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Cheap flights from Winnipeg to Puerto Rico from C$ 386

YWG — SJU
29 Oct — 5 Nov1
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 24/105:00 a.m. -
2 stops17h 50m
Wed 28/107:25 a.m. -
1 stop29h 58m
Deal found 24/9C$ 732
Fri 23/109:05 p.m. -
3 stops21h 25m
Thu 29/102:55 a.m. -
2 stops16h 15m
Deal found 29/9C$ 819
Fri 23/107:10 p.m. -
2 stops27h 40m
Fri 30/102:20 p.m. -
2 stops27h 18m
Deal found 29/9C$ 831
Sat 3/108:45 a.m. -
2 stops14h 05m
Sat 10/101:00 a.m. -
2 stops12h 37m
Deal found 25/9C$ 909
Tue 10/112:15 p.m. -
2 stops19h 35m
Sat 14/112:05 a.m. -
2 stops23h 39m
Deal found 25/9C$ 977

Find flight deals from Winnipeg to Puerto Rico

Round-trip from

C$ 732

One-way from

C$ 386

Popular in

February

Cheapest in

September

Average price

C$ 694
Air Canada
  • Air Canada
  • 24/10-28/10
  • 3 total stops
  • 47h 48m total
  • Winnipeg to Puerto Rico
Search Deals
13/11-31/12
  • 13/11-31/12
  • 2 total stops
  • 22h 05m total
  • Winnipeg to Puerto Rico
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 91 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 26 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
Quickest round-trip

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Fri 13/11

7:55 p.m.-8:00 p.m.

2 stops22h 05m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 386

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Fri 13/11

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$ 484

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Fri 23/10

9:05 p.m.-7:30 p.m.

3 stops21h 25m

San Juan Luis Munoz Marin Intl

Thu 29/10

2:55 a.m.-6:10 p.m.

2 stops16h 15m

C$ 819

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$ 1,007

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Fri 5/2

7:00 a.m.-1:15 p.m.

2 stops28h 15m

San Juan Luis Munoz Marin Intl

Sat 13/2

2:05 a.m.-6:41 p.m.

2 stops18h 36m

C$ 1,009

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Wed 16/12

7:15 a.m.-12:36 a.m.

2 stops15h 21m

San Juan Luis Munoz Marin Intl

Thu 17/12

4:55 p.m.-12:52 p.m.

1 stop21h 57m

C$ 1,088

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/9

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
3,449 reviews
Check prices

Boarding

7.4

Entertainment

6.1

Comfort

7.1

Overall

7.2

Food

6.2

Crew

7.9

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
3,449 reviews
WestJet
7.2
Good
3,449 reviews
Check prices

Boarding

7.4

Entertainment

6.1

Comfort

7.1

Overall

7.2

Food

6.2

Crew

7.9

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 19h 35m. United Airlines provides one of the quickest options available for as low as C$ 1,007. 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$ 850AverageC$ 997FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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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