C$ 527 Find Cheap Flights from Winnipeg to Puerto Rico

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to Puerto Rico departing on 24/1. 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

Sat, 24 Jan - Sat, 31 Jan
Multiple Airlines Logo
6:55 p.m. - 3:06 p.m.YWG-SJU
18h 11m3 stops
Multiple Airlines Logo
4:11 p.m. - 3:09 p.m.SJU-YWG
24h 58m1 stop
C$ 554Multiple Airlines
Find Deal
Sat, 24 Jan - Sat, 31 Jan
Multiple Airlines Logo
9:00 p.m. - 3:06 p.m.YWG-SJU
16h 06m2 stops
Multiple Airlines Logo
4:11 p.m. - 3:09 p.m.SJU-YWG
24h 58m1 stop
C$ 555Multiple Airlines
Find Deal
Sat, 24 Jan - Fri, 30 Jan
United Airlines Logo
11:05 a.m. - 12:36 a.m.YWG-SJU
11h 31m2 stops
United Airlines Logo
2:05 a.m. - 11:54 p.m.SJU-YWG
23h 49m2 stops
C$ 950United Airlines
Find Deal
Mon, 10 Nov - Sat, 22 Nov
United Airlines Logo
8:40 a.m. - 12:36 a.m.YWG-SJU
13h 56m2 stops
United Airlines Logo
2:05 a.m. - 11:54 p.m.SJU-YWG
23h 49m2 stops
C$ 1,038United Airlines
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Fri, 19 Dec - Wed, 31 Dec
WestJet Logo
12:20 p.m. - 9:09 p.m.YWG-SJU
30h 49m2 stops
WestJet Logo
7:30 a.m. - 3:07 p.m.SJU-YWG
9h 37m1 stop
C$ 1,253WestJet
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Sat, 27 Dec - Sat, 3 Jan
WestJet Logo
12:20 p.m. - 5:30 p.m.YWG-SJU
27h 10m2 stops
WestJet Logo
3:30 p.m. - 7:27 p.m.SJU-YWG
29h 57m2 stops
C$ 1,281WestJet
Find Deal
Mon, 10 Nov - Sun, 23 Nov
Air Canada Logo
2:20 p.m. - 3:40 p.m.YWG-SJU
23h 20m1 stop
Air Canada Logo
4:52 p.m. - 11:57 a.m.SJU-YWG
21h 05m1 stop
C$ 1,876Air Canada
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Sat, 27 Dec - Fri, 2 Jan
Air Canada Logo
8:15 a.m. - 2:40 p.m.YWG-SJU
28h 25m2 stops
Air Canada Logo
2:05 a.m. - 4:35 p.m.SJU-YWG
16h 30m2 stops
C$ 1,999Air Canada
Find Deal
Fri, 19 Dec - Wed, 31 Dec
American Airlines Logo
6:00 a.m. - 10:05 p.m.YWG-SJU
14h 05m2 stops
American Airlines Logo
10:03 p.m. - 11:35 p.m.SJU-YWG
27h 32m3 stops
C$ 2,112American Airlines
Find Deal
Sat, 27 Dec - Sat, 3 Jan
American Airlines Logo
6:00 a.m. - 9:35 a.m.YWG-SJU
25h 35m2 stops
American Airlines Logo
5:24 a.m. - 11:35 p.m.SJU-YWG
20h 11m3 stops
C$ 2,568American Airlines
Find Deal
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$ 662 (return) on average. On the other hand, the most expensive months are December and October, when the average cost of round-trip tickets is C$ 1,180 and C$ 1,077 respectively.

Good to know

Low seasonJuly
Best time to beat the crowds (12% less expensive on average)
Most popular time to fly and prices are also 0% 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$ 804 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$ 933.

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 8996 reviews
8.1Crew
7.7Boarding
7.3Comfort
6.6Food
7.1Entertainment
Airline reviews

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

4.0 OkayAnonymous, Oct 2025YVR - SFO
Read more United Airlines reviews

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

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

Very nice and clean plane. Transit time between flights was tight though

The only thing I can't give good or really good is the fact that we didn't have food ,just a packet of pretzels or cookies which is normal,and ofcourse there isn't any entertainment. I've always flowen WestJet ..I really like the airlines..this plane was smaller one ,pretty tight seating.

Again, flight was late. It’s expected of this airline now i guess.

The ceiling leaked water on me. The toilets smelled very bad in the rear cabin

Counter representative refused to check my luggage despite paying for it in advance

We landed 26 min early. It was awesome! Smooth ride too.

When I purchased the flights I included the luggage, the luggage was not added and got charged the full price anyway. Had to pay for the luggage at check in. Initial flight was delayed, we missed our 9am connection (flew with my wife), then the airline rebooks us to the next flights, putting my wife in at 1.40pm and me at 4pm, what a crazy wait time. We managed to fix it with customer service and they put me in the 1:40pm flight too, but they left my baggage behind in the 4pm flight. When arrived to my destination, of course no luggage. It was delivered to the address thankfully late at night. The experience sucked.

Very good experience. Great cabin crew. Much better than expected

There is no snack and nit much that would be considered gluten free in yiur food selections. One of your snacks should be a gluten free cookie or small bar etc. maybe it was me but I didn’t see any free movies just internet connection and YouTube .

What do you expect from a Dash 8 plane? No seats really comfortable.

Delayed 8 hours, This is the 2nd time in a month that my flight was not on time.

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

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