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Cheap flights from Winnipeg to San Juan from C$ 487

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to San Juan departing on 27/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Winnipeg to San Juan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:00 a.m. - 1:37 a.m.YWG-SJU
18h 37m3 stops
Multiple Airlines Logo
3:36 p.m. - 11:13 a.m.SJU-YWG
20h 37m3 stops
C$ 691Multiple Airlines
Find Deal
Wed, 4 Mar - Thu, 12 Mar
United Airlines Logo
8:40 a.m. - 12:36 a.m.YWG-SJU
13h 56m2 stops
United Airlines Logo
2:05 a.m. - 11:57 a.m.SJU-YWG
11h 52m2 stops
C$ 693United Airlines
Find Deal
Mon, 8 Dec - Wed, 10 Dec
WestJet Logo
12:20 p.m. - 2:09 p.m.YWG-SJU
23h 49m1 stop
WestJet Logo
3:00 p.m. - 12:42 a.m.SJU-YWG
11h 42m1 stop
C$ 694WestJet
Find Deal
Sat, 13 Dec - Sun, 21 Dec
WestJet Logo
12:20 p.m. - 2:09 p.m.YWG-SJU
23h 49m1 stop
WestJet Logo
7:30 a.m. - 11:35 a.m.SJU-YWG
30h 05m2 stops
C$ 727WestJet
Find Deal
Sat, 13 Dec - Sun, 21 Dec
Multiple Airlines Logo
5:00 a.m. - 1:37 a.m.YWG-SJU
18h 37m3 stops
Multiple Airlines Logo
7:05 p.m. - 4:35 p.m.SJU-YWG
22h 30m2 stops
C$ 728Multiple Airlines
Find Deal
Wed, 4 Mar - Thu, 12 Mar
Multiple Airlines Logo
12:20 p.m. - 2:50 a.m.YWG-SJU
12h 30m2 stops
Multiple Airlines Logo
8:37 p.m. - 7:09 p.m.SJU-YWG
23h 32m2 stops
C$ 734Multiple Airlines
Find Deal
Thu, 19 Feb - Sun, 8 Mar
Multiple Airlines Logo
5:00 a.m. - 1:37 a.m.YWG-SJU
18h 37m3 stops
Multiple Airlines Logo
1:29 a.m. - 11:35 p.m.SJU-YWG
23h 06m2 stops
C$ 807Multiple Airlines
Find Deal
Wed, 4 Mar - Wed, 11 Mar
Air Canada Logo
5:30 a.m. - 9:00 p.m.YWG-SJU
13h 30m2 stops
Air Canada Logo
8:10 a.m. - 11:57 a.m.SJU-YWG
29h 47m1 stop
C$ 842Air Canada
Find Deal
Mon, 8 Dec - Thu, 11 Dec
WestJet Logo
9:05 a.m. - 2:00 p.m.YWG-SJU
50h 55m2 stops
WestJet Logo
2:16 p.m. - 11:32 a.m.SJU-YWG
47h 16m2 stops
C$ 849WestJet
Find Deal
Fri, 6 Feb - Fri, 13 Feb
WestJet Logo
12:55 p.m. - 2:00 p.m.YWG-SJU
47h 05m2 stops
WestJet Logo
7:30 a.m. - 3:09 p.m.SJU-YWG
9h 39m1 stop
C$ 852WestJet
Find Deal
Fri, 6 Feb - Fri, 13 Feb

United Airlines flights from Winnipeg to San Juan

Our best United Airlines deals on Winnipeg to San Juan flight tickets
United Airlines
8 Dec
YWG8:40 a.m.Winnipeg
13h 56m
2 stops
SJU12:36 a.m.San Juan Luis Munoz Marin Intl
10 Dec
SJU2:05 a.m.San Juan Luis Munoz Marin Intl
11h 52m
2 stops
YWG11:57 a.m.Winnipeg
C$ 693
Find similar
United Airlines
8 Dec
YWG5:30 a.m.Winnipeg
13h 30m
2 stops
SJU9:00 p.m.San Juan Luis Munoz Marin Intl
10 Dec
SJU2:05 a.m.San Juan Luis Munoz Marin Intl
11h 52m
2 stops
YWG11:57 a.m.Winnipeg
C$ 858
Find similar
United Airlines
8 Dec
YWG2:20 p.m.Winnipeg
23h 20m
1 stop
SJU3:40 p.m.San Juan Luis Munoz Marin Intl
10 Dec
SJU2:05 a.m.San Juan Luis Munoz Marin Intl
11h 52m
2 stops
YWG11:57 a.m.Winnipeg
C$ 913
Find similar

WestJet flights from Winnipeg to San Juan

Our best WestJet deals on Winnipeg to San Juan flight tickets
WestJet
13 Dec
YWG12:20 p.m.Winnipeg
23h 49m
1 stop
SJU2:09 p.m.San Juan Luis Munoz Marin Intl
21 Dec
SJU3:00 p.m.San Juan Luis Munoz Marin Intl
11h 42m
1 stop
YWG12:42 a.m.Winnipeg
C$ 694
Find similar
WestJet
13 Dec
YWG12:20 p.m.Winnipeg
23h 49m
1 stop
SJU2:09 p.m.San Juan Luis Munoz Marin Intl
21 Dec
SJU7:30 a.m.San Juan Luis Munoz Marin Intl
30h 05m
2 stops
YWG11:35 a.m.Winnipeg
C$ 727
Find similar
WestJet
6 Feb
YWG9:05 a.m.Winnipeg
50h 55m
2 stops
SJU2:00 p.m.San Juan Luis Munoz Marin Intl
13 Feb
SJU2:16 p.m.San Juan Luis Munoz Marin Intl
47h 16m
2 stops
YWG11:32 a.m.Winnipeg
C$ 849
Find similar

momondo 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, momondo users made 96,600 searches. Data last updated 26 November 2025.
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

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 4/3

5:00 a.m.-1:37 a.m.

3 stops18h 37m

San Juan Luis Munoz Marin Intl

Thu 12/3

3:36 p.m.-11:13 a.m.

3 stops20h 37m

C$ 691

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 8/12

8:40 a.m.-12:36 a.m.

2 stops13h 56m

San Juan Luis Munoz Marin Intl

Wed 10/12

2:05 a.m.-11:57 a.m.

2 stops11h 52m

C$ 693

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 13/12

12:20 p.m.-2:09 p.m.

1 stop23h 49m

San Juan Luis Munoz Marin Intl

Sun 21/12

3:00 p.m.-12:42 a.m.

1 stop11h 42m

C$ 694

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Sat 13/12

12:20 p.m.-2:09 p.m.

1 stop23h 49m

San Juan Luis Munoz Marin Intl

Sun 21/12

7:30 a.m.-11:35 a.m.

2 stops30h 05m

C$ 727

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 4/3

5:00 a.m.-1:37 a.m.

3 stops18h 37m

San Juan Luis Munoz Marin Intl

Thu 12/3

7:05 p.m.-4:35 p.m.

2 stops22h 30m

C$ 728

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Thu 19/2

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

2 stops12h 30m

San Juan Luis Munoz Marin Intl

Sun 8/3

8:37 p.m.-7:09 p.m.

2 stops23h 32m

C$ 734

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Wed 4/3

5:00 a.m.-1:37 a.m.

3 stops18h 37m

San Juan Luis Munoz Marin Intl

Wed 11/3

1:29 a.m.-11:35 p.m.

2 stops23h 06m

C$ 807

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Mon 8/12

5:30 a.m.-9:00 p.m.

2 stops13h 30m

San Juan Luis Munoz Marin Intl

Thu 11/12

8:10 a.m.-11:57 a.m.

1 stop29h 47m

C$ 842

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 6/2

9:05 a.m.-2:00 p.m.

2 stops50h 55m

San Juan Luis Munoz Marin Intl

Fri 13/2

2:16 p.m.-11:32 a.m.

2 stops47h 16m

C$ 849

WinnipegSan Juan

YWG - SJU

YWGSJU

Winnipeg

Fri 6/2

12:55 p.m.-2:00 p.m.

2 stops47h 05m

San Juan Luis Munoz Marin Intl

Fri 13/2

7:30 a.m.-3:09 p.m.

1 stop9h 39m

C$ 852

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to San Juan from

How to get the cheapest flight ticket from Winnipeg to San Juan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to San Juan?

The month of April is, on average, the cheapest month to fly to San Juan from Winnipeg, with most prices found around C$ 667. If you aren’t able to travel to San Juan during the month of April, then flying in May is also cheap. Prices for this month can be found on momondo for an average of C$ 772.

What is the cheapest day to depart on your flight to San Juan?

According to our data, Tuesday is the cheapest day to fly to San Juan from Winnipeg. The lowest ticket price found for a Tuesday departure recently was C$ 812. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Winnipeg because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 1,091.

What is the cheapest time of day to depart on your flight to San Juan?

Our most recent data shows that the best time of day to fly to San Juan is in the afternoon. Flights from Winnipeg to San Juan during this time can be as low as C$ 811. In the morning is when there is more demand to fly to San Juan, so prices are often more expensive at around C$ 942 per ticket.

Cheap Winnipeg to San Juan flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to San Juan

Fastest flight time

12h 30m

Direct flights

None
The fastest flight from Winnipeg to San Juan takes 12h 30m
There are no direct flights from Winnipeg to San Juan. There are no popular flight routes from Winnipeg to San Juan.
Search flight deals

  • How far is Winnipeg to San Juan by plane?

    Winnipeg and San Juan are 4446.0 km apart from one another. In terms of flight time, this usually takes a little over 8h 00m.

  • When did momondo last update prices for flights from Winnipeg Airport to San Juan?

    Prices for flights from Winnipeg Airport to San Juan are refreshed on a daily basis.

  • How many operators does momondo search for flights from Winnipeg Airport to San Juan?

  • How old do you have to be to fly from Winnipeg Airport to San Juan?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Winnipeg Airport to San Juan.

  • What documentation or ID do you need to fly to San Juan?

    The necessary travel and health documents for your San Juan trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Winnipeg to San Juan

Compare and see reviews for airlines that fly from Winnipeg to San Juan with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom C$ 513Free CancellationRating
7.4
9,046 reviews
Search United Airlines flights
WestJetPriceFrom C$ 762Free CancellationRating
7.2
3,173 reviews
Search WestJet flights

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to San Juan?

It is quick and easy to find Winnipeg to San Juan flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to San Juan that suits you.

Can I find flights from Winnipeg to San Juan with flexible booking policies on momondo?

Yes. All flights to San Juan from Winnipeg on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Winnipeg to San Juan?

momondo provides multiple filters to help you find the best flight to San Juan from Winnipeg. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Winnipeg to San Juan right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Winnipeg to San Juan flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to Puerto Rico

Fly into one of these airports located in San Juan

Airports listed have a maximum distance of 11.5 km from San Juan
San Juan Isla Grande Airport
San Juan Luis Munoz Marin Intl Airport