C$ 410 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 14/3. 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

Sun, 1 Mar - Wed, 4 Mar
Air Canada Logo
2:20 p.m. - 9:00 p.m.
YWG
-
SJU
28h 40m
1 stop
Air Canada Logo
8:30 a.m. - 11:57 a.m.
SJU
-
YWG
29h 27m
1 stop
C$ 642Air Canada
Sun, 1 Mar - Wed, 4 Mar
Air Canada Logo
2:20 p.m. - 9:00 p.m.
YWG
-
SJU
28h 40m
1 stop
Air Canada Logo
8:30 a.m. - 11:57 a.m.
SJU
-
YWG
29h 27m
1 stop
C$ 643Air Canada
Sun, 1 Mar - Wed, 4 Mar
Air Canada Logo
8:15 a.m. - 12:36 a.m.
YWG
-
SJU
14h 21m
2 stops
Air Canada Logo
8:30 a.m. - 11:57 a.m.
SJU
-
YWG
29h 27m
1 stop
C$ 652Air Canada
Sun, 1 Mar - Wed, 4 Mar
Air Canada Logo
2:20 p.m. - 9:00 p.m.
YWG
-
SJU
28h 40m
1 stop
Air Canada Logo
5:50 p.m. - 9:44 a.m.
SJU
-
YWG
17h 54m
2 stops
C$ 653Air Canada
Sun, 1 Mar - Wed, 4 Mar
Air Canada Logo
2:20 p.m. - 9:00 p.m.
YWG
-
SJU
28h 40m
1 stop
Air Canada Logo
5:50 p.m. - 9:44 a.m.
SJU
-
YWG
17h 54m
2 stops
C$ 654Air Canada
Sun, 15 Mar - Tue, 31 Mar
Multiple Airlines Logo
7:30 a.m. - 11:29 a.m.
YWG
-
SJU
26h 59m
1 stop
Multiple Airlines Logo
7:00 a.m. - 11:32 a.m.
SJU
-
YWG
29h 32m
2 stops
C$ 662Multiple Airlines
Sun, 1 Mar - Wed, 4 Mar
Air Canada Logo
8:15 a.m. - 12:36 a.m.
YWG
-
SJU
14h 21m
2 stops
Air Canada Logo
5:50 p.m. - 9:44 a.m.
SJU
-
YWG
17h 54m
2 stops
C$ 664Air Canada
Sun, 1 Mar - Wed, 4 Mar
Air Canada Logo
2:20 p.m. - 9:00 p.m.
YWG
-
SJU
28h 40m
1 stop
Air Canada Logo
8:30 a.m. - 11:57 a.m.
SJU
-
YWG
29h 27m
1 stop
C$ 698Air Canada
Sun, 1 Mar - Sat, 14 Mar
Multiple Airlines Logo
7:30 a.m. - 3:02 p.m.
YWG
-
SJU
29h 32m
1 stop
Multiple Airlines Logo
1:45 a.m. - 3:09 p.m.
SJU
-
YWG
14h 24m
2 stops
C$ 702Multiple Airlines
Sun, 15 Mar - Tue, 31 Mar
Multiple Airlines Logo
8:15 a.m. - 12:17 a.m.
YWG
-
SJU
15h 02m
2 stops
Multiple Airlines Logo
7:00 a.m. - 11:32 a.m.
SJU
-
YWG
29h 32m
2 stops
C$ 703Multiple Airlines
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Good to know

Low seasonApril
Best time to beat the crowds (26% 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.

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 3253 reviews
6.1Entertainment
7.0Comfort
7.9Crew
6.2Food
7.4Boarding
Airline reviews

Everything was great until we had to get our bags. The bags came out in several different batches over 90 minutes after we landed maybe more we got our bags. So much for the old West Jet where they promised bags in 20 minutes. I Next time I will pack lighter and go with a carry-on.

6.0 GoodMike, Jan 2026
YYC - SJD
Read more WestJet reviews

Everything was great until we had to get our bags. The bags came out in several different batches over 90 minutes after we landed maybe more we got our bags. So much for the old West Jet where they promised bags in 20 minutes. I Next time I will pack lighter and go with a carry-on.

Flight left on time. The crew was very friendly. I had to buy a proper meal. Small cookie and a drink just doesn’t cut it for a 4.5 hours flight.

The flight was full and good as could be expected. We arrived early which is always a good thing.

Experience was good, the wifi hook up is somewhat tough

Plane was one hour late. Hardly any space for our carry-ons. Stressful to catch connections.

The delays were never ending and we were never properly informed as to why. 1st and 2nd delay were handled well, but by the time we received our 7th delay, and then subsequently asked to willingly get bumped, it turned into one of the worst flying situations of my life. I didn’t get home until 2am which is roughly 5 hours later than originally planned.

Great flight, great landing, nice staff. Our seats were a little cramped.

I will not be flying with westjet again. I was uncomfortable in my seat. The position made my back hurt so bad. My wife was able to fit the seatbelt around her with out an extension but was unable to put the tray table down or fit in the seat for that matter. Our bag was smashed and I spent two hours trying to fill out the application for a damaged bag before I gave up. The 80 photos I took would not work and nothing telling me the format to upload them as.. I made the mistake of unpacking the bag before taking photos so no claim for me. Next trip to Canada I will have to use air Canada.

No food, water, snacks.”beverages”. This was on Christmas Day. Upgrading cost $100, for what exactly?

Overall good experience. The wait for baggage at our destination was quite long, but other than that everything was good as expected

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

Information on your arrival and departure airports

Winnipeg (YWG)