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Cheap flights from Winnipeg to Puerto Rico from C$ 395

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 27/7. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
17 Jun — 24 Jun1
1 adult

Cheap flight deals from Winnipeg to Puerto Rico

Keep the following information in mind while searching for Winnipeg to Puerto Rico flight deals. Data was last updated 12 June 2025.

Round-trip from

C$ 572

One-way from

C$ 395

Popular in

October

Cheapest in

April

Average price

C$ 757
11/7-17/7
  • 11/7-17/7
  • 3 total stops
  • 44h 08m total
  • Winnipeg to Puerto Rico
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27/7
  • 27/7
  • 3 total stops
  • 56h 24m total
  • Winnipeg to Puerto Rico
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 98 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 41 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
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Find flight deals from Winnipeg to Puerto Rico

Cheapest flights from Winnipeg to Puerto Rico
Explore the most affordable flight options available from Winnipeg to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 12 June 2025.

Fri 11/79:00 a.m.YWG - SJU
1 stop29h 25mMultiple Airlines
Thu 17/72:40 a.m.SJU - YWG
2 stops14h 43mMultiple Airlines
Deal found 11/6C$ 572
Fri 11/78:35 a.m.YWG - SJU
2 stops14h 24mDelta
Fri 18/76:15 a.m.SJU - YWG
2 stops14h 55mDelta
Deal found 11/6C$ 630
Sat 18/107:55 a.m.YWG - SJU
2 stops27h 39mAir Canada
Sun 26/102:45 p.m.SJU - YWG
2 stops25h 28mAir Canada
Deal found 10/6C$ 660
Sat 13/128:00 p.m.YWG - SJU
2 stops19h 10mWestJet
Mon 22/121:10 p.m.SJU - YWG
2 stops32h 00mWestJet
Deal found 11/6C$ 861
Sat 18/107:40 a.m.YWG - SJU
2 stops15h 17mUnited Airlines
Sat 25/101:05 a.m.SJU - YWG
2 stops15h 53mUnited Airlines
Deal found 10/6C$ 947
Thu 21/86:35 p.m.YWG - SJU
2 stops21h 15mAvianca
Mon 25/82:10 p.m.SJU - YWG
3 stops27h 08mAvianca
Deal found 11/6C$ 1,807

Cheapflights Fare Finder

Customize your flight search to find flights from Winnipeg to Puerto Rico 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 12 June 2025.
Use the filters below to find and compare flights from Winnipeg to Puerto Rico that are best for you.

Fly from

Winnipeg

Fly to

Puerto Rico

Route

Depart

Return

Price

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 11/7

9:00 a.m.-3:25 p.m.

1 stop29h 25m

San Juan Luis Munoz Marin Intl

Thu 17/7

2:40 a.m.-4:23 p.m.

2 stops14h 43m

C$ 572

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 11/7

8:35 a.m.-11:59 p.m.

2 stops14h 24m

San Juan Luis Munoz Marin Intl

Fri 18/7

6:15 a.m.-8:10 p.m.

2 stops14h 55m

C$ 630

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 18/10

7:55 a.m.-12:34 p.m.

2 stops27h 39m

San Juan Luis Munoz Marin Intl

Sun 26/10

2:45 p.m.-3:13 p.m.

2 stops25h 28m

C$ 660

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 21/8

5:45 p.m.-4:36 p.m.

2 stops21h 51m

San Juan Luis Munoz Marin Intl

Mon 25/8

7:30 a.m.-9:43 a.m.

2 stops27h 13m

C$ 902

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 18/10

7:40 a.m.-11:57 p.m.

2 stops15h 17m

San Juan Luis Munoz Marin Intl

Sat 25/10

1:05 a.m.-3:58 p.m.

2 stops15h 53m

C$ 947

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 21/8

6:35 p.m.-4:50 p.m.

2 stops21h 15m

San Juan Luis Munoz Marin Intl

Mon 25/8

2:10 p.m.-4:18 p.m.

3 stops27h 08m

C$ 1,807

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 25/7

2:20 p.m.-11:54 p.m.

1 stop8h 34m

C$ 451

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 25/7

6:30 a.m.-10:23 p.m.

2 stops14h 53m

C$ 477

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

Best time to book a flight from Winnipeg to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico 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 Puerto Rico

What is the cheapest month to book a flight from Winnipeg to Puerto Rico?

Currently, April is the cheapest month in which you can book a flight from Winnipeg to Puerto Rico (average of C$ 254). Flying from Winnipeg to Puerto Rico in July is currently the most expensive (average of C$ 580). 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 PR?

Find hourly flight availability from Winnipeg to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 12 June 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Puerto Rico as you normally would.

Rainfall in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Puerto Rico ranges from 55.0 - 156.0 mm per month. November is typically the wettest month, when rainfall can reach 156.0 mm. March is typically the driest time to visit Puerto Rico when rainfall is around 55.0 mm.

Temperature in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Puerto Rico, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 28.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 25.0 C).

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated 12 June 2025.
Delta
8.0
Very good
7,950 reviews
Check prices

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Anonymous,Sep 2023

AVL - LGA

Landing in Syracuse was ruff no bad weather just bad piloting. A/C barely. Working from LGA to Syracuse.
Delta
8.0
Very good
7,950 reviews
Delta
8.0
Very good
7,950 reviews
Check prices

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Anonymous,Sep 2023

AVL - LGA

Landing in Syracuse was ruff no bad weather just bad piloting. A/C barely. Working from LGA to Syracuse.
United Airlines
7.4
Good
8,790 reviews
Delta
8.0
Very good
7,950 reviews
Check prices

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Anonymous,Sep 2023

AVL - LGA

Landing in Syracuse was ruff no bad weather just bad piloting. A/C barely. Working from LGA to Syracuse.
WestJet
7.2
Good
2,868 reviews
Delta
8.0
Very good
7,950 reviews
Check prices

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Anonymous,Sep 2023

AVL - LGA

Landing in Syracuse was ruff no bad weather just bad piloting. A/C barely. Working from LGA to Syracuse.
Air Canada
7.1
Good
9,531 reviews
Delta
8.0
Very good
7,950 reviews
Check prices

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Anonymous,Sep 2023

AVL - LGA

Landing in Syracuse was ruff no bad weather just bad piloting. A/C barely. Working from LGA to Syracuse.
Avianca
6.7
Okay
2,345 reviews
Delta
8.0
Very good
7,950 reviews
Check prices

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Anonymous,Sep 2023

AVL - LGA

Landing in Syracuse was ruff no bad weather just bad piloting. A/C barely. Working from LGA to Syracuse.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Puerto Rico. 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 Puerto Rico?

    Most people fly from Winnipeg (YWG) if they book a flight from Winnipeg to Puerto Rico. Winnipeg is conveniently located just 7.3 km from Winnipeg’s city centre.

  • Can I find deals for flights from Winnipeg to Puerto Rico that include hotel bookings?

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

  • How can I find direct flights from Winnipeg to Puerto Rico?

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

  • Can I find deals for business class flights from Winnipeg to Puerto Rico?

    Yes. Cheapflights offers flight deals from Winnipeg to Puerto Rico 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 Puerto Rico?

    Currently, April is the cheapest month in which you can book a flight from Winnipeg to Puerto Rico (average of C$ 254). Flying from Winnipeg to Puerto Rico in July is currently the most expensive (average of C$ 580). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 2 airlines flying from Winnipeg to Puerto Rico

Discover the top 2 airlines that operate flights from Winnipeg to Puerto Rico. 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 12 June 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 465AverageC$ 762FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 738AverageC$ 834FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Winnipeg to Puerto Rico?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Winnipeg to Puerto Rico. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Puerto Rico?

Millions of users choose and trust Cheapflights to book the best flight deals from Winnipeg to Puerto Rico for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Winnipeg to Puerto Rico with no change fees?

Yes, we can. To see specific flights from Winnipeg to Puerto Rico with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Winnipeg to Puerto Rico become cheaper?

Yes, Cheapflights offers price alerts on Winnipeg to Puerto Rico 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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