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Cheap flights from Winnipeg to Puerto Rico from C$ 339

YWG — SJU
10 Oct — 17 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

Tue 22/98:45 a.m. -
2 stops14h 05m
Sat 26/91:00 a.m. -
2 stops12h 37m
Deal found 5/9C$ 677
Sun 4/107:10 p.m. -
2 stops27h 40m
Thu 8/106:45 p.m. -
2 stops22h 42m
Deal found 6/9C$ 780
Sun 25/106:55 p.m. -
2 stops24h 05m
Sun 1/112:25 p.m. -
1 stop11h 19m
Deal found 9/9C$ 831
Sun 4/102:00 p.m. -
2 stops22h 45m
Tue 6/101:00 a.m. -
2 stops12h 37m
Deal found 9/9C$ 860
Fri 30/108:40 a.m. -
1 stop31h 45m
Sun 8/112:21 p.m. -
1 stop32h 36m
Deal found 9/9C$ 917
Fri 30/1012:10 p.m. -
2 stops23h 45m
Sun 8/1111:40 a.m. -
3 stops26h 05m
Deal found 9/9C$ 922

Find flight deals from Winnipeg to Puerto Rico

Round-trip from

C$ 677

One-way from

C$ 339

Popular in

February

Cheapest in

December

Average price

C$ 971
United Airlines
  • United Airlines
  • 22/9-26/9
  • 4 total stops
  • 26h 42m total
  • Winnipeg to Puerto Rico
Search Deals
6/10-31/12
  • 6/10-31/12
  • 3 total stops
  • 40h 31m total
  • Winnipeg to Puerto Rico
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (C$ 45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 19 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

Tue 6/10

9:05 p.m.-2:36 p.m.

3 stops40h 31m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 339

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Sun 27/9

6:05 p.m.-3:17 p.m.

2 stops44h 12m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 370
Quickest round-trip

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

Wed 31/12

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

Nonstop0h 00m

C$ 398

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Sun 27/9

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$ 594

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Mon 28/9

2:00 p.m.-11:50 p.m.

2 stops32h 50m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 594

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Fri 30/10

6:55 p.m.-12:55 p.m.

1 stop17h 00m

San Juan Luis Munoz Marin Intl

Sun 8/11

11:40 a.m.-1:00 p.m.

3 stops27h 20m

C$ 902

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Wed 23/9

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

1 stop31h 53m

San Juan Luis Munoz Marin Intl

Sat 26/9

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

2 stops12h 37m

C$ 906

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Fri 30/10

8:40 a.m.-5:25 p.m.

1 stop31h 45m

San Juan Luis Munoz Marin Intl

Sun 8/11

2:21 p.m.-8:57 p.m.

1 stop32h 36m

C$ 917

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Sat 19/12

5:00 a.m.-2:05 p.m.

1 stop31h 05m

San Juan Luis Munoz Marin Intl

Sat 2/1

3:00 p.m.-12:44 a.m.

1 stop11h 44m

C$ 931

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Sun 4/10

8:45 a.m.-11:57 a.m.

2 stops26h 12m

San Juan Luis Munoz Marin Intl

Thu 8/10

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

1 stop31h 57m

C$ 953

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/9

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
3,446 reviews
Check prices

Entertainment

6.1

Food

6.2

Overall

7.2

Crew

7.9

Comfort

7.1

Boarding

7.4

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
3,446 reviews
WestJet
7.2
Good
3,446 reviews
Check prices

Entertainment

6.1

Food

6.2

Overall

7.2

Crew

7.9

Comfort

7.1

Boarding

7.4

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 31h 53m. United Airlines provides one of the quickest options available for as low as C$ 906. 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

Top airline flying from Winnipeg to Puerto Rico

AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 826AverageC$ 969FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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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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