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Cheap flights from Winnipeg to Puerto Rico from C$ 375

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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
1 Jul — 8 Jul1
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 26 June 2025.

Popular in

October

Cheapest in

April

Average price

C$ 824
Highest demand for flights based on searches. 7% potential increase in price (C$ 91 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
Search Deals

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 26 June 2025.

Fri 7/117:30 a.m.YWG - SJU
1 stop13h 47mWestJet
Sun 16/117:00 a.m.SJU - YWG
2 stops38h 10mWestJet
Deal found 24/6C$ 931
Fri 7/115:15 a.m.YWG - SJU
2 stops13h 45mUnited Airlines
Sat 15/112:05 a.m.SJU - YWG
2 stops18h 23mUnited Airlines
Deal found 24/6C$ 1,027
Fri 7/117:00 a.m.YWG - SJU
1 stop14h 54mMultiple Airlines
Sat 15/113:06 a.m.SJU - YWG
2 stops14h 04mMultiple Airlines
Deal found 24/6C$ 1,188

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 26 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 7/11

7:30 a.m.-11:17 p.m.

1 stop13h 47m

San Juan Luis Munoz Marin Intl

Sun 16/11

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

2 stops38h 10m

C$ 931

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 7/11

5:15 a.m.-9:00 p.m.

2 stops13h 45m

San Juan Luis Munoz Marin Intl

Sat 15/11

2:05 a.m.-6:28 p.m.

2 stops18h 23m

C$ 1,027

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 7/11

7:00 a.m.-11:54 p.m.

1 stop14h 54m

San Juan Luis Munoz Marin Intl

Sat 15/11

3:06 a.m.-3:10 p.m.

2 stops14h 04m

C$ 1,188

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 9/8

12:26 p.m.-4:31 p.m.

2 stops27h 05m

C$ 375

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 9/8

5:45 p.m.-9:09 p.m.

3 stops50h 24m

C$ 383

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 9/8

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

1 stop8h 34m

C$ 525

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/6

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 26 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.

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 26 June 2025.
Read reviews from past customers who have flown Delta and United Airlines 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.
Delta
8.0
Very good
7,964 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

ATL - JNB

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Delta
8.0
Very good
7,964 reviews
Delta
8.0
Very good
7,964 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

ATL - JNB

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
United Airlines
7.4
Good
8,838 reviews
Delta
8.0
Very good
7,964 reviews
Check prices

Boarding

8.2

Comfort

7.9

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

ATL - JNB

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

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

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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 26 June 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 465AverageC$ 762FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 738AverageC$ 837FlexibilityNo 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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