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Cheap flights from Winnipeg to Puerto Rico from C$ 528

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 3/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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.
Multiple Airlines Logo
8:00 a.m. - 12:24 a.m.YWG-SJU
14h 24m1 stop
Multiple Airlines Logo
7:20 a.m. - 5:26 p.m.SJU-YWG
12h 06m1 stop
C$ 666Multiple Airlines
Find Deal
Tue, 25 Nov - Tue, 2 Dec
Multiple Airlines Logo
8:00 a.m. - 12:24 a.m.YWG-SJU
14h 24m1 stop
Multiple Airlines Logo
4:48 p.m. - 3:07 p.m.SJU-YWG
24h 19m2 stops
C$ 671Multiple Airlines
Find Deal
Tue, 25 Nov - Tue, 2 Dec
WestJet Logo
5:00 a.m. - 11:49 p.m.YWG-SJU
16h 49m2 stops
WestJet Logo
7:30 a.m. - 3:09 p.m.SJU-YWG
9h 39m1 stop
C$ 908WestJet
Find Deal
Tue, 3 Mar - Wed, 4 Mar
WestJet Logo
5:00 a.m. - 11:49 p.m.YWG-SJU
16h 49m2 stops
WestJet Logo
7:30 a.m. - 3:09 p.m.SJU-YWG
9h 39m1 stop
C$ 910WestJet
Find Deal
Tue, 3 Mar - Wed, 4 Mar
United Airlines Logo
7:15 a.m. - 10:22 p.m.YWG-SJU
13h 07m2 stops
United Airlines Logo
2:05 a.m. - 12:39 p.m.SJU-YWG
12h 34m2 stops
C$ 1,107United Airlines
Find Deal
Tue, 3 Mar - Tue, 3 Mar
United Airlines Logo
2:20 p.m. - 10:22 p.m.YWG-SJU
30h 02m2 stops
United Airlines Logo
2:05 a.m. - 5:19 p.m.SJU-YWG
17h 14m2 stops
C$ 1,139United Airlines
Find Deal
Tue, 25 Nov - Mon, 1 Dec
Air Canada Logo
7:05 p.m. - 2:40 p.m.YWG-SJU
17h 35m1 stop
Air Canada Logo
2:05 a.m. - 4:35 p.m.SJU-YWG
16h 30m2 stops
C$ 2,000Air Canada
Find Deal
Sat, 27 Dec - Fri, 2 Jan
Air Canada Logo
7:05 p.m. - 2:40 p.m.YWG-SJU
17h 35m1 stop
Air Canada Logo
2:05 a.m. - 4:35 p.m.SJU-YWG
16h 30m2 stops
C$ 2,002Air Canada
Find Deal
Sat, 27 Dec - Fri, 2 Jan
American Airlines Logo
12:10 p.m. - 9:36 a.m.YWG-SJU
19h 26m3 stops
American Airlines Logo
5:24 a.m. - 11:35 p.m.SJU-YWG
20h 11m3 stops
C$ 2,451American Airlines
Find Deal
Sat, 27 Dec - Sat, 3 Jan
American Airlines Logo
12:10 p.m. - 5:00 a.m.YWG-SJU
14h 50m2 stops
American Airlines Logo
5:24 a.m. - 11:35 p.m.SJU-YWG
20h 11m3 stops
C$ 2,478American Airlines
Find Deal
Sat, 27 Dec - Sat, 3 Jan

WestJet flights from Winnipeg to Puerto Rico

Our best WestJet deals on Winnipeg to Puerto Rico flight tickets
WestJet
3 Mar
YWG5:00 a.m.Winnipeg
16h 49m
2 stops
SJU11:49 p.m.San Juan Luis Munoz Marin Intl
4 Mar
SJU7:30 a.m.San Juan Luis Munoz Marin Intl
9h 39m
1 stop
YWG3:09 p.m.Winnipeg
C$ 908
Find similar
WestJet
3 Mar
YWG5:00 a.m.Winnipeg
16h 49m
2 stops
SJU11:49 p.m.San Juan Luis Munoz Marin Intl
4 Mar
SJU7:30 a.m.San Juan Luis Munoz Marin Intl
9h 39m
1 stop
YWG3:09 p.m.Winnipeg
C$ 910
Find similar
WestJet
3 Mar
YWG5:00 a.m.Winnipeg
16h 49m
2 stops
SJU11:49 p.m.San Juan Luis Munoz Marin Intl
4 Mar
SJU7:30 a.m.San Juan Luis Munoz Marin Intl
30h 02m
2 stops
YWG11:32 a.m.Winnipeg
C$ 918
Find similar

United Airlines flights from Winnipeg to Puerto Rico

Our best United Airlines deals on Winnipeg to Puerto Rico flight tickets
United Airlines
3 Mar
YWG7:15 a.m.Winnipeg
13h 07m
2 stops
SJU10:22 p.m.San Juan Luis Munoz Marin Intl
3 Mar
SJU2:05 a.m.San Juan Luis Munoz Marin Intl
12h 34m
2 stops
YWG12:39 p.m.Winnipeg
C$ 1,107
Find similar
United Airlines
25 Nov
YWG2:20 p.m.Winnipeg
30h 02m
2 stops
SJU10:22 p.m.San Juan Luis Munoz Marin Intl
1 Dec
SJU2:05 a.m.San Juan Luis Munoz Marin Intl
17h 14m
2 stops
YWG5:19 p.m.Winnipeg
C$ 1,139
Find similar

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 October 2025.
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

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 25/11

8:00 a.m.-12:24 a.m.

1 stop14h 24m

San Juan Luis Munoz Marin Intl

Tue 2/12

7:20 a.m.-5:26 p.m.

1 stop12h 06m

C$ 666

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 25/11

8:00 a.m.-12:24 a.m.

1 stop14h 24m

San Juan Luis Munoz Marin Intl

Tue 2/12

4:48 p.m.-3:07 p.m.

2 stops24h 19m

C$ 671

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 3/3

5:00 a.m.-11:49 p.m.

2 stops16h 49m

San Juan Luis Munoz Marin Intl

Wed 4/3

7:30 a.m.-3:09 p.m.

1 stop9h 39m

C$ 908

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 3/3

5:00 a.m.-11:49 p.m.

2 stops16h 49m

San Juan Luis Munoz Marin Intl

Wed 4/3

7:30 a.m.-3:09 p.m.

1 stop9h 39m

C$ 910

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 3/3

7:15 a.m.-10:22 p.m.

2 stops13h 07m

San Juan Luis Munoz Marin Intl

Tue 3/3

2:05 a.m.-12:39 p.m.

2 stops12h 34m

C$ 1,107

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 25/11

2:20 p.m.-10:22 p.m.

2 stops30h 02m

San Juan Luis Munoz Marin Intl

Mon 1/12

2:05 a.m.-5:19 p.m.

2 stops17h 14m

C$ 1,139

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 27/12

7:05 p.m.-2:40 p.m.

1 stop17h 35m

San Juan Luis Munoz Marin Intl

Fri 2/1

2:05 a.m.-4:35 p.m.

2 stops16h 30m

C$ 2,000

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 27/12

7:05 p.m.-2:40 p.m.

1 stop17h 35m

San Juan Luis Munoz Marin Intl

Fri 2/1

2:05 a.m.-4:35 p.m.

2 stops16h 30m

C$ 2,002

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 27/12

12:10 p.m.-9:36 a.m.

3 stops19h 26m

San Juan Luis Munoz Marin Intl

Sat 3/1

5:24 a.m.-11:35 p.m.

3 stops20h 11m

C$ 2,451

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 27/12

12:10 p.m.-5:00 a.m.

2 stops14h 50m

San Juan Luis Munoz Marin Intl

Sat 3/1

5:24 a.m.-11:35 p.m.

3 stops20h 11m

C$ 2,478

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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 April, then flying in May is also cheap. Prices for this month can be found on momondo for an average of C$ 766.

What is the cheapest day to depart on your flight to Puerto Rico?

The cheapest day to depart from Winnipeg to Puerto Rico is on a Tuesday. Travellers who choose to depart for Puerto Rico on a Tuesday will often find tickets for as low as C$ 806. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 1,083. These prices are subject to change though, so be sure to set up a Price Alert for flights to Puerto Rico.

What is the cheapest time of day to depart on your flight to Puerto Rico?

The cheapest time of day to fly to Puerto Rico is in the afternoon when flights can be purchased for as low as C$ 804. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are C$ 934 on average. Flights to Puerto Rico from Winnipeg in the morning are generally more expensive because this time of day is more convenient for travellers’ schedules.

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

You could potentially save up to 24% 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

Direct flights

None
There are no direct flights from Winnipeg to Puerto Rico. There are no popular flight routes from Winnipeg to Puerto Rico.
Search flight deals

  • 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
United AirlinesPriceFrom C$ 509Free CancellationRating
7.4
8,973 reviews
Search United Airlines flights
WestJetPriceFrom C$ 756Free CancellationRating
7.2
3,124 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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Wed 12/11
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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$ 336
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