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Cheap flights from Winnipeg to San Juan from C$ 294

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 18/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
2 Dec — 9 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Winnipeg to San Juan

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to San Juan
Explore the most affordable flight options available from Winnipeg to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 2 November 2025.

Wed 19/117:30 a.m.YWG - SJU
2 stops31h 51mMultiple Airlines
Fri 28/116:01 a.m.SJU - YWG
1 stop11h 06mMultiple Airlines
Deal found 31/10C$ 524
Sun 16/117:30 a.m.YWG - SJU
2 stops30h 40mMultiple Airlines
Fri 28/116:01 a.m.SJU - YWG
1 stop11h 06mMultiple Airlines
Deal found 31/10C$ 527
Wed 19/117:30 a.m.YWG - SJU
2 stops18h 03mMultiple Airlines
Thu 27/114:05 p.m.SJU - YWG
1 stop25h 02mMultiple Airlines
Deal found 31/10C$ 566
Fri 5/127:30 a.m.YWG - SJU
1 stop29h 28mMultiple Airlines
Wed 10/124:31 p.m.SJU - YWG
2 stops34h 10mMultiple Airlines
Deal found 31/10C$ 590
Wed 3/127:30 a.m.YWG - SJU
2 stops27h 02mMultiple Airlines
Sun 7/124:10 a.m.SJU - YWG
1 stop15h 53mMultiple Airlines
Deal found 31/10C$ 598
Sun 16/117:30 a.m.YWG - SJU
1 stop29h 49mMultiple Airlines
Thu 27/118:00 a.m.SJU - YWG
2 stops33h 07mMultiple Airlines
Deal found 31/10C$ 609
Sat 15/116:55 p.m.YWG - SJU
2 stops18h 24mMultiple Airlines
Fri 28/116:01 a.m.SJU - YWG
1 stop11h 06mMultiple Airlines
Deal found 31/10C$ 611
Thu 4/129:00 p.m.YWG - SJU
2 stops16h 21mMultiple Airlines
Mon 8/121:59 a.m.SJU - YWG
2 stops39h 08mMultiple Airlines
Deal found 31/10C$ 619
Thu 4/129:00 p.m.YWG - SJU
2 stops16h 21mMultiple Airlines
Sun 7/124:10 a.m.SJU - YWG
1 stop15h 53mMultiple Airlines
Deal found 31/10C$ 630
Fri 5/127:30 a.m.YWG - SJU
1 stop29h 28mMultiple Airlines
Sun 7/124:10 a.m.SJU - YWG
1 stop15h 53mMultiple Airlines
Deal found 31/10C$ 653

Cheap flight deals from Winnipeg to San Juan

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 2 November 2025.

Round-trip from

C$ 524

One-way from

C$ 294

Popular in

December

Cheapest in

April

Average price

C$ 904
19/11-28/11
  • 19/11-28/11
  • 3 total stops
  • 42h 57m total
  • Winnipeg to San Juan
Search Deals
18/4
  • 18/4
  • 2 total stops
  • 13h 08m total
  • Winnipeg to San Juan
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 144 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to San Juan that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 2 November 2025.
Use the filters below to find and compare flights from Winnipeg to San Juan that are best for you.

Fly from

Winnipeg

Fly to

San Juan

Route

Depart

Return

Price

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 16/11

7:30 a.m.-4:10 p.m.

2 stops30h 40m

San Juan Luis Munoz Marin Intl

Fri 28/11

6:01 a.m.-3:07 p.m.

1 stop11h 06m

C$ 527

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 18/1

7:30 a.m.-1:44 a.m.

2 stops40h 14m

San Juan Luis Munoz Marin Intl

Sat 24/1

7:52 p.m.-3:07 p.m.

1 stop21h 15m

C$ 573

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 5/12

7:30 a.m.-12:45 a.m.

2 stops15h 15m

San Juan Luis Munoz Marin Intl

Sun 7/12

4:10 a.m.-6:03 p.m.

1 stop15h 53m

C$ 598

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 3/3

8:15 a.m.-12:36 a.m.

2 stops14h 21m

San Juan Luis Munoz Marin Intl

Wed 4/3

7:35 p.m.-4:35 p.m.

2 stops23h 00m

C$ 728

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 24/1

8:20 p.m.-2:09 p.m.

1 stop15h 49m

San Juan Luis Munoz Marin Intl

Sat 31/1

7:52 p.m.-3:09 p.m.

1 stop21h 17m

C$ 731

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 18/4

5:00 a.m.-7:08 p.m.

2 stops13h 08m

C$ 294

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 24/1

12:20 p.m.-2:50 a.m.

2 stops12h 30m

C$ 338

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 18/4

12:20 p.m.-1:00 p.m.

1 stop23h 40m

C$ 356

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 3/4

7:30 a.m.-12:00 p.m.

1 stop27h 30m

C$ 528

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 3/4

12:10 p.m.-8:36 a.m.

3 stops19h 26m

C$ 887

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Best time to book a flight from Winnipeg to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan from Winnipeg with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to San Juan

What is the cheapest month to book a flight from Winnipeg to San Juan?

Currently, May is the cheapest month in which you can book a flight from Winnipeg to San Juan (average of C$ 412). Flying from Winnipeg to San Juan in October is currently the most expensive (average of C$ 856). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YWG to SJU?

Find hourly flight availability from Winnipeg to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 2 November 2025.

One of the essential ways to save on airfare from Winnipeg to San Juan is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 13% on airfare.

Reviews of airlines servicing San Juan

Get insights into the airlines that provide service to San Juan. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Juan. Reviews last updated 2 November 2025.
See what other customers who have flown with United Airlines and WestJet from Winnipeg to San Juan have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,993 reviews
Check prices

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,993 reviews
United Airlines
7.4
Good
8,993 reviews
Check prices

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
WestJet
7.2
Good
3,153 reviews
United Airlines
7.4
Good
8,993 reviews
Check prices

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to San Juan. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Winnipeg to San Juan?

    Located just 7.3 km from the city centre, Winnipeg is the airport most travellers will use when flying to San Juan from Winnipeg. Booking flights from Winnipeg (YWG) to San Juan should be relatively easy as there are 0 daily outbound flights to San Juan from 2 different airlines.

  • How long is the flight from Winnipeg to San Juan?

    There are many flights that can get you from Winnipeg to San Juan in 14h 21m. Fly via Air Canada to get the fastest option. The distance between Winnipeg and San Juan is about 4461 km.

  • What are the cheapest airlines flying from Winnipeg to San Juan round-trip?

    According to our current data, United Airlines (C$ 509), and WestJet (C$ 757) offers the cheapest pricing from Winnipeg to San Juan. United Airlines is currently priced 42% below the average price you’ll pay for this route.

  • Can I find deals for flights from Winnipeg to San Juan that include hotel bookings?

    Yes. In addition to deals on Winnipeg to San Juan flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to San Juan?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to San Juan.

  • Can I find deals for business class flights from Winnipeg to San Juan?

    Yes. Cheapflights offers flight deals from Winnipeg to San Juan by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Winnipeg to San Juan?

    Currently, May is the cheapest month in which you can book a flight from Winnipeg to San Juan (average of C$ 412). Flying from Winnipeg to San Juan in October is currently the most expensive (average of C$ 856). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Winnipeg to San Juan

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to Luis Munoz Marin Intl flights

Top 2 airlines flying from Winnipeg to San Juan

Discover the top 2 airlines that operate flights from Winnipeg to San Juan. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 2 November 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 509AverageC$ 780FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 757AverageC$ 887FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Winnipeg to San Juan?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Winnipeg to San Juan. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to San Juan?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to San Juan from Winnipeg.

Can Cheapflights find flights from Winnipeg to San Juan with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Winnipeg to San Juan flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Winnipeg to San Juan become cheaper?

Yes! Start tracking prices for Winnipeg to San Juan flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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