C$ 451 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 25/7. 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

Fri, 11 Jul - Thu, 17 Jul
 Logo
9:00 a.m. - 3:25 p.m.YWG-SJU
29h 25m1 stop
 Logo
2:40 a.m. - 4:23 p.m.SJU-YWG
14h 43m2 stops
C$ 572
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Fri, 11 Jul - Thu, 17 Jul
 Logo
9:00 a.m. - 1:35 a.m.YWG-SJU
15h 35m2 stops
 Logo
2:40 a.m. - 4:23 p.m.SJU-YWG
14h 43m2 stops
C$ 576
Find Deal
Fri, 11 Jul - Fri, 18 Jul
Delta Logo
8:35 a.m. - 11:59 p.m.YWG-SJU
14h 24m2 stops
Delta Logo
6:15 a.m. - 8:10 p.m.SJU-YWG
14h 55m2 stops
C$ 630Delta
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Sat, 23 Aug - Sat, 30 Aug
Delta Logo
12:43 p.m. - 11:40 a.m.YWG-SJU
21h 57m2 stops
Delta Logo
2:40 p.m. - 11:51 a.m.SJU-YWG
22h 11m2 stops
C$ 643Delta
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Sat, 18 Oct - Sun, 26 Oct
Air Canada Logo
7:55 a.m. - 12:34 p.m.YWG-SJU
27h 39m2 stops
Air Canada Logo
2:45 p.m. - 3:13 p.m.SJU-YWG
25h 28m2 stops
C$ 660Air Canada
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Thu, 21 Aug - Mon, 25 Aug
WestJet Logo
5:45 p.m. - 10:07 p.m.YWG-SJU
27h 22m2 stops
WestJet Logo
7:30 a.m. - 12:13 a.m.SJU-YWG
17h 43m2 stops
C$ 902WestJet
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Wed, 20 Aug - Mon, 25 Aug
WestJet Logo
6:30 a.m. - 10:07 p.m.YWG-SJU
14h 37m2 stops
WestJet Logo
7:30 a.m. - 9:43 a.m.SJU-YWG
27h 13m2 stops
C$ 904WestJet
Find Deal
Sat, 18 Oct - Sat, 25 Oct
United Airlines Logo
7:40 a.m. - 11:57 p.m.YWG-SJU
15h 17m2 stops
United Airlines Logo
1:05 a.m. - 3:58 p.m.SJU-YWG
15h 53m2 stops
C$ 947United Airlines
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Thu, 21 Aug - Sun, 24 Aug
United Airlines Logo
4:25 p.m. - 2:44 p.m.YWG-SJU
21h 19m2 stops
United Airlines Logo
1:05 a.m. - 11:28 p.m.SJU-YWG
23h 23m2 stops
C$ 1,038United Airlines
Find Deal
Sat, 18 Oct - Sun, 26 Oct
Air Canada Logo
7:00 a.m. - 2:44 p.m.YWG-SJU
30h 44m1 stop
Air Canada Logo
2:45 p.m. - 8:58 p.m.SJU-YWG
31h 13m1 stop
C$ 1,122Air Canada
Find Deal
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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$ 647 (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$ 1,166 and C$ 1,013 respectively.


Good to know

Low seasonJune
High seasonJanuary
Cheapest flightC$ 451
Best time to beat the crowds (11% less expensive on average)
Most popular time to fly and prices are also 1% lower on average.
Flight from Winnipeg to San Juan

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.

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 8790 reviews
7.0Entertainment
8.1Crew
7.3Comfort
7.7Boarding
6.6Food
Airline reviews

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

10.0 ExcellentAnonymous, May 2025YVR - SFO
Read more United Airlines reviews

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.

Michael, our FA was very attentive, even finding me a chocolate brownie from economy class when the dessert selections were all dairy based. ( intolerant, not allergic so don’t usually need to order dairy free)

We tried to upgrade to economy premium but were told this was not possible as we had booked through United Airlines (and Air Canada was operating the flight). This seemed silly given there was ample space in economy premium. Additionally, we had to wait almost 1.5 hours upon arrival to taxi to the gate. Otherwise, the crew were very pleasant and passengers were friendly.

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

headphone jack didnt work for the first flight and not much variety

Plane 3 hours late. Missed connection. No help from gate staff. App horrible. Lost connection repeatedly. No service desk. Finally got help from young girl driving cart.

Not the greatest experience everything was pretty mediocre. My seat was by the washroom in the aisle and was not located well as everyone past each other people were right in my seat and space.

Lots of overhead storage, good crew, good service, smooth landing.

Lots of overhead storage and a good crew and service.

The small prop plane was crowded and the overhead luggage storage is a smaller than on the jets. Other than that, the crew was good, the flight was on time and the landing was smooth.

There was a medical emergency that the crew handled very well. There was no “entertainment” of any sort-no movie/music/whatever. Food was typical of airlines: mediocre.

On time. Friendly and efficient staff at check in and flight crew.

Terrible decision to take a night flight. Not enough time to sleep and premium seat has no foot rest ao couldn’t get comfortable!

Late departure, so I missed connection in Detroit. But Delta gave me a great hotel & breakfast. Just sorry I could not get anything from my checked baggage.

Crew was friendly. Lost our luggage and told us it’d be in later in the evening of the day we returned. It was not. Still after 5 days have not received it.

Was on a Swoop plane. No wifi and no Westjet connect

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

Information on your arrival and departure airports

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