A road flanked by dense bamboo groves.

Cheap Flights to Jamaica , VT from CA $352

View CA $352 flight on Fri, Nov 6, 2026Opens in a new window

Popular airlines to Jamaica

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How much is the cheapest flight to Jamaica?

Prices were available within the past 7 days and start at CA $352 for one-way flights and CA $622 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Fri, Nov 6 - Sun, Nov 8
YYZ
Toronto
RUT
Rutland
CA $622 Roundtrip, found 8 hours ago
CA $622
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Fri, Nov 6 from Toronto to Rutland, returning Sun, Nov 8, priced at CA $622 found 8 hours ago
Delta
Wed, Sep 2 - Tue, Sep 15
YYZ
Toronto
RUT
Rutland
CA $636 Roundtrip, found 4 days ago
CA $636
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Sep 2 from Toronto to Rutland, returning Tue, Sep 15, priced at CA $636 found 4 days ago
American Airlines
Fri, Nov 6 - Sun, Nov 8
YYZ
Toronto
RUT
Rutland
CA $660 Roundtrip, found 8 hours ago
CA $660
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Fri, Nov 6 from Toronto to Rutland, returning Sun, Nov 8, priced at CA $660 found 8 hours ago
Delta
Tue, Sep 1 - Tue, Sep 15
YYZ
Toronto
RUT
Rutland
CA $663 Roundtrip, found 4 days ago
CA $663
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Sep 1 from Toronto to Rutland, returning Tue, Sep 15, priced at CA $663 found 4 days ago
American Airlines
Fri, Nov 6 - Sun, Nov 8
YYZ
Toronto
RUT
Rutland
CA $668 Roundtrip, found 8 hours ago
CA $668
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Fri, Nov 6 from Toronto to Rutland, returning Sun, Nov 8, priced at CA $668 found 8 hours ago

Frequently asked questions

What is the name of Jamaica's airport?
Logan Intl. Airport (BOS) is the main airport in Jamaica.
What airport is best to fly into Jamaica?
A flight to Jamaica means hitting the tarmac at RUT. Jump off the plane, collect your bags and you'll be 48 kilometres from the centre of town.
How many airlines fly to Jamaica?
There are a total of 43 air carriers connecting Jamaica with 122 airports across the world.
Which airlines fly to Jamaica?
Delta, JetBlue and American Airlines are the most frequent fliers to Jamaica. The majority of these flights begin in New York, with Delta having the most services on this route.
How many nonstop flights are there to Jamaica?
With 3,091 direct flights operating every week, you'll be hitting the runway in Jamaica before you have time to say, "Are we there yet?"
Where are the most popular flights to Jamaica departing from?
Flights to Jamaica departing from New York, Washington and Chicago airports are the most sought after.
How long is the flight to Jamaica Airport?
Which city you depart from determines how long you'll be strapped into your seat. From New York to Jamaica, the average flight time is 1 hour and 19 minutes. From Washington it's more or less 1 hour and 36 minutes, and from Chicago it's 2 hours and 20 minutes.
How to book the cheapest flight to Jamaica?
If you'd like to have some extra spending money on your Jamaica vacation, listen up! As any experienced traveller will tell you, avoid booking at the last minute. Prices are usually highest just prior to the departure date. Another excellent way to score the most affordable fare is to shop around. If where you're headed has multiple airports, research the cost of flying into a less busy terminal. Last of all, be ready to book quickly if you find a great price. It might not stick around for too long. With a bit of know-how and a little good fortune, the ideal airfare will be yours.
Do you have any tips for my flight to Jamaica?
If you're poorly prepared, airports and flying can be challenging. But don't hit the panic button just yet. Follow these tips and tricks and enjoy a worry-free start to your vacation in Jamaica. What to pack in your hand luggage:

  • Air travel can be a comfortable experience if you pack the right things. Firstly, you'll want a few basic toiletries, such as a toothbrush and hairbrush, a clean set of clothes and a few magazines. Next, leave space in your carry-on bag for your electronic devices, chargers, any vital medications and maybe a blow-up neck pillow too. Lastly, be sure to bring your passport, travel papers and some money.

Do not pack the following items in your hand luggage:

  • While the list of banned items differs between air carriers, the general rule of thumb is nothing sharp, flammable or explosive. This includes screwdrivers, drills, fuel and fireworks. Sporting equipment like baseball bats, and objects that could harm passengers, such as pepper spray and guns, can't come on board with you either.

What to wear on a flight:

  • Comfort should be your priority when choosing what to wear on board. Loose clothing is a smart choice, as are flat, slip-on shoes.
  • Deep vein thrombosis (DVT), a blood clot condition caused by prolonged periods of inactivity, can be a risk on long-haul flights. Try to wander around the cabin or do some gentle exercises in your seat to promote better circulation.

How to get through airport security fast when flying to Jamaica?
The simple answer is — be prepared. We've pulled together some helpful hints for an easy trip through airport security. Look out Jamaica, here you come:

  • Have your travel documents and passport within easy reach. They're the first things you'll be asked for by security.
  • Next up, both you and your carry-on bag will be X-rayed. To make the process quick and painless, take off anything that is likely to set the alarm off. Personal belongings such as your coat, belt and earphones need to go through the machine.
  • All electronic devices, including your phone and tablet, must also be scanned separately.
  • Want to bring along your favourite hand and nail cream? No problem. As long as the volume is no greater than 3.4 ounces (100 millilitres) and it's stored in a clear zip-lock bag, it's fine to bring with you in your carry-on baggage.
  • Slip-on shoes are a good footwear choice as you're less likely to be required to remove them when passing through security. Hiking boots and other bulky shoes are usually subjected to extra screening.
  • Avoid taking prohibited items in your carry-on bag. If you have any sharp objects like a pocket knife or tools, pack them safely away in your checked luggage. They won't be allowed on board and will be confiscated.

Book with confidence

If you love the thought of getting cozy in a town that fewer than one thousand people call home, pack your bags for Jamaica, VT. We’re talking about licking farm-fresh ice cream in a setting where a red town hall resembles a perfect dollhouse. Plan to do a little driving around to watch sheep herders live out all your old-fashioned fantasies. Next, dip into Jamaica State Park for extraordinary hiking and glimpses of the West River. Windham County’s local artisans will be happy to demonstrate glass blowing, weaving, and pottery for you, and local farmers and food artisans are more than ready to share fresh cheeses and wines with you. Additionally, the town’s great opportunities for golfing, skiing, snowboarding, fishing, and hiking will keep you satisfied through every season. Of course, the region's famous fall foliage is enough to make a single weekend change your life.

Now is a great time to crawl under your favourite Vermont-style crochet blanket and plan a very fun vacation with Expedia. Unlike Vermont’s famous maple syrup, you’ll actually want our low rates on flights to Jamaica Vermont to stick to your fingers.

Reserve the World's Cheapest Tickets Today

Save yourself the hassle of searching all over the Internet by grabbing discount deals on Expedia.ca today. You’ll find unbeatable prices on airfare simply by entering your travel dates and preferred departure airport into our travel tools right now. We’re connected with nearly every airline carrier offering flights to the Green Mountain State. Regardless of how many friends, family members, or kids you’re travelling with, we’ve got offers you’ll love.

Explore Great Airport Options

As part of our commitment to offering affordable and flexible flight options, we work with a wide variety of airports serving Windham County and the Brattleboro area. We want to give you freedom to choose to fly to nearly any airport in Vermont or New England that fits your travel itinerary.

Book Cheap Specials to the Brattleboro Area Today

The idea of an affordable vacation will take on a whole new meaning when you combine our cheap flights to Jamaica, VT with overnight accommodations. Whether you’re envisioning a smoky log cabin, a quaint bed and breakfast, or a roomy hotel room, we’ve got you covered. We just know that stepping outside your hotel door to the sights and smells of maples and white pines is sure to make you feel like a brand new person. Earn the right to take your place among prismatic leaves and rolling pastures by booking your vacation with Expedia today.

Travel information

Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Destination city name
Rutland
Roundtrip price
CA $621

Trending flights to Jamaica

Prices were available within the past 7 days and start at CA $352 for one-way flights and CA $622 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Fri, Nov 6 - Sun, Nov 8
YYZ
Toronto
RUT
Rutland
CA $622 Roundtrip, found 8 hours ago
CA $622
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Fri, Nov 6 from Toronto to Rutland, returning Sun, Nov 8, priced at CA $622 found 8 hours ago

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