C$ 276 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 24/10. 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

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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

mar., 3 mar. - mié., 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$ 889WestJet
Find Deal
mar., 3 mar. - mié., 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$ 891WestJet
Find Deal
mar., 3 mar. - mié., 4 mar.
WestJet Logo
5:00 a.m. - 11:49 p.m.YWG-SJU
16h 49m2 stops
WestJet Logo
7:30 a.m. - 12:35 a.m.SJU-YWG
19h 05m2 stops
C$ 898WestJet
Find Deal
mar., 3 mar. - mié., 4 mar.
WestJet Logo
5:00 a.m. - 11:49 p.m.YWG-SJU
16h 49m2 stops
WestJet Logo
7:30 a.m. - 11:32 a.m.SJU-YWG
30h 02m2 stops
C$ 901WestJet
Find Deal
mar., 3 mar. - mar., 3 mar.
United Airlines Logo
7:15 a.m. - 10:22 p.m.YWG-SJU
13h 07m2 stops
United Airlines Logo
2:05 a.m. - 11:39 a.m.SJU-YWG
11h 34m2 stops
C$ 923United Airlines
Find Deal
mar., 3 mar. - mar., 3 mar.
United Airlines Logo
7:15 a.m. - 9:00 p.m.YWG-SJU
11h 45m2 stops
United Airlines Logo
2:05 a.m. - 11:39 a.m.SJU-YWG
11h 34m2 stops
C$ 925United Airlines
Find Deal
mar., 3 mar. - mié., 4 mar.
United Airlines Logo
7:15 a.m. - 9:00 p.m.YWG-SJU
11h 45m2 stops
United Airlines Logo
5:50 p.m. - 11:39 a.m.SJU-YWG
19h 49m2 stops
C$ 950United Airlines
Find Deal
sáb., 27 dic. - vie., 2 ene.
Air Canada Logo
7:05 p.m. - 2:50 p.m.YWG-SJU
17h 45m1 stop
Air Canada Logo
2:05 a.m. - 4:35 p.m.SJU-YWG
16h 30m2 stops
C$ 1,897Air Canada
Find Deal
sáb., 27 dic. - vie., 2 ene.
Air Canada Logo
7:05 p.m. - 1:55 p.m.YWG-SJU
16h 50m2 stops
Air Canada Logo
2:05 a.m. - 4:35 p.m.SJU-YWG
16h 30m2 stops
C$ 1,902Air Canada
Find Deal
sáb., 27 dic. - vie., 2 ene.
Air Canada Logo
7:05 p.m. - 2:50 p.m.YWG-SJU
17h 45m1 stop
Air Canada Logo
2:05 a.m. - 4:35 p.m.SJU-YWG
16h 30m2 stops
C$ 1,985Air Canada
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$ 641 (return) on average. On the other hand, the most expensive months are October and December, when the average cost of round-trip tickets is C$ 1,182 and C$ 1,082 respectively.

Good to know

Low seasonJuly
Best time to beat the crowds (11% less expensive on average)
Most popular time to fly and prices are also 3% 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$ 574 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$ 667.

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 8937 reviews
8.1Crew
7.1Entertainment
7.3Comfort
6.6Food
7.7Boarding
Airline reviews

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

10.0 ExcellentPaulos, Aug 2025YUL - IAD
Read more United Airlines reviews

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

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

So far so good but food and entertainment are not available for this flight

Plane temperature was comfortable (not to hot) when boarding and waiting for takeoff.

The experience was good just the upcharge of over a hundred dollars was not cool.

No internet, not even westjet connect makes for a boring flight

Our first flight from LAX to Winnipeg was changed but you never informed us at all. It went from a nonstop flight to a stay at Calgary. This impacted our trip negatively as we arrived much later than we planned to. Our returning flight was horrible. The flight was delayed 6 hours!! And we were NOT going to wait that long. The only way we got on our original flight was running there. However all of our suitcases were now coming on the delayed flight. It was the worst experience we ever had flying. I want my money back.

Typical Canadian airline experience. Charger and tray were broken, food was poor quality, and yet you're still paying more than flights with equal to better service than elsewhere globally.

Good, a bit cramped in the seat as my neighbour was a bit large

There was a man who was very rude at boarding. On the other hand personal bag measuring box is too small compared to USA airlines,

While I appreciated the food (it was unexpected), it was interruptive for sleeping. We paid extra for reserved seats, but when we checked in they gave us different seats. I had to call WestJet arounf 11:30pm the night before our flight to get this fixed. We were give seats in the emengency row to resolve the issue.

Not enough food option. And not enough advices or information about what we are gonna eat.

Please make more option. And be more precise on the type of food you giving. Diner and breakfast can be different

I like how spacious the plane was but I did not like the fact that there was no entertainment

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

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