:00 a.m.LIR - YWG
Nonstop6h 27mWestJet
Deal found 8/11C$ 867

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Costa Rica 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 10 November 2025.
Use the filters below to find and compare flights from Winnipeg to Costa Rica that are best for you.

Fly from

Winnipeg

Fly to

Costa Rica

Route

Depart

Return

Price

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Fri 5/12

7:30 a.m.-1:52 p.m.

1 stop30h 22m

San José Juan Santamaria Intl

Wed 10/12

1:31 p.m.-7:12 p.m.

2 stops29h 41m

C$ 524

WinnipegLiberia

YWG - LIR

YWGLIR

Winnipeg

Mon 23/3

9:00 p.m.-12:55 p.m.

2 stops16h 55m

Liberia

Mon 30/3

3:00 p.m.-7:09 p.m.

2 stops27h 09m

C$ 591

WinnipegLiberia

YWG - LIR

YWGLIR

Winnipeg

Sat 31/1

2:20 p.m.-1:10 p.m.

2 stops22h 50m

Liberia

Sat 7/2

8:35 a.m.-11:57 a.m.

2 stops27h 22m

C$ 649

WinnipegLiberia

YWG - LIR

YWGLIR

Winnipeg

Fri 9/1

2:20 p.m.-6:37 p.m.

2 stops28h 17m

Liberia

Fri 23/1

2:01 p.m.-11:57 a.m.

1 stop21h 56m

C$ 649

WinnipegLiberia

YWG - LIR

YWGLIR

Winnipeg

Thu 22/1

2:20 p.m.-12:55 p.m.

1 stop22h 35m

Liberia

Sat 7/2

8:35 a.m.-11:57 a.m.

2 stops27h 22m

C$ 649

WinnipegLiberia

YWG - LIR

YWGLIR

Winnipeg

Sun 12/4

8:45 a.m.-12:10 p.m.

2 stops28h 25m

Liberia

Thu 16/4

1:20 p.m.-8:52 p.m.

2 stops30h 32m

C$ 649

WinnipegLiberia

YWG - LIR

YWGLIR

Winnipeg

Sat 7/2

2:20 p.m.-12:55 p.m.

1 stop22h 35m

Liberia

Sat 14/2

4:53 p.m.-11:57 a.m.

2 stops19h 04m

C$ 649

WinnipegLiberia

YWG - LIR

YWGLIR

Winnipeg

Tue 13/1

2:20 p.m.-1:10 p.m.

2 stops22h 50m

Liberia

Fri 13/2

8:35 a.m.-11:57 a.m.

2 stops27h 22m

C$ 649

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Sun 1/2

2:20 p.m.-8:39 p.m.

2 stops30h 19m

San José Juan Santamaria Intl

Thu 12/2

2:05 p.m.-11:57 a.m.

1 stop21h 52m

C$ 671

WinnipegSan José

YWG - SJO

YWGSJO

Winnipeg

Tue 3/3

2:20 p.m.-1:15 p.m.

2 stops22h 55m

San José Juan Santamaria Intl

Tue 10/3

1:20 p.m.-11:39 a.m.

2 stops21h 19m

C$ 671

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 26 results
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Best time to book a flight from Winnipeg to Costa Rica

Have a flexible travel schedule? Discover the best time to fly to Costa Rica 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 Costa Rica

What is the cheapest month to book a flight from Winnipeg to Costa Rica?

Currently, June is the cheapest month in which you can book a flight from Winnipeg to Costa Rica (average of C$ 404). Flying from Winnipeg to Costa Rica in July is currently the most expensive (average of C$ 680). 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 CR?

Find hourly flight availability from Winnipeg to Costa Rica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 10 November 2025.

It’s optimal to fly from Winnipeg to Costa Rica at noon. By choosing this option you can save up to 36% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Winnipeg to Costa Rica?

Use this chart to determine the cheapest time to fly round-trip from Winnipeg to Costa Rica. Price data was last updated on 16 December 2024.

Travelers seeking maximum savings on their Winnipeg to Costa Rica flight should consider departing on Tuesday mornings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Costa Rica

Get insights into the airlines that provide service to Costa Rica. 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 Costa Rica. Reviews last updated 10 November 2025.
Check out reviews from past customers who have flown with Porter Airlines,United Airlines, andWestJet from Winnipeg to Costa Rica to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
389 reviews
Check prices

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Porter Airlines
8.0
Very good
389 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
United Airlines
7.4
Good
9,012 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
WestJet
7.2
Good
3,159 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Air Canada
7.1
Good
10,437 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Avianca
6.6
Okay
2,473 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Overall

8.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Costa Rica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Winnipeg to Costa Rica?

    Winnipeg (YWG) is the airport you will fly out of if you book a flight from Winnipeg to Costa Rica. It is only a 7.3 km journey to Winnipeg (YWG) from Winnipeg’s city centre.

  • How long is the flight from Winnipeg to Costa Rica?

    There are many flights that can get you from Winnipeg to Costa Rica in 22h 50m. Fly via United Airlines to get the fastest option. Winnipeg and Costa Rica are separated by a distance of 4498 km.

  • What are the cheapest airlines to fly from Winnipeg to Costa Rica one-way?

    One-way options have recently been found by users for as low as C$ 323 on WestJet. Other airlines that offer cheap prices include Porter Airlines from C$ 402 and United Airlines from C$ 438 one-way.

  • Can I find deals for flights from Winnipeg to Costa Rica that include hotel bookings?

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

  • How can I find direct flights from Winnipeg to Costa Rica?

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

  • Can I find deals for business class flights from Winnipeg to Costa Rica?

    Yes. Cheapflights offers flight deals from Winnipeg to Costa Rica 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 Costa Rica?

    Currently, June is the cheapest month in which you can book a flight from Winnipeg to Costa Rica (average of C$ 404). Flying from Winnipeg to Costa Rica in July is currently the most expensive (average of C$ 680). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top 5 airlines flying from Winnipeg to Costa Rica

Discover the top 5 airlines that operate flights from Winnipeg to Costa Rica. 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 10 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 393AverageC$ 746FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 473AverageC$ 777FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 600AverageC$ 973FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 1,021AverageC$ 1,455FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
AviancaCheapestC$ 1,252AverageC$ 1,613FlexibilityNo cancel feeOn-time71%
Search Avianca flights

Fly with Cheapflights

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 Costa Rica?

Deals for Winnipeg to Costa Rica flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Costa Rica?

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 Costa Rica from Winnipeg.

Can Cheapflights find flights from Winnipeg to Costa Rica with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Winnipeg to Costa Rica, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Winnipeg to Costa Rica become cheaper?

Yes, Cheapflights offers price alerts on Winnipeg to Costa Rica flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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