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Cheap flights from Winnipeg to Puerto Rico from C$ 407

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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
12 Jun — 19 Jun1
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 13 May 2026.

Tue 22/97:00 a.m.
YWG
-
SJU
1 stop30h 44m
Air Canada
Fri 25/91:00 a.m.
SJU
-
YWG
2 stops16h 17m
Air Canada
Deal found 11/5C$ 697
Fri 15/56:05 p.m.
YWG
-
SJU
2 stops42h 15m
WestJet
Fri 22/52:35 p.m.
SJU
-
YWG
2 stops56h 05m
WestJet
Deal found 9/5C$ 951
Mon 8/610:45 a.m.
YWG
-
SJU
2 stops25h 19m
WestJet
Mon 15/62:14 p.m.
SJU
-
YWG
2 stops35h 41m
WestJet
Deal found 9/5C$ 963
Wed 19/87:00 a.m.
YWG
-
SJU
2 stops27h 57m
United Airlines
Sat 29/81:00 a.m.
SJU
-
YWG
2 stops22h 33m
United Airlines
Deal found 11/5C$ 969
Thu 20/87:00 a.m.
YWG
-
SJU
1 stop30h 44m
United Airlines
Sat 29/81:00 a.m.
SJU
-
YWG
2 stops22h 33m
United Airlines
Deal found 8/5C$ 971
Sat 27/68:45 a.m.
YWG
-
SJU
2 stops19h 44m
United Airlines
Thu 2/77:40 a.m.
SJU
-
YWG
2 stops16h 40m
United Airlines
Deal found 10/5C$ 996
Sat 27/64:25 p.m.
YWG
-
SJU
2 stops19h 39m
WestJet
Thu 2/77:30 a.m.
SJU
-
YWG
2 stops27h 15m
WestJet
Deal found 11/5C$ 1,041

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 13 May 2026.

Round-trip from

C$ 697

One-way from

C$ 407

Popular in

December

Cheapest in

July
Air Canada
  • Air Canada
  • 22/9-25/9
  • 3 total stops
  • 47h 01m total
  • Winnipeg to Puerto Rico
Search Deals
5/6
  • 5/6
  • 3 total stops
  • 29h 56m total
  • Winnipeg to Puerto Rico
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 163 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

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 13 May 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

Cheapest round-trip

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 22/9

7:00 a.m.-2:44 p.m.

1 stop30h 44m

San Juan Luis Munoz Marin Intl

Fri 25/9

1:00 a.m.-4:17 p.m.

2 stops16h 17m

C$ 697

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 8/6

10:45 a.m.-1:04 p.m.

2 stops25h 19m

San Juan Luis Munoz Marin Intl

Mon 15/6

2:14 p.m.-12:55 a.m.

2 stops35h 41m

C$ 963

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 19/8

7:00 a.m.-11:57 a.m.

2 stops27h 57m

San Juan Luis Munoz Marin Intl

Sat 29/8

1:00 a.m.-10:33 p.m.

2 stops22h 33m

C$ 969

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 20/8

7:00 a.m.-12:54 p.m.

2 stops28h 54m

San Juan Luis Munoz Marin Intl

Sat 29/8

1:00 a.m.-10:33 p.m.

2 stops22h 33m

C$ 971
Quickest round-trip

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 27/6

8:45 a.m.-5:29 a.m.

2 stops19h 44m

San Juan Luis Munoz Marin Intl

Thu 2/7

7:40 a.m.-11:20 p.m.

2 stops16h 40m

C$ 996
Cheapest one-way

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 5/6

9:05 p.m.-4:01 a.m.

3 stops29h 56m

C$ 407
Quickest one-way

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 5/6

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

1 stop12h 34m

C$ 484

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 25/6

10:45 a.m.-1:04 p.m.

2 stops25h 19m

C$ 574

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 25/6

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

1 stop31h 53m

C$ 575

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/5

Sorted by cheapest first

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 13 May 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
3,334 reviews
Check prices

Crew

7.9

Comfort

7.0

Entertainment

6.1

Food

6.2

Boarding

7.4

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
3,334 reviews
WestJet
7.2
Good
3,334 reviews
Check prices

Crew

7.9

Comfort

7.0

Entertainment

6.1

Food

6.2

Boarding

7.4

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.

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

    A quick flight from Winnipeg to Puerto Rico can take about 30h 44m. Air Canada provides one of the quickest options available for as low as C$ 697. The distance between Winnipeg and Puerto Rico is about 4461 km.

  • 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 13 May 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 759AverageC$ 911FlexibilityNo 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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