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Cheap flights from Winnipeg to Costa Rica from C$ 307

YWG — SJO
27 Oct — 3 Nov1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Costa Rica

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Costa Rica

Fri 30/1012:40 a.m. -
Nonstop6h 20m
Sat 7/117:50 a.m. -
Nonstop6h 25m
Deal found 25/9C$ 370
Fri 30/1012:40 a.m. -
Nonstop6h 20m
Fri 6/117:40 a.m. -
1 stop26h 40m
Deal found 22/9C$ 406
Fri 30/1012:40 a.m. -
Nonstop6h 20m
Thu 5/117:40 a.m. -
2 stops16h 19m
Deal found 22/9C$ 409
Fri 30/1012:40 a.m. -
Nonstop6h 20m
Wed 4/117:40 a.m. -
2 stops14h 35m
Deal found 22/9C$ 417
Mon 28/122:15 p.m. -
2 stops32h 17m
Tue 12/11:15 a.m. -
2 stops21h 18m
Deal found 26/9C$ 786
Sat 24/107:00 a.m. -
2 stops28h 25m
Sat 31/101:25 p.m. -
2 stops22h 58m
Deal found 26/9C$ 795
Sun 25/108:40 a.m. -
2 stops35h 59m
Sun 1/117:30 a.m. -
2 stops52h 53m
Deal found 25/9C$ 796
Sun 29/118:40 a.m. -
2 stops26h 45m
Thu 3/128:45 a.m. -
2 stops36h 10m
Deal found 25/9C$ 802
Sat 7/112:15 p.m. -
2 stops21h 10m
Mon 16/1112:35 p.m. -
2 stops23h 48m
Deal found 25/9C$ 814
Sun 8/112:15 p.m. -
2 stops23h 07m
Tue 17/118:45 a.m. -
2 stops27h 38m
Deal found 24/9C$ 816
Sun 29/118:05 a.m. -
1 stop15h 45m
Thu 3/128:45 a.m. -
2 stops33h 40m
Deal found 22/9C$ 826
Sun 11/107:00 a.m. -
2 stops37h 37m
Thu 15/107:55 a.m. -
2 stops37h 38m
Deal found 25/9C$ 836

Find flight deals from Winnipeg to Costa Rica

Round-trip from

C$ 370

One-way from

C$ 307

Popular in

December

Cheapest in

October

Average price

C$ 583

Good round-trip deal

C$ 397 or less
WestJet
  • WestJet
  • 30/10-7/11
  • Nonstop
  • 12h 45m total
  • Winnipeg to Costa Rica
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WestJet
  • WestJet
  • 16/11-31/12
  • 1 total stop
  • 27h 00m total
  • Winnipeg to Costa Rica
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 322 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease (C$ 102 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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Price to beat on a round-trip flight from Winnipeg to Costa Rica.
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Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegLiberia

YWG Winnipeg - LIR Liberia

YWGLIR

Winnipeg

Mon 16/11

9:35 a.m.-12:35 p.m.

1 stop27h 00m

Liberia

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 307

WinnipegLiberia

YWG Winnipeg - LIR Liberia

YWGLIR

Winnipeg

Tue 10/11

11:00 a.m.-3:18 p.m.

1 stop28h 18m

Liberia

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 335

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 1/3

7:00 a.m.-8:39 p.m.

2 stops37h 39m

San José Juan Santamaria Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 427

WinnipegLiberia

YWG Winnipeg - LIR Liberia

YWGLIR

Winnipeg

Mon 1/2

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

2 stops24h 10m

Liberia

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 433

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Tue 10/11

2:15 p.m.-8:39 p.m.

2 stops30h 24m

San José Juan Santamaria Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 435

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Mon 2/11

8:40 a.m.-1:22 p.m.

2 stops28h 42m

San José Juan Santamaria Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 437
Quickest round-trip

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sat 5/12

8:40 a.m.-6:25 a.m.

2 stops21h 45m

San José Juan Santamaria Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 443

WinnipegSan José

YWG Winnipeg - SJO San José Juan Santamaria Intl

YWGSJO

Winnipeg

Sat 5/12

6:55 p.m.-10:30 p.m.

1 stop27h 35m

San José Juan Santamaria Intl

Wed 31/12

12:00 a.m.-12:00 a.m.

Nonstop0h 00m

C$ 461

WinnipegLiberia

YWG Winnipeg - LIR Liberia

YWGLIR

Winnipeg

Mon 18/1

7:00 a.m.-1:10 p.m.

2 stops30h 10m

Liberia

Mon 8/2

8:45 a.m.-10:33 p.m.

2 stops37h 48m

C$ 512

WinnipegLiberia

YWG Winnipeg - LIR Liberia

YWGLIR

Winnipeg

Tue 19/1

7:00 a.m.-1:10 p.m.

2 stops54h 10m

Liberia

Wed 3/2

1:00 p.m.-10:33 p.m.

2 stops33h 33m

C$ 513

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/9

Showing 1-10 of 29 resultsSorted by cheapest first
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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

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, April is the cheapest month in which you can book a flight from Winnipeg to Costa Rica (average of C$ 657). Flying from Winnipeg to Costa Rica in December is currently the most expensive (average of C$ 1,582). 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.

How far ahead should I book a flight from Winnipeg to Costa Rica?

The price you pay for your flight from Winnipeg to Costa Rica may vary depending on when you book. For the best chance of a lower fare, look to book 25 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

Reviews of airlines servicing Costa Rica

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
463 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Porter Airlines
8.0
Very good
463 reviews
Porter Airlines
8.0
Very good
463 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
United Airlines
7.4
Good
10,243 reviews
Porter Airlines
8.0
Very good
463 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
WestJet
7.2
Good
3,450 reviews
Porter Airlines
8.0
Very good
463 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Air Canada
7.1
Good
11,696 reviews
Porter Airlines
8.0
Very good
463 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Related info for your journey

  • 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 30h 10m. Fly via United Airlines or WestJet to get the fastest option. Winnipeg and Costa Rica are separated by a distance of 4498 km. This flight may include one or multiple stops.

  • 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, April is the cheapest month in which you can book a flight from Winnipeg to Costa Rica (average of C$ 657). Flying from Winnipeg to Costa Rica in December is currently the most expensive (average of C$ 1,582). 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

Top 4 airlines flying from Winnipeg to Costa Rica

AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 342AverageC$ 627FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 411AverageC$ 960FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Porter AirlinesCheapestC$ 431AverageC$ 686FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 511AverageC$ 997FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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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