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Cheap flights from Winnipeg to Puerto Rico from C$ 332

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 27/5. 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
7:20 p.m. - 1:45 p.m.
YWG
-
SJU
17h 25m
2 stops
Air Canada Logo
6:45 p.m. - 11:08 a.m.
SJU
-
YWG
17h 23m
2 stops
C$ 688Air Canada
Sun, 3 May - Thu, 7 May
Air Canada Logo
7:20 p.m. - 1:45 p.m.
YWG
-
SJU
17h 25m
2 stops
Air Canada Logo
6:45 p.m. - 11:08 a.m.
SJU
-
YWG
17h 23m
2 stops
C$ 756Air Canada
Sun, 3 May - Thu, 7 May
Multiple Airlines Logo
5:10 p.m. - 10:21 p.m.
YWG
-
SJU
28h 11m
2 stops
Multiple Airlines Logo
8:04 p.m. - 12:55 a.m.
SJU
-
YWG
29h 51m
3 stops
C$ 842Multiple Airlines
Sun, 3 May - Thu, 7 May
WestJet Logo
10:45 a.m. - 11:46 a.m.
YWG
-
SJU
24h 01m
2 stops
WestJet Logo
7:30 a.m. - 12:55 a.m.
SJU
-
YWG
18h 25m
2 stops
C$ 925WestJet
Sat, 1 Aug - Sat, 8 Aug
Multiple Airlines Logo
5:10 a.m. - 12:27 a.m.
YWG
-
SJU
18h 17m
3 stops
Multiple Airlines Logo
8:04 p.m. - 12:55 a.m.
SJU
-
YWG
29h 51m
3 stops
C$ 933Multiple Airlines
Sun, 3 May - Thu, 7 May
Air Canada Logo
7:20 p.m. - 1:45 p.m.
YWG
-
SJU
17h 25m
2 stops
Air Canada Logo
3:56 p.m. - 11:52 a.m.
SJU
-
YWG
20h 56m
1 stop
C$ 944Air Canada
Sun, 3 May - Thu, 7 May
WestJet Logo
4:25 p.m. - 12:54 p.m.
YWG
-
SJU
19h 29m
2 stops
WestJet Logo
2:04 p.m. - 9:45 a.m.
SJU
-
YWG
20h 41m
2 stops
C$ 959WestJet
Sat, 27 Jun - Thu, 2 Jul
WestJet Logo
6:05 p.m. - 1:00 p.m.
YWG
-
SJU
17h 55m
2 stops
WestJet Logo
2:26 p.m. - 9:45 a.m.
SJU
-
YWG
20h 19m
2 stops
C$ 963WestJet
Fri, 18 Sep - Mon, 21 Sep
Air Canada Logo
7:20 p.m. - 1:45 p.m.
YWG
-
SJU
17h 25m
2 stops
Air Canada Logo
3:56 p.m. - 11:52 a.m.
SJU
-
YWG
20h 56m
1 stop
C$ 972Air Canada
Sun, 3 May - Thu, 7 May
WestJet Logo
6:15 a.m. - 8:43 p.m.
YWG
-
SJU
13h 28m
2 stops
WestJet Logo
2:04 p.m. - 9:45 a.m.
SJU
-
YWG
20h 41m
2 stops
C$ 997WestJet
Sat, 27 Jun - Thu, 2 Jul

WestJet flights from Winnipeg to Puerto Rico

Our best WestJet deals on Winnipeg to Puerto Rico flight tickets
WestJet
17 Apr
YWG7:30 a.m.Winnipeg
11h 54m
1 stop
SJU8:24 p.m.San Juan Luis Munoz Marin Intl
25 Apr
SJU2:03 p.m.San Juan Luis Munoz Marin Intl
20h 42m
2 stops
YWG9:45 a.m.Winnipeg
C$ 912
WestJet
1 Aug
YWG10:45 a.m.Winnipeg
24h 01m
2 stops
SJU11:46 a.m.San Juan Luis Munoz Marin Intl
8 Aug
SJU7:30 a.m.San Juan Luis Munoz Marin Intl
18h 25m
2 stops
YWG12:55 a.m.Winnipeg
C$ 925
WestJet
27 Jun
YWG4:25 p.m.Winnipeg
19h 29m
2 stops
SJU12:54 p.m.San Juan Luis Munoz Marin Intl
2 Jul
SJU2:04 p.m.San Juan Luis Munoz Marin Intl
20h 41m
2 stops
YWG9:45 a.m.Winnipeg
C$ 959

United Airlines flights from Winnipeg to Puerto Rico

Our best United Airlines deals on Winnipeg to Puerto Rico flight tickets
United Airlines
3 May
YWG8:10 a.m.Winnipeg
12h 14m
2 stops
SJU9:24 p.m.San Juan Luis Munoz Marin Intl
7 May
SJU1:40 p.m.San Juan Luis Munoz Marin Intl
32h 17m
1 stop
YWG8:57 p.m.Winnipeg
C$ 1,009
United Airlines
27 Jun
YWG7:00 a.m.Winnipeg
12h 34m
1 stop
SJU8:34 p.m.San Juan Luis Munoz Marin Intl
1 Jul
SJU1:00 a.m.San Juan Luis Munoz Marin Intl
23h 20m
2 stops
YWG11:20 p.m.Winnipeg
C$ 1,030
United Airlines
3 May
YWG8:45 a.m.Winnipeg
31h 53m
1 stop
SJU5:38 p.m.San Juan Luis Munoz Marin Intl
7 May
SJU7:40 a.m.San Juan Luis Munoz Marin Intl
29h 12m
1 stop
YWG11:52 a.m.Winnipeg
C$ 1,045

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 13 April 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

Sun 3/5

7:20 p.m.-1:45 p.m.

2 stops17h 25m

San Juan Luis Munoz Marin Intl

Thu 7/5

6:45 p.m.-11:08 a.m.

2 stops17h 23m

C$ 688

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 3/5

7:20 p.m.-1:45 p.m.

2 stops17h 25m

San Juan Luis Munoz Marin Intl

Thu 7/5

6:45 p.m.-11:08 a.m.

2 stops17h 23m

C$ 756

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 3/5

5:10 p.m.-10:21 p.m.

2 stops28h 11m

San Juan Luis Munoz Marin Intl

Thu 7/5

8:04 p.m.-12:55 a.m.

3 stops29h 51m

C$ 842

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 1/8

10:45 a.m.-11:46 a.m.

2 stops24h 01m

San Juan Luis Munoz Marin Intl

Sat 8/8

7:30 a.m.-12:55 a.m.

2 stops18h 25m

C$ 925

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 3/5

5:10 a.m.-12:27 a.m.

3 stops18h 17m

San Juan Luis Munoz Marin Intl

Thu 7/5

8:04 p.m.-12:55 a.m.

3 stops29h 51m

C$ 933

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 3/5

7:20 p.m.-1:45 p.m.

2 stops17h 25m

San Juan Luis Munoz Marin Intl

Thu 7/5

3:56 p.m.-11:52 a.m.

1 stop20h 56m

C$ 944

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 27/6

4:25 p.m.-12:54 p.m.

2 stops19h 29m

San Juan Luis Munoz Marin Intl

Thu 2/7

2:04 p.m.-9:45 a.m.

2 stops20h 41m

C$ 959

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 18/9

6:05 p.m.-1:00 p.m.

2 stops17h 55m

San Juan Luis Munoz Marin Intl

Mon 21/9

2:26 p.m.-9:45 a.m.

2 stops20h 19m

C$ 963

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 3/5

7:20 p.m.-1:45 p.m.

2 stops17h 25m

San Juan Luis Munoz Marin Intl

Thu 7/5

3:56 p.m.-11:52 a.m.

1 stop20h 56m

C$ 972
Quickest round-trip

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 27/6

6:15 a.m.-8:43 p.m.

2 stops13h 28m

San Juan Luis Munoz Marin Intl

Thu 2/7

2:04 p.m.-9:45 a.m.

2 stops20h 41m

C$ 997

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first
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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

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

14h 24m

Direct flights

None
The fastest flight from Winnipeg to Puerto Rico takes 14h 24m
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$ 766Free CancellationRating
7.2
3,320 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$ 417
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