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Cheap flights from Winnipeg to Puerto Rico from C$ 340

YWG — SJU
9 Dec — 16 Dec1
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

Mon 7/124:05 p.m. -
2 stops18h 45m
Thu 10/128:25 a.m. -
1 stop29h 58m
Deal found 4/11C$ 757
Mon 7/129:40 a.m. -
1 stop31h 45m
Thu 10/128:25 a.m. -
1 stop29h 58m
Deal found 7/11C$ 968
Sun 6/1211:00 a.m. -
2 stops23h 50m
Sun 13/123:00 p.m. -
1 stop22h 05m
Deal found 7/11C$ 1,006
Sun 6/123:15 p.m. -
2 stops19h 35m
Sun 13/125:50 p.m. -
2 stops29h 05m
Deal found 7/11C$ 1,016

Find flight deals from Winnipeg to Puerto Rico

Round-trip from

C$ 629

One-way from

C$ 340

Popular in

November

Cheapest in

September

Average price

C$ 1,821
United Airlines
  • United Airlines
  • 13/1-23/1
  • 4 total stops
  • 25h 45m total
  • Winnipeg to Puerto Rico
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United Airlines
  • United Airlines
  • 31/1-31/12
  • 2 total stops
  • 14h 57m total
  • Winnipeg to Puerto Rico
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Highest demand for flights based on searches. 17% potential increase in price (C$ 321 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease (C$ 121 potential savings vs. average RT price).
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Average for round-trip flights in November 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

WinnipegAguadilla

YWG Winnipeg - BQN Aguadilla Borinquen

YWGBQN

Winnipeg

Sun 31/1

8:00 a.m.-11:57 p.m.

2 stops14h 57m

Aguadilla Borinquen

Wed 31/12

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

Nonstop0h 00m

C$ 340

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Wed 24/3

7:00 a.m.-9:22 p.m.

2 stops13h 22m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 418

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Mon 21/12

9:40 a.m.-5:21 a.m.

1 stop18h 41m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 438

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Mon 1/2

8:00 a.m.-12:36 a.m.

2 stops15h 36m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 493
Quickest round-trip

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Sun 31/1

8:00 a.m.-9:00 p.m.

1 stop12h 00m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 533

WinnipegAguadilla

YWG Winnipeg - BQN Aguadilla Borinquen

YWGBQN

Winnipeg

Sat 13/2

9:40 a.m.-11:57 p.m.

2 stops37h 17m

Aguadilla Borinquen

Wed 31/12

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

Nonstop0h 00m

C$ 533

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Mon 21/12

7:00 a.m.-2:49 a.m.

2 stops18h 49m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 534

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Wed 17/2

8:00 a.m.-10:22 p.m.

2 stops13h 22m

San Juan Luis Munoz Marin Intl

Wed 3/3

8:05 a.m.-7:26 p.m.

2 stops12h 21m

C$ 654

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Thu 14/1

8:00 a.m.-12:36 a.m.

2 stops15h 36m

San Juan Luis Munoz Marin Intl

Sat 23/1

8:05 a.m.-7:28 p.m.

2 stops12h 23m

C$ 654

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Fri 12/2

9:40 a.m.-1:15 p.m.

2 stops26h 35m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 674

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/11

Showing 1-10 of 18 resultsSorted by cheapest first
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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.

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 13h 22m. United Airlines provides one of the quickest options available for as low as C$ 629. 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

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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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