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Cheap flights from Winnipeg to Puerto Rico from C$ 293

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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
29 Apr — 6 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 30 March 2026.

Tue 22/95:10 a.m.
YWG
-
SJU
2 stops17h 40m
Air Canada
Thu 24/91:05 a.m.
SJU
-
YWG
2 stops23h 02m
Air Canada
Deal found 29/3C$ 650
Sat 25/45:00 a.m.
YWG
-
SJU
2 stops13h 22m
Multiple Airlines
Sat 2/512:57 p.m.
SJU
-
YWG
3 stops27h 22m
Multiple Airlines
Deal found 28/3C$ 734
Sat 5/127:20 p.m.
YWG
-
SJU
1 stop17h 20m
Air Canada
Fri 11/122:05 a.m.
SJU
-
YWG
2 stops13h 39m
Air Canada
Deal found 25/3C$ 788
Wed 22/47:05 p.m.
YWG
-
SJU
2 stops23h 09m
Multiple Airlines
Wed 29/412:57 p.m.
SJU
-
YWG
2 stops21h 56m
Multiple Airlines
Deal found 26/3C$ 803

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 30 March 2026.

Round-trip from

C$ 650

One-way from

C$ 293

Popular in

December

Cheapest in

May

Average price

C$ 922
Air Canada
  • Air Canada
  • 22/9-24/9
  • 4 total stops
  • 40h 42m total
  • Winnipeg to Puerto Rico
Search Deals
10/5
  • 10/5
  • 3 total stops
  • 19h 11m 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 March 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 30 March 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

Sat 25/4

5:00 a.m.-9:19 a.m.

3 stops27h 19m

San Juan Luis Munoz Marin Intl

Fri 1/5

3:21 a.m.-10:09 a.m.

3 stops31h 48m

C$ 789

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 22/4

7:05 p.m.-7:14 p.m.

2 stops23h 09m

San Juan Luis Munoz Marin Intl

Wed 29/4

12:57 p.m.-9:53 a.m.

2 stops21h 56m

C$ 803

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 22/4

7:30 a.m.-4:23 p.m.

1 stop7h 53m

San Juan Luis Munoz Marin Intl

Wed 29/4

2:45 p.m.-12:55 a.m.

2 stops35h 10m

C$ 884

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$ 890

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 22/4

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

1 stop29h 34m

San Juan Luis Munoz Marin Intl

Tue 28/4

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

2 stops11h 52m

C$ 897
Quickest round-trip

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 13/7

5:10 a.m.-8:34 p.m.

2 stops14h 24m

San Juan Luis Munoz Marin Intl

Wed 15/7

1:25 p.m.-11:15 a.m.

2 stops22h 50m

C$ 968
Cheapest one-way

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 10/5

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

1 stop29h 34m

C$ 364

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

Thu 14/5

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

1 stop29h 34m

C$ 560
Quickest one-way

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 12/5

2:00 p.m.-5:38 p.m.

3 stops26h 38m

C$ 800

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/3

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 30 March 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
3,306 reviews
Check prices

Overall

7.2

Entertainment

6.1

Boarding

7.4

Comfort

7.0

Food

6.2

Crew

7.9

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
3,306 reviews
WestJet
7.2
Good
3,306 reviews
Check prices

Overall

7.2

Entertainment

6.1

Boarding

7.4

Comfort

7.0

Food

6.2

Crew

7.9

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 7h 53m. WestJet provides one of the quickest options available for as low as C$ 884. 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 30 March 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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