C$ 564 Find Cheap Flights from Winnipeg to Puerto Rico – Compare and Save

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, 0 bags

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Flight Deals

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

Mon, 19 Oct - Fri, 23 Oct
Air Canada Logo
3:20 p.m. - 1:45 p.m.
YWG
-
SJU
21h 25m
2 stops
Air Canada Logo
3:56 p.m. - 10:33 p.m.
SJU
-
YWG
31h 37m
1 stop
C$ 698Air Canada
Mon, 19 Oct - Fri, 23 Oct
Air Canada Logo
3:20 p.m. - 1:45 p.m.
YWG
-
SJU
21h 25m
2 stops
Air Canada Logo
3:56 p.m. - 10:33 p.m.
SJU
-
YWG
31h 37m
1 stop
C$ 699Air Canada
Mon, 21 Sep - Fri, 25 Sep
Air Canada Logo
7:10 p.m. - 1:53 p.m.
YWG
-
SJU
17h 43m
2 stops
Air Canada Logo
3:56 p.m. - 12:37 p.m.
SJU
-
YWG
21h 41m
1 stop
C$ 701Air Canada
Mon, 19 Oct - Thu, 22 Oct
Air Canada Logo
2:05 p.m. - 11:57 a.m.
YWG
-
SJU
20h 52m
2 stops
Air Canada Logo
1:00 a.m. - 4:17 p.m.
SJU
-
YWG
16h 17m
2 stops
C$ 709Air Canada
Mon, 19 Oct - Fri, 23 Oct
Air Canada Logo
3:20 p.m. - 11:57 a.m.
YWG
-
SJU
19h 37m
2 stops
Air Canada Logo
6:45 p.m. - 4:17 p.m.
SJU
-
YWG
22h 32m
2 stops
C$ 710Air Canada
Mon, 21 Sep - Fri, 25 Sep
Air Canada Logo
3:20 p.m. - 1:53 p.m.
YWG
-
SJU
21h 33m
2 stops
Air Canada Logo
6:45 p.m. - 2:22 p.m.
SJU
-
YWG
20h 37m
2 stops
C$ 712Air Canada
Mon, 21 Sep - Fri, 25 Sep
United Airlines Logo
2:00 p.m. - 2:44 p.m.
YWG
-
SJU
23h 44m
1 stop
United Airlines Logo
3:56 p.m. - 10:33 p.m.
SJU
-
YWG
31h 37m
1 stop
C$ 888United Airlines
Mon, 19 Oct - Fri, 23 Oct
United Airlines Logo
8:45 a.m. - 5:38 p.m.
YWG
-
SJU
31h 53m
1 stop
United Airlines Logo
3:56 p.m. - 12:37 p.m.
SJU
-
YWG
21h 41m
1 stop
C$ 965United Airlines
Mon, 6 Jul - Fri, 10 Jul
United Airlines Logo
12:56 p.m. - 9:24 p.m.
YWG
-
SJU
31h 28m
2 stops
United Airlines Logo
1:00 a.m. - 11:52 a.m.
SJU
-
YWG
11h 52m
2 stops
C$ 983United Airlines
Mon, 19 Oct - Fri, 23 Oct
United Airlines Logo
8:45 a.m. - 5:38 p.m.
YWG
-
SJU
31h 53m
1 stop
United Airlines Logo
3:56 p.m. - 12:37 p.m.
SJU
-
YWG
21h 41m
1 stop
C$ 1,031United Airlines
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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.

Reviews of the top airline 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.
7.2
WestJetOverall score based on 3361 reviews
7.4Boarding
7.9Crew
6.2Food
6.1Entertainment
7.0Comfort
Airline reviews

Despite travelling ultra basic for the first time due to such increased rates we both managed with one bag each. Even boarding last wasn’t SO bad.

10.0 ExcellentKimberley, Jun 2026
YYC - LAS
Read more WestJet reviews

Despite travelling ultra basic for the first time due to such increased rates we both managed with one bag each. Even boarding last wasn’t SO bad.

There was no food but a singular cookie for a flight that was over 5hours??? Yeah not fun I was starving and again super cramped plane and you guys need to get planes with screens too, WiFi is nice but common we need more

I loved the fact it was on time and it was a smooth flight to my destination.

I like that we landed safely and that my dog was safe underneath as well. Outside of that, we were 45 mins late for a direct flight that is 1.5 hours long. And 2 of my 3 bags did not make the flight. Only my dog was onboard.

Service was okay except attendant over served alcohol to passenger and passenger got tipsy and made me uncomfortable

Food was not inspired but was satisfying. Same for infotainment selection. You’d think business class would come with complimentary WiFi. Crew was uniformly attentive and excellent.

Could not make the flight. No one would help us at all

Decent entertainment although my wife was not offered any ear buds so couldn’t enjoy. Real issue was the appalling food. Presentation was unacceptable with cheap hard to open packaged bread, plastic cheese again in hard to open shrink wrap, main course in small cardboard box again hard to open, wooden utensils which lack substance making the whole experience poor. Surprised I didn’t cover myself or neighbour as the food moved all over the place. Breakfast calzone was dry and unappealing with the staff basically throwing them around. Very disappointed

Better movie options. More diligence on the size and amount of bags people bring on board. Lady across aisle from me had a bucket style bag that would only go so far under the seat in front of her. She was not told once that the whole bag is supposed to be under the seat. Crew is very hardworking however.

I didn’t have any food but my Prosecco hit the spot. We left on time and the crew was friendly.

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

Information on your arrival and departure airports

Winnipeg (YWG)