What is the cheapest airline that flies from Windsor to Caribbean Islands?

Air Canada and WestJet are the most popular carriers operating from Windsor to Caribbean Islands

When did momondo last update prices for flights from Windsor Airport to Caribbean Islands?

Prices for flights from Windsor Airport to Caribbean Islands are updated daily.

How many operators does momondo search for flights from Windsor Airport to Caribbean Islands?

As of June 2026, there is 1 operator available to choose from for flights from Windsor Airport to Caribbean Islands.

How old do you have to be to fly from Windsor Airport to Caribbean Islands?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Windsor Airport to Caribbean Islands.

What documentation or ID do you need to fly to Caribbean Islands?

The travel and health documents required for your trip to Caribbean Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

C$ 369 Cheap Flights from Windsor, Ontario to Caribbean Islands in 2026

Find the cheapest flights from Windsor, Ontario to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

4:05 p.m. - 1:45 p.m.

YQG

SJU

21h 40m

2 stops

1:00 a.m. - 7:02 p.m.

SJU

YQG

18h 02m

2 stops

C$ 633Air Canada

Sat, 26 Sep - Mon, 28 Sep

10:05 a.m. - 12:54 p.m.

YQG

SJU

26h 49m

2 stops

1:00 a.m. - 7:07 p.m.

SJU

YQG

18h 07m

2 stops

C$ 637Air Canada

Sat, 19 Sep - Mon, 21 Sep

10:05 a.m. - 12:54 p.m.

YQG

SJU

26h 49m

2 stops

1:00 a.m. - 7:07 p.m.

SJU

YQG

18h 07m

2 stops

C$ 638Air Canada

Sat, 19 Sep - Mon, 21 Sep

10:05 a.m. - 12:54 p.m.

YQG

SJU

26h 49m

2 stops

1:00 a.m. - 7:07 p.m.

SJU

YQG

18h 07m

2 stops

C$ 640Air Canada

Sat, 19 Sep - Mon, 21 Sep

7:45 p.m. - 3:25 p.m.

YQG

PUJ

19h 40m

1 stop

4:20 p.m. - 7:02 p.m.

PUJ

YQG

26h 42m

1 stop

C$ 698Air Canada

Mon, 3 Aug - Mon, 10 Aug

7:45 p.m. - 3:15 p.m.

YQG

PUJ

19h 30m

1 stop

4:20 p.m. - 9:22 a.m.

PUJ

YQG

17h 02m

1 stop

C$ 700Air Canada

Sat, 4 Jul - Mon, 13 Jul

7:45 p.m. - 4:05 p.m.

YQG

PUJ

20h 20m

2 stops

4:20 p.m. - 9:22 a.m.

PUJ

YQG

17h 02m

1 stop

C$ 702Air Canada

Mon, 3 Aug - Mon, 10 Aug

7:45 p.m. - 3:20 p.m.

YQG

PUJ

19h 35m

1 stop

4:20 p.m. - 3:22 p.m.

PUJ

YQG

23h 02m

1 stop

C$ 703Air Canada

Mon, 19 Oct - Thu, 22 Oct

4:30 p.m. - 6:30 p.m.

YQG

MBJ

27h 00m

2 stops

7:30 p.m. - 3:46 p.m.

MBJ

YQG

19h 16m

2 stops

C$ 1,208Multiple Airlines

Fri, 14 Aug - Sat, 29 Aug

4:00 p.m. - 11:53 p.m.

YQG

SJU

31h 53m

2 stops

2:31 p.m. - 3:10 p.m.

SJU

YQG

48h 39m

2 stops

C$ 1,971WestJet

Sat, 1 Aug - Sat, 8 Aug

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Air Canada flights from Windsor, Ontario to Caribbean Islands

Our best Air Canada deals on Windsor, Ontario to Caribbean Islands flight tickets

Air Canada

26 Sep

YQG4:05 p.m.Windsor

21h 40m

2 stops

SJU1:45 p.m.San Juan Luis Munoz Marin Intl

28 Sep

SJU1:00 a.m.San Juan Luis Munoz Marin Intl

18h 02m

2 stops

YQG7:02 p.m.Windsor

C$ 633

Air Canada

19 Sep

YQG10:05 a.m.Windsor

26h 49m

2 stops

SJU12:54 p.m.San Juan Luis Munoz Marin Intl

21 Sep

SJU1:00 a.m.San Juan Luis Munoz Marin Intl

18h 07m

2 stops

YQG7:07 p.m.Windsor

C$ 637

Air Canada

19 Sep

YQG10:05 a.m.Windsor

26h 49m

2 stops

SJU12:54 p.m.San Juan Luis Munoz Marin Intl

21 Sep

SJU1:00 a.m.San Juan Luis Munoz Marin Intl

18h 07m

2 stops

YQG7:07 p.m.Windsor

C$ 638

WestJet flights from Windsor, Ontario to Caribbean Islands

Our best WestJet deals on Windsor, Ontario to Caribbean Islands flight tickets

WestJet

15 Aug

YQG4:00 p.m.Windsor

27h 30m

2 stops

MBJ6:30 p.m.Montego Bay Sangster Intl

30 Aug

MBJ7:30 p.m.Montego Bay Sangster Intl

18h 40m

2 stops

YQG3:10 p.m.Windsor

C$ 1,418

WestJet

1 Aug

YQG4:00 p.m.Windsor

31h 53m

2 stops

SJU11:53 p.m.San Juan Luis Munoz Marin Intl

8 Aug

SJU2:31 p.m.San Juan Luis Munoz Marin Intl

48h 39m

2 stops

YQG3:10 p.m.Windsor

C$ 1,971

momondo Fare Finder

Use the filters below to find and compare flights from Windsor, Ontario to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Sat 26/9

4:05 p.m.-1:45 p.m.

2 stops21h 40m

San Juan Luis Munoz Marin Intl

Mon 28/9

1:00 a.m.-7:02 p.m.

2 stops18h 02m

C$ 633

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Sat 19/9

10:05 a.m.-12:54 p.m.

2 stops26h 49m

San Juan Luis Munoz Marin Intl

Mon 21/9

1:00 a.m.-7:07 p.m.

2 stops18h 07m

C$ 637

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Sat 19/9

10:05 a.m.-12:54 p.m.

2 stops26h 49m

San Juan Luis Munoz Marin Intl

Mon 21/9

1:00 a.m.-7:07 p.m.

2 stops18h 07m

C$ 638

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Sat 19/9

10:05 a.m.-12:54 p.m.

2 stops26h 49m

San Juan Luis Munoz Marin Intl

Mon 21/9

1:00 a.m.-7:07 p.m.

2 stops18h 07m

C$ 640

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 3/8

7:45 p.m.-3:25 p.m.

1 stop19h 40m

Punta Cana

Mon 10/8

4:20 p.m.-7:02 p.m.

1 stop26h 42m

C$ 698

Quickest round-trip

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Sat 4/7

7:45 p.m.-3:15 p.m.

1 stop19h 30m

Punta Cana

Mon 13/7

4:20 p.m.-9:22 a.m.

1 stop17h 02m

C$ 700

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 3/8

7:45 p.m.-4:05 p.m.

2 stops20h 20m

Punta Cana

Mon 10/8

4:20 p.m.-9:22 a.m.

1 stop17h 02m

C$ 702

WindsorPunta Cana

YQG - PUJ

YQGPUJ

Windsor

Mon 19/10

7:45 p.m.-3:20 p.m.

1 stop19h 35m

Punta Cana

Thu 22/10

4:20 p.m.-3:22 p.m.

1 stop23h 02m

C$ 703

WindsorMontego Bay

YQG - MBJ

YQGMBJ

Windsor

Fri 14/8

4:30 p.m.-6:30 p.m.

2 stops27h 00m

Montego Bay Sangster Intl

Sat 29/8

7:30 p.m.-3:46 p.m.

2 stops19h 16m

C$ 1,208

WindsorSan Juan

YQG - SJU

YQGSJU

Windsor

Sat 1/8

4:00 p.m.-11:53 p.m.

2 stops31h 53m

San Juan Luis Munoz Marin Intl

Sat 8/8

2:31 p.m.-3:10 p.m.

2 stops48h 39m

C$ 1,971

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Windsor, Ontario to Caribbean Islands

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

Prices

Airlines

What is the cheapest Windsor to Caribbean Islands flight route?

Fly from Windsor to Punta Cana for the best Windsor - Caribbean Islands flight prices

What cabin class options are available on Windsor, Ontario to Caribbean Islands flights?

There is only 1 cabin class available to choose from on Windsor, Ontario to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Windsor, Ontario to Caribbean Islands flights?

You could potentially save up to 18% on your flight if you consider stops on a Windsor, Ontario to Caribbean Islands flight.

Cheap Windsor, Ontario to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Windsor, Ontario to Caribbean Islands

Fastest flight time	16h 35m
Direct flights	None

The fastest flight from Windsor, Ontario to Caribbean Islands takes 16h 35m

There are no direct flights from Windsor, Ontario to Caribbean Islands. There are no popular flight routes from Windsor, Ontario to Caribbean Islands.

Search flight deals

Frequently asked questions about flying from Windsor, Ontario to Caribbean Islands

When did momondo last update prices for flights from Windsor Airport to Caribbean Islands?
Prices for flights from Windsor Airport to Caribbean Islands are updated daily.
How many operators does momondo search for flights from Windsor Airport to Caribbean Islands?
As of June 2026, there is 1 operator available to choose from for flights from Windsor Airport to Caribbean Islands.
How old do you have to be to fly from Windsor Airport to Caribbean Islands?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Windsor Airport to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The travel and health documents required for your trip to Caribbean Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Windsor, Ontario to Caribbean Islands?
momondo data reveals that the most frequently booked plane model on the route from Windsor, Ontario to Caribbean Islands is De Havilland (Bombardier) DHC-8-400 Dash 8Q, representing 55.56% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 14.38%, Boeing 737-700 Passenger/BBJ1 (winglets) at 11.55%, and Airbus A321-100/200 at 2.40%.

Best airlines flying from Windsor, Ontario to Caribbean Islands

Compare and see reviews for airlines that fly from Windsor, Ontario to Caribbean Islands with momondo

Airline	Rating	Free Cancellation	Price
Air Transat	PriceFrom C$ 745	Free Cancellation	Rating 7.8 556 reviews		Search Air Transat flights

Why use momondo?

Why should I use momondo to find a flight deal from Windsor to Caribbean Islands?

It is quick and easy to find Windsor to Caribbean Islands 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 Caribbean Islands that suits you.

Can I find flights from Windsor to Caribbean Islands with flexible booking policies on momondo?

Yes. All flights to Caribbean Islands from Windsor on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Windsor to Caribbean Islands?

Once you have performed a search for Windsor to Caribbean Islands flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Windsor to Caribbean Islands right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Windsor to Caribbean Islands 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.