C$ 309 Find Cheap Flights from Winnipeg to Puerto Rico

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to Puerto Rico departing on 23/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Winnipeg to Puerto Rico

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to Puerto Rico that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Winnipeg to Puerto Rico

Fri, 9 Jan - Fri, 16 Jan
Multiple Airlines Logo
7:30 a.m. - 1:21 a.m.
YWG
-
SJU
15h 51m1 stop
Multiple Airlines Logo
6:00 a.m. - 11:35 a.m.
SJU
-
YWG
31h 35m2 stops
C$ 657Multiple Airlines
Mon, 26 Jan - Thu, 29 Jan
Air Canada Logo
5:30 a.m. - 12:36 a.m.
YWG
-
SJU
17h 06m2 stops
Air Canada Logo
8:35 a.m. - 11:57 a.m.
SJU
-
YWG
29h 22m1 stop
C$ 711Air Canada
Mon, 26 Jan - Thu, 29 Jan
Air Canada Logo
5:30 a.m. - 12:36 a.m.
YWG
-
SJU
17h 06m2 stops
Air Canada Logo
8:35 a.m. - 11:57 a.m.
SJU
-
YWG
29h 22m1 stop
C$ 713Air Canada
Mon, 26 Jan - Thu, 29 Jan
Air Canada Logo
5:30 a.m. - 12:36 a.m.
YWG
-
SJU
17h 06m2 stops
Air Canada Logo
7:35 p.m. - 4:35 p.m.
SJU
-
YWG
23h 00m2 stops
C$ 717Air Canada
Fri, 9 Jan - Fri, 16 Jan
Multiple Airlines Logo
5:00 a.m. - 11:44 p.m.
YWG
-
SJU
16h 44m2 stops
Multiple Airlines Logo
6:00 a.m. - 11:35 a.m.
SJU
-
YWG
31h 35m2 stops
C$ 720Multiple Airlines
Sat, 24 Jan - Sun, 1 Feb
Multiple Airlines Logo
12:10 p.m. - 9:47 a.m.
YWG
-
SJU
19h 37m2 stops
Multiple Airlines Logo
8:05 p.m. - 3:30 p.m.
SJU
-
YWG
21h 25m2 stops
C$ 722Multiple Airlines
Sat, 24 Jan - Sun, 1 Feb
Multiple Airlines Logo
8:20 p.m. - 2:09 p.m.
YWG
-
SJU
15h 49m1 stop
Multiple Airlines Logo
8:05 p.m. - 11:32 a.m.
SJU
-
YWG
41h 27m2 stops
C$ 746Multiple Airlines
Sat, 24 Jan - Sun, 1 Feb
Multiple Airlines Logo
1:45 p.m. - 2:40 p.m.
YWG
-
SJU
22h 55m2 stops
Multiple Airlines Logo
4:06 p.m. - 11:32 a.m.
SJU
-
YWG
21h 26m3 stops
C$ 875Multiple Airlines
Fri, 9 Jan - Fri, 16 Jan
WestJet Logo
7:30 a.m. - 11:45 p.m.
YWG
-
SJU
14h 15m1 stop
WestJet Logo
6:15 a.m. - 3:07 p.m.
SJU
-
YWG
10h 52m1 stop
C$ 944WestJet
Sat, 24 Jan - Sun, 1 Feb
WestJet Logo
12:20 p.m. - 2:09 p.m.
YWG
-
SJU
23h 49m1 stop
WestJet Logo
7:30 a.m. - 3:09 p.m.
SJU
-
YWG
9h 39m1 stop
C$ 945WestJet
Booking Insights

KAYAK's insights & trends for Winnipeg to Puerto Rico flights

Get data-powered insights and trends into flights from Winnipeg to Puerto Rico to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Winnipeg to Puerto Rico?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Winnipeg to Puerto Rico, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Winnipeg to Puerto Rico is April, when tickets cost C$ 657 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is C$ 1,232 and C$ 938 respectively.

Good to know

Low seasonOctober
Best time to beat the crowds (6% less expensive on average)
Most popular time to fly and prices are also 5% lower on average.

FAQs - booking Puerto Rico flights

  • How does KAYAK find such low prices on flights from Winnipeg to Puerto Rico?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Winnipeg to Puerto Rico.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Winnipeg to Puerto Rico?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Winnipeg to Puerto Rico is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Winnipeg to Puerto Rico?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Winnipeg to Puerto Rico with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Winnipeg to Puerto Rico?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Winnipeg to Puerto Rico up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Puerto Rico?

    The cheapest time of day to fly to Puerto Rico is generally in the evening, when round-trip flights cost C$ 795 on average. Morning departures are around 16% more expensive than evening flights, on average. The most expensive time of day to fly to Puerto Rico is generally in the morning, which is peak travel time and where the average cost of a ticket is C$ 924.

Reviews of the top airlines flying from Winnipeg to Puerto Rico

 
Need help choosing which airline to fly with from Winnipeg to Puerto Rico? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9095 reviews
6.6Food
7.7Boarding
7.1Entertainment
8.1Crew
7.3Comfort
Airline reviews

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

8.0 ExcellentAnonymous, Dec 2025
YEG - IAH
Read more United Airlines reviews

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

Quick and seamless boarding. No entertainment but fast Starlink wifi for this short trip and the staff was really friendly.

I dread trans-Pacific flights. They are very long. This was my first time on Universal, and it was my best crossing ever. The staff were professional, the hospitality was great, and the food was delicious. The entertainment system filled the long flight hours. I will seek out Universal flights from now onwards. 🙂

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

We Left Calgary 1/2 hour late and that made for a tight connection in Denver. After arriving everything was done to help us make our connection. That was a great effort. Thank You United

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Overall, it was good. I was seating next to a wonderful lady and did not notice how time flew. Thanks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

The experience was great, the crew was very polite and hospitable. I will definitely make if my go to airlines.

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

8 hrs. Of waiting instead of couple of hours..the only good thing I'm still able to go to my destination...

Flight delayed missed connecting flight crew not very helpful very frustrating customer service

Our biggest complaint was a major schedule change that was not communicated to us in any way. Luckily the time change went later not earlier so we did not miss the flight. Our email addresses and phone numbers were on file but we received no email no text message no nothing. Short flight so not much to say.

Airplane is too small. Crew, especially the flight attendant who looked after our area, was not at all friendly and a touch authoratative. She may have been the most gruff flight attendant i've come across in 40 years of business travel

I when to Jamaica for my dad funeral and I did not get my luggage from westjet . I add to buy clothes putting me financial debt i did no want to be in Westjet did not call me to apologize are to inquire about my luggage I am still angry about it

Ground staff was not helpful, but staff at the business counter were excellent.

I selected "carry-on" for a round trip on Kayak, but my return flight on WestJet did not include a carry-on and they would not allow me to add one. My only option was to add a "checked bag" which I had to wait for on the luggage carousel after landing. Not a good experience.

The plug in to charge our phones are all loose my block would not stay in!!

My flight was cancelled due to weather but Westjet got me on a new flight in a timely and efficient manor.

It was disappointing to see the huge number of people who were allowed to board who were claiming to either be disabled or needed extra time to board who practically ran to the gate as soon as boarding opened. One of the female flight attendants in the premium economy section refused to let a lady with an infant use the toilet next to row 9 to change her baby even though the path back to the rear toilets was blocked by staff and trolleys and said she would have to carry the baby to the toilet during the descent phase when turbulence was present. The passenger refused and the baby had to wait until landing. It would have been no problem to allow this infringement of weathers petty rules. The flight was also very cold due to a cold draft throughout the flight from the bulkhead ceiling which was not controllable.

Everything you need to know for your flight from Winnipeg to Puerto Rico

Information on your arrival and departure airports