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Cheap flights from Winnipeg to Puerto Rico from C$ 342

YWG — SJU
24 Oct — 31 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

Sat 24/102:00 p.m. -
1 stop29h 00m
Wed 28/107:25 a.m. -
1 stop29h 58m
Deal found 23/9C$ 717
Tue 6/108:45 a.m. -
2 stops14h 05m
Fri 9/101:00 a.m. -
2 stops12h 37m
Deal found 19/9C$ 721
Fri 23/109:05 p.m. -
3 stops27h 48m
Fri 30/104:36 p.m. -
3 stops33h 34m
Deal found 23/9C$ 724

Find flight deals from Winnipeg to Puerto Rico

Round-trip from

C$ 717

One-way from

C$ 342

Popular in

February

Cheapest in

September

Average price

C$ 689
Air Canada
  • Air Canada
  • 24/10-28/10
  • 2 total stops
  • 58h 58m total
  • Winnipeg to Puerto Rico
Search Deals
5/10-31/12
  • 5/10-31/12
  • 2 total stops
  • 30h 32m total
  • Winnipeg to Puerto Rico
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 89 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 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

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Mon 5/10

7:45 a.m.-3:17 p.m.

2 stops30h 32m

San Juan Luis Munoz Marin Intl

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 342
Quickest round-trip

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Wed 16/12

7:00 a.m.-2:13 a.m.

2 stops17h 13m

San Juan Luis Munoz Marin Intl

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 492

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Mon 30/11

8:40 a.m.-6:25 p.m.

1 stop31h 45m

San Juan Luis Munoz Marin Intl

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 514

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Mon 5/10

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

1 stop31h 53m

San Juan Luis Munoz Marin Intl

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 604

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Tue 6/10

8:45 a.m.-11:50 p.m.

2 stops14h 05m

San Juan Luis Munoz Marin Intl

Fri 9/10

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

2 stops12h 37m

C$ 721

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Fri 23/10

7:10 p.m.-8:38 p.m.

2 stops24h 28m

San Juan Luis Munoz Marin Intl

Fri 30/10

2:20 p.m.-10:05 a.m.

2 stops20h 45m

C$ 744

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Fri 8/1

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

2 stops26h 00m

San Juan Luis Munoz Marin Intl

Thu 14/1

3:48 p.m.-2:40 p.m.

1 stop24h 52m

C$ 779

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Fri 23/10

7:00 a.m.-9:18 a.m.

3 stops25h 18m

San Juan Luis Munoz Marin Intl

Fri 30/10

2:20 p.m.-4:38 p.m.

2 stops27h 18m

C$ 795

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Mon 5/10

9:25 a.m.-2:13 a.m.

2 stops15h 48m

San Juan Luis Munoz Marin Intl

Wed 7/10

8:45 a.m.-7:55 p.m.

2 stops12h 10m

C$ 893

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Fri 23/10

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

1 stop31h 53m

San Juan Luis Munoz Marin Intl

Fri 30/10

1:21 p.m.-8:57 p.m.

1 stop32h 36m

C$ 923

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/9

Showing 1-10 of 13 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

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
3,448 reviews
Check prices

Entertainment

6.1

Comfort

7.1

Overall

7.2

Boarding

7.4

Crew

7.9

Food

6.2

Reviews

1 / 20
8.0
Excellent

Seth,Sep 2026

YVR - YYC

The people from check-in, to the cabin crew, to flight crew were all pleasant and efficient. The under seat space were a little cramped.
WestJet
7.2
Good
3,448 reviews
WestJet
7.2
Good
3,448 reviews
Check prices

Entertainment

6.1

Comfort

7.1

Overall

7.2

Boarding

7.4

Crew

7.9

Food

6.2

Reviews

1 / 20
8.0
Excellent

Seth,Sep 2026

YVR - YYC

The people from check-in, to the cabin crew, to flight crew were all pleasant and efficient. The under seat space were a little cramped.

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 14h 05m. United Airlines provides one of the quickest options available for as low as C$ 721. 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$ 845AverageC$ 990FlexibilityNo 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.

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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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