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Cheap flights from Winnipeg to Puerto Rico from C$ 499

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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
29 Mar — 5 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap 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 27 February 2026.

Mon 13/48:00 a.m.
YWG
-
SJU
1 stop9h 55m
Multiple Airlines
Wed 22/43:36 p.m.
SJU
-
YWG
2 stops28h 33m
Multiple Airlines
Deal found 25/2C$ 521
Wed 15/47:30 a.m.
YWG
-
SJU
1 stop29h 38m
Multiple Airlines
Wed 22/43:36 p.m.
SJU
-
YWG
2 stops28h 33m
Multiple Airlines
Deal found 25/2C$ 681
Fri 20/38:20 p.m.
YWG
-
SJU
2 stops22h 35m
Multiple Airlines
Fri 27/36:30 a.m.
SJU
-
YWG
1 stop19h 56m
Multiple Airlines
Deal found 26/2C$ 740
Tue 17/38:05 p.m.
YWG
-
SJU
2 stops21h 50m
Multiple Airlines
Tue 24/312:05 p.m.
SJU
-
YWG
1 stop28h 04m
Multiple Airlines
Deal found 26/2C$ 773

Find 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 27 February 2026.

Round-trip from

C$ 521

One-way from

C$ 499

Popular in

December

Cheapest in

April

Average price

C$ 1,052
13/4-22/4
  • 13/4-22/4
  • 3 total stops
  • 38h 28m total
  • Winnipeg to Puerto Rico
Search Deals
WestJet
  • WestJet
  • 12/4
  • 1 total stop
  • 28h 55m total
  • Winnipeg to Puerto Rico
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 190 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 51 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 27 February 2026.
Use the filters below to find and compare flights from Winnipeg to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 2/6

6:15 a.m.-8:30 p.m.

2 stops13h 15m

San Juan Luis Munoz Marin Intl

Sat 20/6

7:30 a.m.-12:55 a.m.

2 stops18h 25m

C$ 922

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 2/6

8:45 a.m.-5:38 p.m.

1 stop31h 53m

San Juan Luis Munoz Marin Intl

Thu 18/6

1:00 a.m.-2:25 p.m.

2 stops14h 25m

C$ 979

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 25/3

6:15 a.m.-10:45 p.m.

2 stops15h 30m

San Juan Luis Munoz Marin Intl

Sun 5/4

2:00 p.m.-11:32 a.m.

1 stop22h 32m

C$ 1,003

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 2/6

7:00 a.m.-8:34 p.m.

1 stop12h 34m

San Juan Luis Munoz Marin Intl

Sat 20/6

7:20 a.m.-10:33 p.m.

2 stops16h 13m

C$ 1,052

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 15/4

7:30 a.m.-8:24 p.m.

1 stop11h 54m

San Juan Luis Munoz Marin Intl

Wed 22/4

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

1 stop9h 54m

C$ 1,169

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 26/3

12:20 p.m.-8:18 p.m.

2 stops30h 58m

San Juan Luis Munoz Marin Intl

Thu 2/4

2:44 p.m.-11:32 a.m.

2 stops21h 48m

C$ 1,242

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 25/3

7:30 a.m.-8:18 p.m.

1 stop11h 48m

San Juan Luis Munoz Marin Intl

Sun 5/4

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

1 stop9h 54m

C$ 1,390

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 26/3

2:20 p.m.-8:00 p.m.

1 stop28h 40m

San Juan Luis Munoz Marin Intl

Wed 1/4

1:00 a.m.-8:57 p.m.

2 stops20h 57m

C$ 1,487

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 12/4

7:30 a.m.-1:25 p.m.

1 stop28h 55m

C$ 499

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 3/4

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

2 stops23h 34m

C$ 546

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/2

Showing 1-10 of 12 resultsSorted by cheapest first
1
2

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
No data available for this route at this time. Please check back soon.

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 27 February 2026.
Read reviews from past customers who have flown 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.
WestJet
7.2
Good
3,276 reviews
Check prices

Boarding

7.4

Comfort

7.0

Crew

7.9

Entertainment

6.1

Food

6.2

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..
WestJet
7.2
Good
3,276 reviews
WestJet
7.2
Good
3,276 reviews
Check prices

Boarding

7.4

Comfort

7.0

Crew

7.9

Entertainment

6.1

Food

6.2

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..

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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Winnipeg to Puerto Rico

Discover the top airline 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 27 February 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 713AverageC$ 888FlexibilityNo 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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