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Cheap flights from Winnipeg to Puerto Rico from C$ 316

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 19/8. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Winnipeg to Puerto Rico

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:05 p.m. - 7:30 p.m.
YWG
-
SJU
21h 25m
3 stops
Multiple Airlines Logo
4:30 p.m. - 10:20 a.m.
SJU
-
YWG
18h 50m
3 stops
C$ 798Multiple Airlines
Fri, 4 Sep - Tue, 8 Sep
Multiple Airlines Logo
9:05 p.m. - 7:30 p.m.
YWG
-
SJU
21h 25m
3 stops
Multiple Airlines Logo
4:30 p.m. - 8:25 a.m.
SJU
-
YWG
16h 55m
2 stops
C$ 809Multiple Airlines
Fri, 4 Sep - Tue, 8 Sep
United Airlines Logo
2:00 p.m. - 1:53 p.m.
YWG
-
SJU
22h 53m
2 stops
United Airlines Logo
4:55 p.m. - 11:52 a.m.
SJU
-
YWG
19h 57m
2 stops
C$ 886United Airlines
Mon, 7 Sep - Thu, 10 Sep
United Airlines Logo
2:00 p.m. - 1:53 p.m.
YWG
-
SJU
22h 53m
2 stops
United Airlines Logo
4:55 p.m. - 11:52 a.m.
SJU
-
YWG
19h 57m
2 stops
C$ 888United Airlines
Mon, 7 Sep - Thu, 10 Sep
United Airlines Logo
2:00 p.m. - 2:44 p.m.
YWG
-
SJU
23h 44m
1 stop
United Airlines Logo
1:00 a.m. - 4:20 p.m.
SJU
-
YWG
16h 20m
2 stops
C$ 906United Airlines
Sun, 23 Aug - Mon, 24 Aug
United Airlines Logo
7:00 a.m. - 2:44 p.m.
YWG
-
SJU
30h 44m
1 stop
United Airlines Logo
4:55 p.m. - 10:33 p.m.
SJU
-
YWG
30h 38m
2 stops
C$ 908United Airlines
Mon, 7 Sep - Thu, 10 Sep
United Airlines Logo
2:00 p.m. - 1:53 p.m.
YWG
-
SJU
22h 53m
2 stops
United Airlines Logo
4:55 p.m. - 11:52 a.m.
SJU
-
YWG
19h 57m
2 stops
C$ 910United Airlines
Mon, 7 Sep - Thu, 10 Sep
United Airlines Logo
7:00 a.m. - 2:44 p.m.
YWG
-
SJU
30h 44m
1 stop
United Airlines Logo
1:25 p.m. - 11:15 a.m.
SJU
-
YWG
22h 50m
2 stops
C$ 915United Airlines
Sun, 16 Aug - Tue, 25 Aug
United Airlines Logo
7:00 a.m. - 2:44 p.m.
YWG
-
SJU
30h 44m
1 stop
United Airlines Logo
3:56 p.m. - 10:33 p.m.
SJU
-
YWG
31h 37m
1 stop
C$ 930United Airlines
Mon, 7 Sep - Thu, 10 Sep
United Airlines Logo
7:00 a.m. - 1:45 p.m.
YWG
-
SJU
29h 45m
2 stops
United Airlines Logo
1:00 a.m. - 9:30 p.m.
SJU
-
YWG
21h 30m
2 stops
C$ 950United Airlines
Sun, 23 Aug - Mon, 24 Aug

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United Airlines flights from Winnipeg to Puerto Rico

Our best United Airlines deals on Winnipeg to Puerto Rico flight tickets
United Airlines
7 Sep
YWG2:00 p.m.Winnipeg
22h 53m
2 stops
SJU1:53 p.m.San Juan Luis Munoz Marin Intl
10 Sep
SJU4:55 p.m.San Juan Luis Munoz Marin Intl
19h 57m
2 stops
YWG11:52 a.m.Winnipeg
C$ 886
United Airlines
7 Sep
YWG2:00 p.m.Winnipeg
22h 53m
2 stops
SJU1:53 p.m.San Juan Luis Munoz Marin Intl
10 Sep
SJU4:55 p.m.San Juan Luis Munoz Marin Intl
19h 57m
2 stops
YWG11:52 a.m.Winnipeg
C$ 888
United Airlines
23 Aug
YWG2:00 p.m.Winnipeg
23h 44m
1 stop
SJU2:44 p.m.San Juan Luis Munoz Marin Intl
24 Aug
SJU1:00 a.m.San Juan Luis Munoz Marin Intl
16h 20m
2 stops
YWG4:20 p.m.Winnipeg
C$ 906

WestJet flights from Winnipeg to Puerto Rico

Our best WestJet deals on Winnipeg to Puerto Rico flight tickets
WestJet
7 Aug
YWG7:45 a.m.Winnipeg
28h 31m
2 stops
SJU1:16 p.m.San Juan Luis Munoz Marin Intl
9 Aug
SJU7:00 a.m.San Juan Luis Munoz Marin Intl
35h 15m
2 stops
YWG5:15 p.m.Winnipeg
C$ 1,050
WestJet
23 Dec
YWG8:05 p.m.Winnipeg
16h 30m
2 stops
SJU2:35 p.m.San Juan Luis Munoz Marin Intl
31 Dec
SJU4:50 p.m.San Juan Luis Munoz Marin Intl
28h 25m
2 stops
YWG7:15 p.m.Winnipeg
C$ 1,273

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 15 July 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

Fri 4/9

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

3 stops21h 25m

San Juan Luis Munoz Marin Intl

Tue 8/9

4:30 p.m.-10:20 a.m.

3 stops18h 50m

C$ 798
Quickest round-trip

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 4/9

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

3 stops21h 25m

San Juan Luis Munoz Marin Intl

Tue 8/9

4:30 p.m.-8:25 a.m.

2 stops16h 55m

C$ 809

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 7/9

2:00 p.m.-1:53 p.m.

2 stops22h 53m

San Juan Luis Munoz Marin Intl

Thu 10/9

4:55 p.m.-11:52 a.m.

2 stops19h 57m

C$ 886

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 7/9

2:00 p.m.-1:53 p.m.

2 stops22h 53m

San Juan Luis Munoz Marin Intl

Thu 10/9

4:55 p.m.-11:52 a.m.

2 stops19h 57m

C$ 888

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 23/8

2:00 p.m.-2:44 p.m.

1 stop23h 44m

San Juan Luis Munoz Marin Intl

Mon 24/8

1:00 a.m.-4:20 p.m.

2 stops16h 20m

C$ 906

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 7/9

7:00 a.m.-2:44 p.m.

1 stop30h 44m

San Juan Luis Munoz Marin Intl

Thu 10/9

4:55 p.m.-10:33 p.m.

2 stops30h 38m

C$ 908

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 7/9

2:00 p.m.-1:53 p.m.

2 stops22h 53m

San Juan Luis Munoz Marin Intl

Thu 10/9

4:55 p.m.-11:52 a.m.

2 stops19h 57m

C$ 910

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 16/8

7:00 a.m.-2:44 p.m.

1 stop30h 44m

San Juan Luis Munoz Marin Intl

Tue 25/8

1:25 p.m.-11:15 a.m.

2 stops22h 50m

C$ 915

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 7/9

7:00 a.m.-2:44 p.m.

1 stop30h 44m

San Juan Luis Munoz Marin Intl

Thu 10/9

3:56 p.m.-10:33 p.m.

1 stop31h 37m

C$ 930

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 23/8

7:00 a.m.-1:45 p.m.

2 stops29h 45m

San Juan Luis Munoz Marin Intl

Mon 24/8

1:00 a.m.-9:30 p.m.

2 stops21h 30m

C$ 950

Flights are sorted by cheapest round-trip flights 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

13h 07m

Direct flights

None
The fastest flight from Winnipeg to Puerto Rico takes 13h 07m
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$ 845Free CancellationRating
7.2
3,410 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.
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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
Flights to San Juanfrom C$ 335
Flights to Aguadillafrom C$ 855