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Cheap flights from Winnipeg to Puerto Rico from C$ 482

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Puerto Rico departing on 11/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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Find the cheapest flights from Winnipeg to Puerto Rico

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
12:20 p.m. - 11:57 a.m.
YWG
-
SJU
22h 37m
2 stops
Air Canada Logo
3:56 p.m. - 11:39 a.m.
SJU
-
YWG
20h 43m
1 stop
C$ 697Air Canada
Sat, 26 Sep - Wed, 30 Sep
Air Canada Logo
12:20 p.m. - 11:57 a.m.
YWG
-
SJU
22h 37m
2 stops
Air Canada Logo
3:56 p.m. - 11:39 a.m.
SJU
-
YWG
20h 43m
1 stop
C$ 698Air Canada
Sat, 26 Sep - Wed, 30 Sep
United Airlines Logo
7:00 a.m. - 11:50 p.m.
YWG
-
SJU
15h 50m
2 stops
United Airlines Logo
1:00 a.m. - 11:39 a.m.
SJU
-
YWG
11h 39m
2 stops
C$ 704United Airlines
Sat, 26 Sep - Tue, 29 Sep
Air Canada Logo
7:10 p.m. - 1:45 p.m.
YWG
-
SJU
17h 35m
2 stops
Air Canada Logo
6:45 p.m. - 11:12 a.m.
SJU
-
YWG
17h 27m
2 stops
C$ 709Air Canada
Sat, 26 Sep - Wed, 30 Sep
Air Canada Logo
5:10 a.m. - 11:50 p.m.
YWG
-
SJU
17h 40m
2 stops
Air Canada Logo
1:00 a.m. - 4:17 p.m.
SJU
-
YWG
16h 17m
2 stops
C$ 752Air Canada
Tue, 20 Oct - Thu, 22 Oct
United Airlines Logo
7:00 a.m. - 11:50 p.m.
YWG
-
SJU
15h 50m
2 stops
United Airlines Logo
1:00 a.m. - 11:39 a.m.
SJU
-
YWG
11h 39m
2 stops
C$ 756United Airlines
Sat, 26 Sep - Tue, 29 Sep
United Airlines Logo
7:00 a.m. - 11:50 p.m.
YWG
-
SJU
15h 50m
2 stops
United Airlines Logo
2:00 p.m. - 8:48 p.m.
SJU
-
YWG
31h 48m
1 stop
C$ 879United Airlines
Tue, 20 Oct - Fri, 23 Oct
United Airlines Logo
8:30 a.m. - 5:38 p.m.
YWG
-
SJU
32h 08m
1 stop
United Airlines Logo
3:56 p.m. - 11:39 a.m.
SJU
-
YWG
20h 43m
1 stop
C$ 881United Airlines
Sat, 26 Sep - Wed, 30 Sep
United Airlines Logo
8:30 a.m. - 5:38 p.m.
YWG
-
SJU
32h 08m
1 stop
United Airlines Logo
2:00 p.m. - 8:48 p.m.
SJU
-
YWG
31h 48m
1 stop
C$ 915United Airlines
Tue, 20 Oct - Fri, 23 Oct
United Airlines Logo
8:45 a.m. - 5:29 a.m.
YWG
-
SJU
19h 44m
2 stops
United Airlines Logo
1:00 a.m. - 11:20 p.m.
SJU
-
YWG
23h 20m
2 stops
C$ 950United Airlines
Mon, 15 Jun - Fri, 19 Jun

Air Canada flights from Winnipeg to Puerto Rico

Our best Air Canada deals on Winnipeg to Puerto Rico flight tickets
Air Canada
26 Sep
YWG12:20 p.m.Winnipeg
22h 37m
2 stops
SJU11:57 a.m.San Juan Luis Munoz Marin Intl
30 Sep
SJU3:56 p.m.San Juan Luis Munoz Marin Intl
20h 43m
1 stop
YWG11:39 a.m.Winnipeg
C$ 697
Air Canada
26 Sep
YWG12:20 p.m.Winnipeg
22h 37m
2 stops
SJU11:57 a.m.San Juan Luis Munoz Marin Intl
30 Sep
SJU3:56 p.m.San Juan Luis Munoz Marin Intl
20h 43m
1 stop
YWG11:39 a.m.Winnipeg
C$ 698
Air Canada
26 Sep
YWG7:10 p.m.Winnipeg
17h 35m
2 stops
SJU1:45 p.m.San Juan Luis Munoz Marin Intl
30 Sep
SJU6:45 p.m.San Juan Luis Munoz Marin Intl
17h 27m
2 stops
YWG11:12 a.m.Winnipeg
C$ 709

United Airlines flights from Winnipeg to Puerto Rico

Our best United Airlines deals on Winnipeg to Puerto Rico flight tickets
United Airlines
26 Sep
YWG7:00 a.m.Winnipeg
15h 50m
2 stops
SJU11:50 p.m.San Juan Luis Munoz Marin Intl
29 Sep
SJU1:00 a.m.San Juan Luis Munoz Marin Intl
11h 39m
2 stops
YWG11:39 a.m.Winnipeg
C$ 704
United Airlines
26 Sep
YWG7:00 a.m.Winnipeg
15h 50m
2 stops
SJU11:50 p.m.San Juan Luis Munoz Marin Intl
29 Sep
SJU1:00 a.m.San Juan Luis Munoz Marin Intl
11h 39m
2 stops
YWG11:39 a.m.Winnipeg
C$ 756
United Airlines
20 Oct
YWG7:00 a.m.Winnipeg
15h 50m
2 stops
SJU11:50 p.m.San Juan Luis Munoz Marin Intl
23 Oct
SJU2:00 p.m.San Juan Luis Munoz Marin Intl
31h 48m
1 stop
YWG8:48 p.m.Winnipeg
C$ 879

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Puerto Rico that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 28 May 2026.
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 - SJU

YWGSJU

Winnipeg

Sat 26/9

12:20 p.m.-11:57 a.m.

2 stops22h 37m

San Juan Luis Munoz Marin Intl

Wed 30/9

3:56 p.m.-11:39 a.m.

1 stop20h 43m

C$ 697

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 26/9

12:20 p.m.-11:57 a.m.

2 stops22h 37m

San Juan Luis Munoz Marin Intl

Wed 30/9

3:56 p.m.-11:39 a.m.

1 stop20h 43m

C$ 698
Quickest round-trip

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 26/9

7:00 a.m.-11:50 p.m.

2 stops15h 50m

San Juan Luis Munoz Marin Intl

Tue 29/9

1:00 a.m.-11:39 a.m.

2 stops11h 39m

C$ 704

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 26/9

7:10 p.m.-1:45 p.m.

2 stops17h 35m

San Juan Luis Munoz Marin Intl

Wed 30/9

6:45 p.m.-11:12 a.m.

2 stops17h 27m

C$ 709

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 20/10

5:10 a.m.-11:50 p.m.

2 stops17h 40m

San Juan Luis Munoz Marin Intl

Thu 22/10

1:00 a.m.-4:17 p.m.

2 stops16h 17m

C$ 752

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 26/9

7:00 a.m.-11:50 p.m.

2 stops15h 50m

San Juan Luis Munoz Marin Intl

Tue 29/9

1:00 a.m.-11:39 a.m.

2 stops11h 39m

C$ 756

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 20/10

7:00 a.m.-11:50 p.m.

2 stops15h 50m

San Juan Luis Munoz Marin Intl

Fri 23/10

2:00 p.m.-8:48 p.m.

1 stop31h 48m

C$ 879

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 26/9

8:30 a.m.-5:38 p.m.

1 stop32h 08m

San Juan Luis Munoz Marin Intl

Wed 30/9

3:56 p.m.-11:39 a.m.

1 stop20h 43m

C$ 881

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 20/10

8:30 a.m.-5:38 p.m.

1 stop32h 08m

San Juan Luis Munoz Marin Intl

Fri 23/10

2:00 p.m.-8:48 p.m.

1 stop31h 48m

C$ 915

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 15/6

8:45 a.m.-5:29 a.m.

2 stops19h 44m

San Juan Luis Munoz Marin Intl

Fri 19/6

1:00 a.m.-11:20 p.m.

2 stops23h 20m

C$ 950

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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See travel insights to Puerto Rico from

How to get the cheapest flight ticket from Winnipeg to Puerto Rico

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Puerto Rico?

If you aren’t able to travel to Puerto Rico during the month of October, then flying in May is also cheap. Prices for this month can be found on momondo for an average of C$ 0.

Can stopping save me money on Winnipeg to Puerto Rico flights?

You could potentially save up to 19% on your flight if you consider stops on a Winnipeg to Puerto Rico flight.

Cheap Winnipeg to Puerto Rico flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Puerto Rico

Fastest flight time

15h 50m

Direct flights

None
The fastest flight from Winnipeg to Puerto Rico takes 15h 50m
There are no direct flights from Winnipeg to Puerto Rico. There are no popular flight routes from Winnipeg to Puerto Rico.
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Frequently asked questions about flying from Winnipeg to Puerto Rico

  • When did momondo last update prices for flights from Winnipeg Airport to Puerto Rico?

    Prices for flights from Winnipeg Airport to Puerto Rico are refreshed on a daily basis.

  • How many operators does momondo search for flights from Winnipeg Airport to Puerto Rico?

  • How old do you have to be to fly from Winnipeg Airport to Puerto Rico?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Winnipeg Airport to Puerto Rico.

  • What documentation or ID do you need to fly to Puerto Rico?

    The necessary travel and health documents for your Puerto Rico trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Winnipeg to Puerto Rico

Compare and see reviews for airlines that fly from Winnipeg to Puerto Rico with momondo
Airline
Rating
Free Cancellation
Price
WestJetPriceFrom C$ 780Free CancellationRating
7.2
3,347 reviews
Search WestJet flights

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Puerto Rico?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Winnipeg to Puerto Rico . Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Winnipeg to Puerto Rico with flexible booking policies on momondo?

All flight searches from Winnipeg to Puerto Rico on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Winnipeg to Puerto Rico?

Once all potential Winnipeg to Puerto Rico flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Winnipeg to Puerto Rico right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Puerto Rico, momondo offers a useful price alert feature which will track prices for flights to Puerto Rico from Winnipeg and alert you when they change.

An easier way to manage your Puerto Rico trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
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Find better results for your trip to Puerto Rico

Popular Cities in Puerto Rico

Popular flights according to clicks in the last 7 days on momondo
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