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Cheap flights from Winnipeg to Puerto Rico from C$ 426

YWG — SJU
26 Sep — 3 Oct1
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

Sun 4/107:00 a.m. -
1 stop30h 44m
Wed 7/101:00 a.m. -
2 stops23h 47m
Deal found 23/8C$ 722
Sun 11/107:10 p.m. -
2 stops19h 56m
Sat 17/103:00 a.m. -
3 stops39h 25m
Deal found 27/8C$ 745
Sun 11/108:45 a.m. -
1 stop31h 53m
Sat 17/101:00 a.m. -
2 stops12h 37m
Deal found 27/8C$ 897
Sun 4/102:00 p.m. -
1 stop23h 44m
Thu 8/102:00 p.m. -
1 stop31h 57m
Deal found 26/8C$ 906

Find flight deals from Winnipeg to Puerto Rico

Round-trip from

C$ 722

One-way from

C$ 426

Popular in

February

Cheapest in

December

Average price

C$ 980
Air Canada
  • Air Canada
  • 4/10-7/10
  • 3 total stops
  • 54h 31m total
  • Winnipeg to Puerto Rico
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8/10
  • 8/10
  • 2 total stops
  • 28h 46m total
  • Winnipeg to Puerto Rico
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (C$ 41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
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Cheapflights Fare Finder

 
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
Quickest round-trip

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Sun 4/10

5:25 p.m.-1:45 p.m.

2 stops19h 20m

San Juan Luis Munoz Marin Intl

Thu 8/10

6:45 p.m.-11:12 a.m.

2 stops17h 27m

C$ 851

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Sun 11/10

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

1 stop31h 53m

San Juan Luis Munoz Marin Intl

Sat 17/10

1:00 a.m.-12:37 p.m.

2 stops12h 37m

C$ 897

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Sun 4/10

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

1 stop23h 44m

San Juan Luis Munoz Marin Intl

Thu 8/10

2:00 p.m.-8:57 p.m.

1 stop31h 57m

C$ 906

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Tue 10/11

2:15 p.m.-11:50 a.m.

2 stops19h 35m

San Juan Luis Munoz Marin Intl

Sat 14/11

2:05 a.m.-11:44 p.m.

2 stops23h 39m

C$ 951
Cheapest one-way
Quickest one-way

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Thu 8/10

7:45 a.m.-1:31 p.m.

2 stops28h 46m

C$ 426

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Sat 10/10

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

1 stop31h 53m

C$ 501

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Thu 8/10

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

1 stop31h 53m

C$ 503

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/8

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

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

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
3,438 reviews
Check prices

Boarding

7.4

Entertainment

6.1

Food

6.2

Comfort

7.1

Crew

7.9

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2026

YHZ - DTW

Better snacks I also flew Delta much better with movies and entertainment
WestJet
7.2
Good
3,438 reviews
WestJet
7.2
Good
3,438 reviews
Check prices

Boarding

7.4

Entertainment

6.1

Food

6.2

Comfort

7.1

Crew

7.9

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2026

YHZ - DTW

Better snacks I also flew Delta much better with movies and entertainment

Related info for your journey

  • 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 20m. Air Canada provides one of the quickest options available for as low as C$ 851. 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

Top airline flying from Winnipeg to Puerto Rico

AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 831AverageC$ 974FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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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.

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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.

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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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