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Cheap flights from Winnipeg to Puerto Rico from C$ 297

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 26/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
2 May — 9 May1
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 2 April 2026.

Tue 22/93:20 p.m.
YWG
-
SJU
2 stops19h 37m
Air Canada
Thu 24/91:05 a.m.
SJU
-
YWG
2 stops23h 02m
Air Canada
Deal found 31/3C$ 649
Thu 30/47:05 p.m.
YWG
-
SJU
2 stops28h 49m
Multiple Airlines
Wed 6/512:59 a.m.
SJU
-
YWG
2 stops16h 26m
Multiple Airlines
Deal found 31/3C$ 874
Tue 22/97:00 a.m.
YWG
-
SJU
2 stops15h 50m
United Airlines
Fri 25/92:00 p.m.
SJU
-
YWG
1 stop31h 48m
United Airlines
Deal found 30/3C$ 921
Sat 18/45:10 p.m.
YWG
-
SJU
1 stop18h 50m
Multiple Airlines
Sun 26/411:02 a.m.
SJU
-
YWG
2 stops52h 38m
Multiple Airlines
Deal found 1/4C$ 942
Mon 13/710:45 a.m.
YWG
-
SJU
2 stops25h 10m
WestJet
Wed 15/72:05 p.m.
SJU
-
YWG
2 stops20h 40m
WestJet
Deal found 30/3C$ 946
Sat 18/45:00 a.m.
YWG
-
SJU
2 stops30h 52m
WestJet
Sun 26/47:15 a.m.
SJU
-
YWG
2 stops35h 00m
WestJet
Deal found 1/4C$ 960

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 2 April 2026.

Round-trip from

C$ 649

One-way from

C$ 297

Popular in

December

Cheapest in

May

Average price

C$ 840
Air Canada
  • Air Canada
  • 22/9-24/9
  • 4 total stops
  • 42h 39m total
  • Winnipeg to Puerto Rico
Search Deals
26/4
  • 26/4
  • 3 total stops
  • 24h 24m total
  • Winnipeg to Puerto Rico
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 157 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 49 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 2 April 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

3:20 p.m.-11:57 a.m.

2 stops19h 37m

San Juan Luis Munoz Marin Intl

Thu 24/9

1:05 a.m.-11:07 p.m.

2 stops23h 02m

C$ 649

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 30/4

7:05 p.m.-12:54 a.m.

2 stops28h 49m

San Juan Luis Munoz Marin Intl

Wed 6/5

12:59 a.m.-4:25 p.m.

2 stops16h 26m

C$ 874

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 22/9

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

2 stops15h 50m

San Juan Luis Munoz Marin Intl

Fri 25/9

2:00 p.m.-8:48 p.m.

1 stop31h 48m

C$ 921
Quickest round-trip

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 13/7

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

1 stop12h 34m

San Juan Luis Munoz Marin Intl

Tue 14/7

1:00 a.m.-11:20 p.m.

2 stops23h 20m

C$ 990
Cheapest one-way
Quickest one-way

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 27/4

9:05 p.m.-5:59 p.m.

3 stops19h 54m

C$ 300

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 14/5

4:25 p.m.-12:01 p.m.

2 stops42h 36m

C$ 511

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 27/4

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

1 stop31h 53m

C$ 558

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 14/5

2:00 p.m.-8:34 p.m.

1 stop29h 34m

C$ 560

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 26/4

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

1 stop31h 53m

C$ 679

Flights are sorted by cheapest round-trip flights first.

Deals found on 31/3

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 2 April 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
3,309 reviews
Check prices

Crew

7.9

Food

6.2

Entertainment

6.1

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
3,309 reviews
WestJet
7.2
Good
3,309 reviews
Check prices

Crew

7.9

Food

6.2

Entertainment

6.1

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 37m. Air Canada provides one of the quickest options available for as low as C$ 649. 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

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 2 April 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 724AverageC$ 902FlexibilityNo 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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