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Cheap flights from Winnipeg to Puerto Rico from C$ 338

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 24/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
27 Aug — 3 Sep1
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 22 August 2025.

Round-trip from

C$ 774

One-way from

C$ 338

Popular in

August

Cheapest in

April

Average price

C$ 1,194
Delta
  • Delta
  • 8/1-14/1
  • 4 total stops
  • 51h 44m total
  • Winnipeg to Puerto Rico
Search Deals
24/10
  • 24/10
  • 3 total stops
  • 28h 12m total
  • Winnipeg to Puerto Rico
Search Deals
Highest demand for flights based on searches. 1% potential increase in price (C$ 15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 22 August 2025.

Thu 27/115:00 a.m.YWG - SJU
2 stops16h 17mWestJet
Sat 6/127:30 a.m.SJU - YWG
2 stops19h 12mWestJet
Deal found 20/8C$ 843
Thu 27/1112:20 p.m.YWG - SJU
2 stops12h 34mMultiple Airlines
Sat 6/123:59 p.m.SJU - YWG
1 stop25h 08mMultiple Airlines
Deal found 20/8C$ 856
Fri 3/1010:45 a.m.YWG - SJU
2 stops24h 03mWestJet
Mon 6/107:00 a.m.SJU - YWG
2 stops31h 43mWestJet
Deal found 20/8C$ 882
Thu 27/118:40 a.m.YWG - SJU
1 stop31h 45mUnited Airlines
Fri 5/122:05 a.m.SJU - YWG
2 stops12h 34mUnited Airlines
Deal found 20/8C$ 960
Fri 3/102:20 p.m.YWG - SJU
1 stop23h 24mUnited Airlines
Sun 5/101:05 a.m.SJU - YWG
2 stops23h 20mUnited Airlines
Deal found 20/8C$ 968
Fri 19/128:00 a.m.YWG - SJU
2 stops33h 08mMultiple Airlines
Sat 10/17:52 p.m.SJU - YWG
1 stop21h 15mMultiple Airlines
Deal found 20/8C$ 1,132
Fri 19/128:05 p.m.YWG - SJU
2 stops25h 54mWestJet
Sat 10/16:15 a.m.SJU - YWG
2 stops38h 57mWestJet
Deal found 20/8C$ 1,183
Fri 19/128:40 a.m.YWG - SJU
2 stops19h 31mUnited Airlines
Fri 9/12:05 a.m.SJU - YWG
2 stops23h 39mUnited Airlines
Deal found 20/8C$ 1,496
Sat 23/82:35 p.m.YWG - SJU
2 stops24h 52mWestJet
Mon 1/97:00 a.m.SJU - YWG
2 stops27h 41mWestJet
Deal found 21/8C$ 1,871

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 22 August 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

Thu 8/1

5:38 p.m.-11:49 p.m.

2 stops28h 11m

San Juan Luis Munoz Marin Intl

Wed 14/1

2:10 p.m.-11:43 a.m.

2 stops23h 33m

C$ 774

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 7/1

7:30 a.m.-5:19 p.m.

1 stop7h 49m

San Juan Luis Munoz Marin Intl

Wed 14/1

3:30 p.m.-7:12 p.m.

2 stops29h 42m

C$ 796

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 8/1

8:05 p.m.-2:15 p.m.

2 stops16h 10m

San Juan Luis Munoz Marin Intl

Wed 14/1

7:30 a.m.-3:07 p.m.

1 stop9h 37m

C$ 833

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 27/11

5:00 a.m.-11:17 p.m.

2 stops16h 17m

San Juan Luis Munoz Marin Intl

Sat 6/12

7:30 a.m.-12:42 a.m.

2 stops19h 12m

C$ 843

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 27/11

12:20 p.m.-2:54 a.m.

2 stops12h 34m

San Juan Luis Munoz Marin Intl

Sat 6/12

3:59 p.m.-3:07 p.m.

1 stop25h 08m

C$ 856

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 3/10

10:45 a.m.-11:48 a.m.

2 stops24h 03m

San Juan Luis Munoz Marin Intl

Mon 6/10

7:00 a.m.-1:43 p.m.

2 stops31h 43m

C$ 882

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 4/2

7:30 a.m.-5:15 p.m.

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Sun 15/2

6:15 a.m.-3:09 p.m.

1 stop10h 54m

C$ 943

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 27/11

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

1 stop31h 45m

San Juan Luis Munoz Marin Intl

Fri 5/12

2:05 a.m.-12:39 p.m.

2 stops12h 34m

C$ 960

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 3/10

4:25 p.m.-8:38 p.m.

2 stops27h 13m

San Juan Luis Munoz Marin Intl

Sun 5/10

1:05 a.m.-11:25 p.m.

2 stops23h 20m

C$ 968

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 24/10

9:00 a.m.-2:12 p.m.

3 stops28h 12m

C$ 338

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/8

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 22 August 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.

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 22 August 2025.
Read reviews from past customers who have flown United Airlines and WestJet from Winnipeg to Puerto Rico. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,934 reviews
Check prices

Overall

7.4

Food

6.6

Comfort

7.3

Boarding

7.7

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2024

YVR - SFO

It was a good experience. The flight took 45 minutes longer to fly and all passengers had to wait inside the plane till the technical issue was fixed. Overall it was a good experience.
United Airlines
7.4
Good
8,934 reviews
United Airlines
7.4
Good
8,934 reviews
Check prices

Overall

7.4

Food

6.6

Comfort

7.3

Boarding

7.7

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2024

YVR - SFO

It was a good experience. The flight took 45 minutes longer to fly and all passengers had to wait inside the plane till the technical issue was fixed. Overall it was a good experience.
WestJet
7.2
Good
3,044 reviews
United Airlines
7.4
Good
8,934 reviews
Check prices

Overall

7.4

Food

6.6

Comfort

7.3

Boarding

7.7

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2024

YVR - SFO

It was a good experience. The flight took 45 minutes longer to fly and all passengers had to wait inside the plane till the technical issue was fixed. Overall it was a good experience.

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.

  • How long is the flight from Winnipeg to Puerto Rico?

    A quick flight from Winnipeg to Puerto Rico can take about 7h 49m. Delta provides one of the quickest options available for as low as C$ 796. The distance between Winnipeg and Puerto Rico is about 4461 km. This flight may include one or multiple stops.

  • 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

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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 22 August 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 500AverageC$ 774FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 750AverageC$ 874FlexibilityNo cancel feeOn-time60%
Search WestJet 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 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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