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Cheap flights from Winnipeg to San Juan from C$ 338

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 24/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
27 Aug — 3 Sep1
1 adult

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 22 August 2025.

Round-trip from

C$ 774

One-way from

C$ 338

Popular in

August

Cheapest in

April

Average price

C$ 1,194
Delta
  • Delta
  • 8/1-14/1
  • 4 total stops
  • 51h 44m total
  • Winnipeg to San Juan
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24/10
  • 24/10
  • 3 total stops
  • 28h 12m total
  • Winnipeg to San Juan
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Highest demand for flights based on searches. 1% potential increase in price (C$ 15 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 39 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Winnipeg to San Juan

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 22 August 2025.

Thu 27/115:00 a.m.YWG - SJU
2 stops16h 17mWestJet
Sat 6/127:30 a.m.SJU - YWG
2 stops19h 12mWestJet
Deal found 20/8C$ 843
Thu 27/1112:20 p.m.YWG - SJU
2 stops12h 34mMultiple Airlines
Sat 6/123:59 p.m.SJU - YWG
1 stop25h 08mMultiple Airlines
Deal found 20/8C$ 856
Fri 3/1010:45 a.m.YWG - SJU
2 stops24h 03mWestJet
Mon 6/107:00 a.m.SJU - YWG
2 stops31h 43mWestJet
Deal found 20/8C$ 882
Thu 27/118:40 a.m.YWG - SJU
1 stop31h 45mUnited Airlines
Fri 5/122:05 a.m.SJU - YWG
2 stops12h 34mUnited Airlines
Deal found 20/8C$ 960
Fri 3/102:20 p.m.YWG - SJU
1 stop23h 24mUnited Airlines
Sun 5/101:05 a.m.SJU - YWG
2 stops23h 20mUnited Airlines
Deal found 20/8C$ 968
Fri 19/128:00 a.m.YWG - SJU
2 stops33h 08mMultiple Airlines
Sat 10/17:52 p.m.SJU - YWG
1 stop21h 15mMultiple Airlines
Deal found 20/8C$ 1,132
Fri 19/128:05 p.m.YWG - SJU
2 stops25h 54mWestJet
Sat 10/16:15 a.m.SJU - YWG
2 stops38h 57mWestJet
Deal found 20/8C$ 1,183
Fri 19/128:40 a.m.YWG - SJU
2 stops19h 31mUnited Airlines
Fri 9/12:05 a.m.SJU - YWG
2 stops23h 39mUnited Airlines
Deal found 20/8C$ 1,496
Sat 23/82:35 p.m.YWG - SJU
2 stops24h 52mWestJet
Mon 1/97:00 a.m.SJU - YWG
2 stops27h 41mWestJet
Deal found 21/8C$ 1,871

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 22 August 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

Thu 8/1

5:38 p.m.-11:49 p.m.

2 stops28h 11m

San Juan Luis Munoz Marin Intl

Wed 14/1

2:10 p.m.-11:43 a.m.

2 stops23h 33m

C$ 774

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 7/1

7:30 a.m.-5:19 p.m.

1 stop7h 49m

San Juan Luis Munoz Marin Intl

Wed 14/1

3:30 p.m.-7:12 p.m.

2 stops29h 42m

C$ 796

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 8/1

8:05 p.m.-2:15 p.m.

2 stops16h 10m

San Juan Luis Munoz Marin Intl

Wed 14/1

7:30 a.m.-3:07 p.m.

1 stop9h 37m

C$ 833

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 27/11

5:00 a.m.-11:17 p.m.

2 stops16h 17m

San Juan Luis Munoz Marin Intl

Sat 6/12

7:30 a.m.-12:42 a.m.

2 stops19h 12m

C$ 843

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 27/11

12:20 p.m.-2:54 a.m.

2 stops12h 34m

San Juan Luis Munoz Marin Intl

Sat 6/12

3:59 p.m.-3:07 p.m.

1 stop25h 08m

C$ 856

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 3/10

10:45 a.m.-11:48 a.m.

2 stops24h 03m

San Juan Luis Munoz Marin Intl

Mon 6/10

7:00 a.m.-1:43 p.m.

2 stops31h 43m

C$ 882

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 4/2

7:30 a.m.-5:15 p.m.

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Sun 15/2

6:15 a.m.-3:09 p.m.

1 stop10h 54m

C$ 943

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 27/11

8:40 a.m.-6:25 p.m.

1 stop31h 45m

San Juan Luis Munoz Marin Intl

Fri 5/12

2:05 a.m.-12:39 p.m.

2 stops12h 34m

C$ 960

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 3/10

4:25 p.m.-8:38 p.m.

2 stops27h 13m

San Juan Luis Munoz Marin Intl

Sun 5/10

1:05 a.m.-11:25 p.m.

2 stops23h 20m

C$ 968

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 24/10

9:00 a.m.-2:12 p.m.

3 stops28h 12m

C$ 338

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/8

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, April is the cheapest month in which you can book a flight from Winnipeg to San Juan (average of C$ 254). Flying from Winnipeg to San Juan in July is currently the most expensive (average of C$ 580). 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 22 August 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 at noon could potentially save you up to 14% 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 22 August 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
8,934 reviews
Check prices

Boarding

7.7

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2024

YVR - SFO

It was a good experience. The flight took 45 minutes longer to fly and all passengers had to wait inside the plane till the technical issue was fixed. Overall it was a good experience.
United Airlines
7.4
Good
8,934 reviews
United Airlines
7.4
Good
8,934 reviews
Check prices

Boarding

7.7

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2024

YVR - SFO

It was a good experience. The flight took 45 minutes longer to fly and all passengers had to wait inside the plane till the technical issue was fixed. Overall it was a good experience.
WestJet
7.2
Good
3,044 reviews
United Airlines
7.4
Good
8,934 reviews
Check prices

Boarding

7.7

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Dec 2024

YVR - SFO

It was a good experience. The flight took 45 minutes longer to fly and all passengers had to wait inside the plane till the technical issue was fixed. Overall it was a good experience.

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 7h 49m. Fly via Delta or WestJet to get the fastest option. The distance between Winnipeg and San Juan is about 4461 km. Both multi-stop and direct flights can be found to your destination and back.

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

    According to our current data, United Airlines (C$ 500), and WestJet (C$ 750) offers the cheapest pricing from Winnipeg to San Juan. United Airlines is currently priced 44% 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, April is the cheapest month in which you can book a flight from Winnipeg to San Juan (average of C$ 254). Flying from Winnipeg to San Juan in July is currently the most expensive (average of C$ 580). 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

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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 22 August 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 500AverageC$ 774FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 750AverageC$ 874FlexibilityNo 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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