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Cheap flights from Winnipeg to Puerto Rico from C$ 527

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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
19 Nov — 26 Nov1
1 adult
1 adult, Economy

Find flight deals from Winnipeg to Puerto Rico

Enter your travel dates to find the best prices.

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 20 October 2025.

Fri 24/109:00 a.m.YWG - SJU
1 stop11h 59mWestJet
Mon 2/23:55 p.m.SJU - YWG
2 stops21h 37mWestJet
Deal found 19/10C$ 849
Fri 24/104:25 p.m.YWG - SJU
2 stops18h 35mUnited Airlines
Sun 1/22:05 a.m.SJU - YWG
2 stops23h 49mUnited Airlines
Deal found 19/10C$ 1,091
Sat 27/1212:20 p.m.YWG - SJU
2 stops27h 10mWestJet
Sat 3/13:30 p.m.SJU - YWG
1 stop25h 37mWestJet
Deal found 18/10C$ 1,194
Fri 24/105:40 p.m.YWG - SJU
1 stop20h 31mMultiple Airlines
Mon 2/211:05 a.m.SJU - YWG
1 stop32h 21mMultiple Airlines
Deal found 19/10C$ 1,233

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 20 October 2025.

Round-trip from

C$ 620

One-way from

C$ 527

Popular in

December

Cheapest in

April

Average price

C$ 1,079
24/1-2/2
  • 24/1-2/2
  • 5 total stops
  • 52h 40m total
  • Winnipeg to Puerto Rico
Search Deals
WestJet
  • WestJet
  • 3/4
  • 1 total stop
  • 13h 28m total
  • Winnipeg to Puerto Rico
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 145 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 20 October 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

Sat 24/1

9:00 p.m.-3:06 p.m.

2 stops16h 06m

San Juan Luis Munoz Marin Intl

Mon 2/2

4:11 p.m.-12:40 a.m.

2 stops34h 29m

C$ 625

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 28/1

6:55 p.m.-7:23 p.m.

3 stops22h 28m

San Juan Luis Munoz Marin Intl

Mon 16/2

8:28 p.m.-3:30 p.m.

2 stops21h 02m

C$ 900

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 3/3

5:00 a.m.-11:49 p.m.

2 stops16h 49m

San Juan Luis Munoz Marin Intl

Wed 4/3

7:30 a.m.-3:09 p.m.

1 stop9h 39m

C$ 908

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 28/1

6:55 p.m.-7:23 p.m.

3 stops22h 28m

San Juan Luis Munoz Marin Intl

Sun 15/2

5:28 p.m.-10:40 p.m.

3 stops31h 12m

C$ 915

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 3/4

7:30 a.m.-9:58 p.m.

1 stop13h 28m

C$ 527

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 3/4

12:10 p.m.-8:36 a.m.

3 stops19h 26m

C$ 883

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/10

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, May is the cheapest month in which you can book a flight from Winnipeg to Puerto Rico (average of C$ 412). Flying from Winnipeg to Puerto Rico in October is currently the most expensive (average of C$ 856). 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 20 October 2025.

When flying from Winnipeg to Puerto Rico, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 13% versus a flight in the morning.

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 20 October 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
8,991 reviews
Check prices

Comfort

7.3

Boarding

7.7

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,991 reviews
United Airlines
7.4
Good
8,991 reviews
Check prices

Comfort

7.3

Boarding

7.7

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
WestJet
7.2
Good
3,129 reviews
United Airlines
7.4
Good
8,991 reviews
Check prices

Comfort

7.3

Boarding

7.7

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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, May is the cheapest month in which you can book a flight from Winnipeg to Puerto Rico (average of C$ 412). Flying from Winnipeg to Puerto Rico in October is currently the most expensive (average of C$ 856). 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 20 October 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 510AverageC$ 780FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 757AverageC$ 884FlexibilityNo 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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