C$ 314 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 13/6. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Puerto Rico

Travellers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 27% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights Deals

Cheap Flight Deals from Winnipeg to Puerto Rico (YWG-PR0)

 
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.

Recent round-trip flight deals from Winnipeg to Puerto Rico

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Winnipeg to Puerto Rico.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
12:52 p.m. - 4:33 p.m.YWG-SJU
26h 41m2 stops
Delta Logo
12:50 p.m. - 11:57 a.m.SJU-YWG
24h 07m2 stops
C$ 591Delta
Find Deal
Tue, 20 May - Tue, 27 May
 Logo
9:00 a.m. - 11:31 a.m.YWG-SJU
25h 31m1 stop
 Logo
9:30 p.m. - 12:25 p.m.SJU-YWG
15h 55m2 stops
C$ 678
Find Deal
Tue, 13 May - Tue, 20 May
WestJet Logo
9:00 a.m. - 10:47 p.m.YWG-SJU
12h 47m1 stop
WestJet Logo
7:30 a.m. - 4:28 p.m.SJU-YWG
9h 58m1 stop
C$ 810WestJet
Find Deal
Tue, 13 May - Tue, 20 May
WestJet Logo
6:30 a.m. - 10:47 p.m.YWG-SJU
15h 17m2 stops
WestJet Logo
7:30 a.m. - 12:13 a.m.SJU-YWG
17h 43m2 stops
C$ 828WestJet
Find Deal
Tue, 13 May - Tue, 20 May
United Airlines Logo
2:20 p.m. - 11:54 p.m.YWG-SJU
8h 34m1 stop
United Airlines Logo
2:05 a.m. - 1:09 p.m.SJU-YWG
12h 04m2 stops
C$ 835United Airlines
Find Deal
Tue, 20 May - Mon, 26 May
WestJet Logo
9:00 a.m. - 10:47 p.m.YWG-SJU
12h 47m1 stop
WestJet Logo
7:00 a.m. - 12:13 a.m.SJU-YWG
18h 13m2 stops
C$ 844WestJet
Find Deal
Tue, 20 May - Tue, 27 May
WestJet Logo
9:00 a.m. - 10:47 p.m.YWG-SJU
12h 47m1 stop
WestJet Logo
2:31 p.m. - 4:28 p.m.SJU-YWG
26h 57m1 stop
C$ 878WestJet
Find Deal
Tue, 20 May - Tue, 27 May
United Airlines Logo
2:20 p.m. - 11:54 p.m.YWG-SJU
8h 34m1 stop
United Airlines Logo
1:05 a.m. - 3:31 p.m.SJU-YWG
15h 26m2 stops
C$ 879United Airlines
Find Deal
Tue, 13 May - Mon, 19 May
United Airlines Logo
4:25 p.m. - 11:54 p.m.YWG-SJU
30h 29m2 stops
United Airlines Logo
2:05 a.m. - 1:09 p.m.SJU-YWG
12h 04m2 stops
C$ 944United Airlines
Find Deal
Tue, 20 May - Mon, 26 May
United Airlines Logo
7:40 a.m. - 11:54 p.m.YWG-SJU
15h 14m2 stops
United Airlines Logo
1:05 a.m. - 3:31 p.m.SJU-YWG
15h 26m2 stops
C$ 963United Airlines
Find Deal
Tue, 13 May - Mon, 19 May
Useful Info

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$ 655 (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$ 1,181 and C$ 1,026 respectively.


Good to know

Low seasonJune
High seasonJanuary
Cheapest flightC$ 314
Best time to beat the crowds (12% less expensive on average)
Most popular time to fly and prices are also 0% 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 8696 reviews
7.3Comfort
7.7Boarding
7.1Entertainment
8.1Crew
6.6Food
Airline reviews

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

2.0 MediocreBrant, Apr 2025YHZ - EWR
Read more United Airlines reviews

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 as good as expected Air Can needs to improve totally rated on internet as worst

The flight was delayed, it took longer than anticipated because of weather, and they broke my luggage.

My husband required a wheelchair to get to the airplane and the service he received was exemplary. Thank you.

Internet on both flights was sketchy. Thus in flight entertainment was non- existent on MN - Balrimote leg.

crew was great, wifi was very poor could not even load a youtube video

WestJet was able to re-book us to the next available flight at no charge when air traffic controller staffing shortage delayed our inbound flight

Our flight was delayed for almost 2 hours resulting in a rush to connect to our next flight

I am a tall woman and could not move my legs enough to reach down under the seat in front of me to retrieve anything I put down there. I sat in both aisle and window seats and felt extremely cramped. In the aisle seat, if the stewardess was heavy, it was impossible to pass, and she would knock my arm shoulder and thigh every time she went by. If I can avoid it, I will not be flying this airline again.

We never had an experience they canceled the flight and they did not offer us an alternative flight. I had to book one on my own expense. They offered us food voucher and we could not use them at the airport it kept saying not attached to an existing flight. The people at the counter were rude and cold and they did not care about our situation

It took 30 minutes to check in with the Westjet rep. They didn’t have enough seats and she needed to make a call… I am always “randomly” selected to be checked at security. Their “randomly “ selection system may need some updating. They treat people like criminals. It is not appropriate behavior.

Get our, as a group, skis on time to their destination. Have more attendants checking people in. There was only one. The line was a block long :( . Also flight change with 5-hour delay

Found the seats very crowded—too close together ! And waited a long time for our luggage All staff at both ends were excellent!!!

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.