Cheap flights from Winnipeg to Caribbean from C$ 309
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 Caribbean departing on 23/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names, great deals
Big names, great deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Early arrival? Instantly customize your resultsTrusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Winnipeg to Caribbean
Cheap round-trip flights
Cheap one-way flights
Cheap last-minute flights
Delta flights from Winnipeg to Caribbean
Our best Delta deals on Winnipeg to Caribbean flight tickets
Air Canada flights from Winnipeg to Caribbean
Our best Air Canada deals on Winnipeg to Caribbean flight tickets
How to get the cheapest flight ticket from Winnipeg to Caribbean
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 Caribbean?
In general, June is the cheapest month to fly from Winnipeg to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 667. If you don’t want to visit Caribbean in June, then you should wait until October to fly from Winnipeg, when ticket prices are also cheap, with an average price of C$ 710.
What is the cheapest day to depart on your flight to Caribbean?
On average, the least expensive day to fly to Caribbean from Winnipeg is on a Monday. momondo users have found tickets for Monday departures for as low as C$ 780. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Caribbean on Sunday is C$ 1,178.
What is the cheapest time of day to depart on your flight to Caribbean?
Our data shows that the cheapest Winnipeg to Caribbean flights are usually those with departure times in the afternoon. Our users have found flights to Caribbean in the afternoon for as low as C$ 783. In the morning is when there is more demand to fly to Caribbean, so prices are often more expensive at around C$ 1,132 per ticket.
What is the cheapest Winnipeg to Caribbean flight route?
Fly from Winnipeg to Montego Bay Sangster Intl for the best Winnipeg - Caribbean flight prices
How far in advance should I book a flight to Caribbean?
You are more likely to see cheaper flights to Caribbean from Winnipeg when booking 3 weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around C$ 779 when searching 3 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Winnipeg for as low as C$ 718 on momondo.
What cabin class options are available on Winnipeg to Caribbean flights?
There are 1 cabin classes available to choose from on Winnipeg to Caribbean flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Winnipeg to Caribbean?
WestJet, United Airlines, and Air Canada are the most popular carriers operating from Winnipeg to Caribbean
Which airlines fly to Caribbean?
WestJet, Air Canada and United Airlines are the top three most popular airlines that fly to Caribbean from Winnipeg according to our data. WestJet is the first choice among our users, with 71% of people opting to fly with this airline when travelling to Caribbean. Keep in mind that there are 5 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.
Cheap Winnipeg to Caribbean flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Caribbean
When did momondo last update prices for flights from Winnipeg Airport to Caribbean?
Prices for flights from Winnipeg Airport to Caribbean were last updated today.
How many operators does momondo search for flights from Winnipeg Airport to Caribbean?
As of June 2025, there are 5 operators available to choose from for flights from Winnipeg Airport to Caribbean.
How old do you have to be to fly from Winnipeg Airport to Caribbean?
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 Winnipeg Airport to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The necessary travel and health documents for your Caribbean 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.
What is the most popular plane model from Winnipeg to Caribbean?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Winnipeg to Caribbean is Boeing 737-700 Passenger/BBJ1 (winglets) (45.95% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (32.43%), Boeing 737-800 (Scimitar Winglets) (13.51%), and Boeing 737-800 Passenger/BBJ2 (winglets) (8.11%).
Best airlines flying from Winnipeg to Caribbean
Compare and see reviews for airlines that fly from Winnipeg to Caribbean with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom C$ 460 | Free Cancellation | Rating 7.2 2,868 reviews | |||
| PriceFrom C$ 465 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom C$ 481 | Free Cancellation | Rating 7.1 9,537 reviews | |||
| PriceFrom C$ 700 | Free Cancellation | Rating 6.7 36 reviews | |||
| PriceFrom C$ 795 | Free Cancellation | Rating 7.8 396 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Winnipeg to Caribbean?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Caribbean from Winnipeg.
Can I find flights from Winnipeg to Caribbean with flexible booking policies on momondo?
Flights from Winnipeg to Caribbean with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Winnipeg to Caribbean?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Caribbean from Winnipeg.
I’m not ready to book a flight from Winnipeg to Caribbean right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Caribbean, momondo offers a useful price alert feature which will track prices for flights to Caribbean from Winnipeg and alert you when they change.