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Cheap flights from Winnipeg to Puerto Rico from C$ 389

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 21/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
10 Aug — 17 Aug1
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 11 July 2026.

Wed 26/87:00 a.m.
YWG
-
SJU
2 stops15h 50m
United Airlines
Sat 5/91:00 a.m.
SJU
-
YWG
2 stops11h 52m
United Airlines
Deal found 6/7C$ 600
Wed 26/87:00 a.m.
YWG
-
SJU
2 stops15h 50m
United Airlines
Tue 1/91:00 a.m.
SJU
-
YWG
2 stops11h 52m
United Airlines
Deal found 6/7C$ 665
Fri 28/82:00 p.m.
YWG
-
SJU
1 stop23h 44m
Air Canada
Fri 4/93:56 p.m.
SJU
-
YWG
1 stop31h 37m
Air Canada
Deal found 6/7C$ 685
Mon 24/84:10 p.m.
YWG
-
SJU
2 stops20h 35m
Air Canada
Fri 4/93:56 p.m.
SJU
-
YWG
1 stop20h 56m
Air Canada
Deal found 6/7C$ 689
Fri 28/82:00 p.m.
YWG
-
SJU
1 stop23h 44m
Air Canada
Tue 1/97:00 a.m.
SJU
-
YWG
2 stops17h 20m
Air Canada
Deal found 6/7C$ 696
Mon 24/84:10 p.m.
YWG
-
SJU
2 stops20h 35m
Air Canada
Tue 1/97:00 a.m.
SJU
-
YWG
2 stops17h 20m
Air Canada
Deal found 6/7C$ 701
Tue 25/85:25 p.m.
YWG
-
SJU
2 stops19h 20m
Air Canada
Tue 1/97:00 a.m.
SJU
-
YWG
2 stops17h 20m
Air Canada
Deal found 6/7C$ 706
Mon 7/95:25 p.m.
YWG
-
SJU
2 stops19h 28m
Air Canada
Thu 10/92:55 p.m.
SJU
-
YWG
2 stops21h 17m
Air Canada
Deal found 7/7C$ 708
Wed 26/87:00 a.m.
YWG
-
SJU
2 stops15h 50m
United Airlines
Tue 1/93:56 p.m.
SJU
-
YWG
1 stop20h 56m
United Airlines
Deal found 6/7C$ 749
Mon 7/92:00 p.m.
YWG
-
SJU
1 stop23h 44m
United Airlines
Fri 11/91:00 a.m.
SJU
-
YWG
2 stops11h 52m
United Airlines
Deal found 9/7C$ 752
Fri 28/87:00 a.m.
YWG
-
SJU
1 stop30h 44m
Air Canada
Wed 2/93:56 p.m.
SJU
-
YWG
1 stop31h 37m
Air Canada
Deal found 6/7C$ 774
Mon 24/84:10 p.m.
YWG
-
SJU
2 stops20h 35m
Air Canada
Wed 2/93:56 p.m.
SJU
-
YWG
1 stop31h 37m
Air Canada
Deal found 6/7C$ 778

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 11 July 2026.

Round-trip from

C$ 600

One-way from

C$ 389

Popular in

February

Cheapest in

December

Average price

C$ 1,045
United Airlines
  • United Airlines
  • 26/8-5/9
  • 4 total stops
  • 27h 42m total
  • Winnipeg to Puerto Rico
Search Deals
Air Canada
  • Air Canada
  • 21/8
  • 1 total stop
  • 23h 44m total
  • Winnipeg to Puerto Rico
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 11 July 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

Mon 7/9

5:25 p.m.-1:53 p.m.

2 stops19h 28m

San Juan Luis Munoz Marin Intl

Thu 10/9

2:55 p.m.-11:12 a.m.

2 stops21h 17m

C$ 708
Quickest round-trip

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 7/9

2:00 p.m.-1:53 p.m.

2 stops22h 53m

San Juan Luis Munoz Marin Intl

Fri 11/9

1:00 a.m.-11:52 a.m.

2 stops11h 52m

C$ 752

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 26/8

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

1 stop30h 44m

San Juan Luis Munoz Marin Intl

Thu 3/9

3:56 p.m.-10:33 p.m.

1 stop31h 37m

C$ 887

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 22/8

7:00 a.m.-11:50 p.m.

2 stops15h 50m

San Juan Luis Munoz Marin Intl

Fri 4/9

4:55 p.m.-11:52 a.m.

2 stops19h 57m

C$ 887

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 25/8

2:00 p.m.-1:45 p.m.

2 stops22h 45m

San Juan Luis Munoz Marin Intl

Fri 4/9

4:55 p.m.-11:52 a.m.

2 stops19h 57m

C$ 887

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 24/8

2:00 p.m.-1:45 p.m.

2 stops22h 45m

San Juan Luis Munoz Marin Intl

Tue 1/9

3:56 p.m.-10:33 p.m.

1 stop31h 37m

C$ 887

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 24/8

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

1 stop30h 44m

San Juan Luis Munoz Marin Intl

Mon 31/8

4:55 p.m.-11:52 a.m.

2 stops19h 57m

C$ 887

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 7/9

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

1 stop30h 44m

San Juan Luis Munoz Marin Intl

Thu 10/9

3:56 p.m.-10:33 p.m.

1 stop31h 37m

C$ 887

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 28/8

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

1 stop30h 44m

San Juan Luis Munoz Marin Intl

Mon 31/8

4:55 p.m.-11:52 a.m.

2 stops19h 57m

C$ 887
Cheapest one-way

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 21/8

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

1 stop23h 44m

C$ 389

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/7

Showing 1-10 of 14 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 11 July 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
3,407 reviews
Check prices

Food

6.2

Entertainment

6.1

Crew

7.9

Overall

7.2

Boarding

7.4

Comfort

7.0

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
3,407 reviews
WestJet
7.2
Good
3,407 reviews
Check prices

Food

6.2

Entertainment

6.1

Crew

7.9

Overall

7.2

Boarding

7.4

Comfort

7.0

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 19h 28m. Air Canada provides one of the quickest options available for as low as C$ 708. 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 11 July 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 848AverageC$ 977FlexibilityNo 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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