Find flights
When to book
FAQs

Cheap flights from Winnipeg to Puerto Rico from C$ 327

YWG — SJU
5 Dec — 12 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 7/129:35 p.m. -
3 stops22h 02m
Wed 9/125:01 a.m. -
2 stops21h 09m
Deal found 3/11C$ 591
Wed 2/129:35 p.m. -
2 stops26h 32m
Wed 9/125:01 a.m. -
2 stops21h 09m
Deal found 3/11C$ 616
Mon 7/124:05 p.m. -
2 stops18h 45m
Thu 10/128:25 a.m. -
1 stop29h 58m
Deal found 3/11C$ 747
Tue 1/126:15 a.m. -
2 stops17h 21m
Tue 8/128:25 a.m. -
1 stop29h 58m
Deal found 3/11C$ 792
Mon 7/129:40 a.m. -
1 stop31h 45m
Tue 8/122:05 a.m. -
2 stops12h 18m
Deal found 31/10C$ 793
Tue 1/126:15 a.m. -
2 stops17h 21m
Mon 7/127:40 a.m. -
2 stops18h 04m
Deal found 3/11C$ 803

Find flight deals from Winnipeg to Puerto Rico

Round-trip from

C$ 591

One-way from

C$ 327

Popular in

November

Cheapest in

September

Average price

C$ 1,800
7/12-9/12
  • 7/12-9/12
  • 5 total stops
  • 43h 11m total
  • Winnipeg to Puerto Rico
Search Deals
16/11-31/12
  • 16/11-31/12
  • 2 total stops
  • 26h 24m total
  • Winnipeg to Puerto Rico
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 313 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (C$ 120 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2026
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

Mon 16/11

9:35 p.m.-1:59 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$ 327

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Tue 16/2

8:00 a.m.-11:22 p.m.

2 stops13h 22m

San Juan Luis Munoz Marin Intl

Wed 3/3

8:25 a.m.-6:26 p.m.

1 stop12h 01m

C$ 666

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Thu 17/12

9:40 a.m.-6:21 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$ 712

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Sat 26/12

1:10 p.m.-1:17 a.m.

3 stops58h 07m

San Juan Luis Munoz Marin Intl

Wed 31/12

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

Nonstop0h 00m

C$ 793

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Mon 7/12

9:40 a.m.-5:36 p.m.

2 stops29h 56m

San Juan Luis Munoz Marin Intl

Tue 8/12

2:05 a.m.-12:23 p.m.

2 stops12h 18m

C$ 793

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Fri 4/12

3:15 p.m.-10:00 p.m.

1 stop28h 45m

San Juan Luis Munoz Marin Intl

Thu 10/12

2:05 a.m.-12:23 p.m.

2 stops12h 18m

C$ 824

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Thu 14/1

9:40 a.m.-1:36 a.m.

2 stops13h 56m

San Juan Luis Munoz Marin Intl

Sat 23/1

4:55 p.m.-6:28 p.m.

1 stop27h 33m

C$ 824

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Mon 30/11

9:40 a.m.-5:36 p.m.

2 stops29h 56m

San Juan Luis Munoz Marin Intl

Mon 7/12

2:05 a.m.-12:23 p.m.

2 stops12h 18m

C$ 869

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Wed 2/12

9:40 a.m.-7:25 p.m.

1 stop31h 45m

San Juan Luis Munoz Marin Intl

Wed 9/12

7:40 a.m.-8:55 p.m.

2 stops15h 15m

C$ 903

WinnipegSan Juan

YWG Winnipeg - SJU San Juan Luis Munoz Marin Intl

YWGSJU

Winnipeg

Mon 16/11

3:15 p.m.-4:40 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$ 908

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

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.

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$ 666. 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

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.