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Cheap flights from Winnipeg to San Juan from C$ 342

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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SJU
21 May — 28 May1
1 adult
1 adult, Economy, 0 bags

Cheap 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 21 April 2026.

Tue 22/97:00 a.m.
YWG
-
SJU
1 stop30h 44m
Air Canada
Thu 24/91:00 a.m.
SJU
-
YWG
2 stops23h 07m
Air Canada
Deal found 19/4C$ 654
Sun 3/55:10 p.m.
YWG
-
SJU
2 stops19h 35m
Air Canada
Thu 7/56:45 p.m.
SJU
-
YWG
2 stops17h 23m
Air Canada
Deal found 16/4C$ 784
Thu 4/611:40 a.m.
YWG
-
SJU
3 stops27h 40m
Multiple Airlines
Thu 11/62:37 p.m.
SJU
-
YWG
3 stops35h 18m
Multiple Airlines
Deal found 20/4C$ 804
Sun 3/56:30 p.m.
YWG
-
SJU
2 stops17h 22m
WestJet
Thu 7/57:05 a.m.
SJU
-
YWG
2 stops27h 40m
WestJet
Deal found 19/4C$ 833
Mon 4/511:40 a.m.
YWG
-
SJU
2 stops11h 39m
Multiple Airlines
Thu 7/58:04 p.m.
SJU
-
YWG
3 stops29h 51m
Multiple Airlines
Deal found 20/4C$ 904
Mon 4/54:25 p.m.
YWG
-
SJU
2 stops19h 27m
WestJet
Thu 7/57:05 a.m.
SJU
-
YWG
2 stops32h 20m
WestJet
Deal found 20/4C$ 938
Thu 21/56:15 a.m.
YWG
-
SJU
2 stops13h 15m
WestJet
Thu 28/52:35 p.m.
SJU
-
YWG
2 stops52h 35m
WestJet
Deal found 21/4C$ 1,000

Find 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 21 April 2026.

Round-trip from

C$ 654

One-way from

C$ 342

Popular in

December

Cheapest in

July

Average price

C$ 827
Air Canada
  • Air Canada
  • 22/9-24/9
  • 3 total stops
  • 53h 51m total
  • Winnipeg to San Juan
Search Deals
1/6
  • 1/6
  • 2 total stops
  • 32h 40m total
  • Winnipeg to San Juan
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 148 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 52 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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 21 April 2026.
Use the filters below to find and compare flights from Winnipeg to San Juan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Tue 22/9

7:00 a.m.-2:44 p.m.

1 stop30h 44m

San Juan Luis Munoz Marin Intl

Thu 24/9

1:00 a.m.-11:07 p.m.

2 stops23h 07m

C$ 654
Quickest round-trip

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 3/5

5:10 p.m.-1:45 p.m.

2 stops19h 35m

San Juan Luis Munoz Marin Intl

Thu 7/5

6:45 p.m.-11:08 a.m.

2 stops17h 23m

C$ 784

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 3/5

6:30 p.m.-12:52 p.m.

2 stops17h 22m

San Juan Luis Munoz Marin Intl

Thu 7/5

7:05 a.m.-9:45 a.m.

2 stops27h 40m

C$ 833

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 21/5

6:15 a.m.-8:30 p.m.

2 stops13h 15m

San Juan Luis Munoz Marin Intl

Thu 28/5

2:35 p.m.-6:10 p.m.

2 stops52h 35m

C$ 1,000

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sun 3/5

8:45 a.m.-5:38 p.m.

1 stop31h 53m

San Juan Luis Munoz Marin Intl

Wed 6/5

1:00 a.m.-11:52 a.m.

2 stops11h 52m

C$ 1,042
Cheapest one-way

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 1/6

9:05 p.m.-4:01 a.m.

3 stops29h 56m

C$ 346
Quickest one-way

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 1/6

7:00 a.m.-8:34 p.m.

1 stop12h 34m

C$ 491

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/4

Sorted by cheapest first

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
No data available for this route at this time. Please check back soon.

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 21 April 2026.
See what other customers who have flown with 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.
WestJet
7.2
Good
3,323 reviews
Check prices

Crew

7.9

Boarding

7.4

Food

6.2

Entertainment

6.1

Comfort

7.0

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..
WestJet
7.2
Good
3,323 reviews
WestJet
7.2
Good
3,323 reviews
Check prices

Crew

7.9

Boarding

7.4

Food

6.2

Entertainment

6.1

Comfort

7.0

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Joseph,Feb 2026

YYJ - YEG

Is just a domestic flight can't complain at all..but everything is great..

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 1 airline.

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

    There are many flights that can get you from Winnipeg to San Juan in 30h 44m. Fly via Air Canada to get the fastest option. The distance between Winnipeg and San Juan is about 4461 km.

  • What is the cheapest airline to fly from Winnipeg to San Juan round-trip?

    According to our current data, WestJet (C$ 757), offers the cheapest pricing from Winnipeg to San Juan. WestJet is currently priced 17% 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.

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 airline flying from Winnipeg to San Juan

Discover the top airline 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 21 April 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 757AverageC$ 892FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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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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