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Cheap flights from Winnipeg to Puerto Rico from C$ 267

YWG — SJU
15 Oct — 22 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 24/105:25 p.m. -
1 stop18h 30m
Sun 1/112:25 p.m. -
1 stop11h 19m
Deal found 12/9C$ 695
Sat 24/106:15 a.m. -
2 stops12h 15m
Sun 1/114:00 p.m. -
3 stops21h 05m
Deal found 12/9C$ 696
Sat 7/116:55 p.m. -
1 stop16h 35m
Tue 10/112:05 a.m. -
2 stops16h 33m
Deal found 13/9C$ 725
Wed 16/127:00 a.m. -
1 stop14h 52m
Thu 17/126:25 p.m. -
1 stop22h 15m
Deal found 12/9C$ 756
Fri 6/115:15 a.m. -
2 stops17h 21m
Thu 12/114:55 p.m. -
1 stop21h 28m
Deal found 14/9C$ 772
Mon 5/104:10 p.m. -
2 stops20h 35m
Sat 10/106:45 p.m. -
2 stops21h 24m
Deal found 11/9C$ 797
Sun 4/107:00 a.m. -
1 stop30h 44m
Wed 7/103:56 p.m. -
1 stop21h 41m
Deal found 12/9C$ 806

Find flight deals from Winnipeg to Puerto Rico

Round-trip from

C$ 633

One-way from

C$ 267
United Airlines
  • United Airlines
  • 6/2-13/2
  • 4 total stops
  • 28h 07m total
  • Winnipeg to Puerto Rico
Search Deals
8/11-31/12
  • 8/11-31/12
  • 2 total stops
  • 26h 24m total
  • Winnipeg to Puerto Rico
Search Deals

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

Sun 8/11

8:35 p.m.-12:59 a.m.

2 stops26h 24m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 267

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Tue 10/11

8:05 p.m.-1:25 p.m.

2 stops39h 20m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 350

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Wed 11/11

8:05 p.m.-2:50 a.m.

2 stops28h 45m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 410

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Mon 28/12

8:35 p.m.-2:07 a.m.

3 stops27h 32m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 464

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Sun 8/11

2:15 p.m.-9:00 p.m.

1 stop28h 45m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 500

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Sun 8/11

2:15 p.m.-3:40 p.m.

1 stop23h 25m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 521

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Fri 18/12

7:00 a.m.-2:43 p.m.

1 stop29h 43m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 550
Quickest round-trip

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Fri 18/12

8:30 p.m.-2:55 p.m.

2 stops16h 25m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 652

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Sat 24/10

5:25 p.m.-12:55 p.m.

1 stop18h 30m

San Juan Luis Munoz Marin Intl

Sun 1/11

2:25 p.m.-11:44 p.m.

1 stop11h 19m

C$ 695

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Mon 26/10

5:40 p.m.-12:05 p.m.

2 stops17h 25m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 781

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

Showing 1-10 of 18 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
3,443 reviews
Check prices

Boarding

7.4

Comfort

7.1

Food

6.2

Crew

7.9

Entertainment

6.1

Overall

7.2

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
3,443 reviews
WestJet
7.2
Good
3,443 reviews
Check prices

Boarding

7.4

Comfort

7.1

Food

6.2

Crew

7.9

Entertainment

6.1

Overall

7.2

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 15h 36m. Air Canada provides one of the quickest options available for as low as C$ 788. 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$ 833AverageC$ 976FlexibilityNo 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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