Cheap Flights to Winchester , MA from CA $190

View CA $190 flight on Wed, Dec. 3, 2025Opens in a new window

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How much is the cheapest flight to Winchester?

Prices were available within the past 7 days and start at CA $190 for one-way flights and CA $319 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Tue, Sep. 16 - Fri, Oct. 3
YTZ
Toronto
BOS
Boston
CA $319 Roundtrip, found 2 days ago
CA $319
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Tue, Sep. 16 from Toronto to Boston, returning Fri, Oct. 3, priced at CA $319 found 2 days ago
Air Canada
Wed, Dec. 3 - Thu, Jan. 22
YTZ
Toronto
BOS
Boston
CA $319 Roundtrip, just found
CA $319
Roundtrip
just found
Select Air Canada flight, departing Wed, Dec. 3 from Toronto to Boston, returning Thu, Jan. 22, priced at CA $319 just found
Delta
Thu, Dec. 18 - Tue, Jan. 6
YYZ
Toronto
BOS
Boston
CA $336 Roundtrip, found 4 hours ago
CA $336
Roundtrip
found 4 hours ago
Select Delta flight, departing Thu, Dec. 18 from Toronto to Boston, returning Tue, Jan. 6, priced at CA $336 found 4 hours ago
United
Sat, Sep. 6 - Sat, Sep. 13
YYZ
Toronto
BOS
Boston
CA $336 Roundtrip, just found
CA $336
Roundtrip
just found
Select United flight, departing Sat, Sep. 6 from Toronto to Boston, returning Sat, Sep. 13, priced at CA $336 just found
Air Transat
Fri, Oct. 3 - Mon, Oct. 6
YTZ
Toronto
BOS
Boston
CA $361 Roundtrip, just found
CA $361
Roundtrip
just found
Select Air Transat flight, departing Fri, Oct. 3 from Toronto to Boston, returning Mon, Oct. 6, priced at CA $361 just found

Find the cheapest month to fly from Columbus (CMH) to Boston (BOS)

September is typically the cheapest month to fly

From CA $118 - CA $222 per traveller.

Graph displaying average flight prices per month

Expedia.ca gives you the best tools to secure great deals on flights to Winchester. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Winchester. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Winchester.

Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Winchester flights with full confidence knowing that you've found the best deal online.

Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Winchester.

Looking to save even more? Get additional savings by bundling your Winchester flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Winchester trip!

Frequently asked questions

What is the name of Winchester's airport?
Logan Intl. Airport (BOS) is the only airport in Winchester.
How far is Logan Intl. Airport (BOS) from central Winchester?
Logan Intl. Airport is 14 kilometres from central Winchester, so expect a bit of a commute into the heart of the city.
What airport is best to fly into Winchester?
A flight to Winchester means hitting the tarmac at BOS. Disembark the plane, grab your bags and you'll be 14 kilometres from the centre of town.
How many airlines fly to Winchester?
There are a total of 43 airlines connecting Winchester with 121 airports from all over the globe.
Which airlines fly to Winchester?
Typically, travellers choose to fly with Delta, JetBlue and American Airlines when heading off to Winchester. The largest number of these flights come from New York, with Delta servicing this route the most.
How many nonstop flights are there to Winchester?
With around 3,070 nonstop flights each week, you'll be hitting the runway in Winchester before you can say, "Are we there yet?"
Where are the most popular flights to Winchester departing from?
Travellers frequently jet off from New York, Washington and Chicago airports when going to Winchester.
How long is the flight to Winchester Airport?
Which airport you depart from determines how much of the in-flight entertainment you'll get to enjoy. From New York to Winchester, the average flight time is 1 hour and 19 minutes. From Washington it's around 1 hour and 36 minutes, and from Chicago it's 2 hours and 20 minutes.
How to book the cheapest flight to Winchester?
We've all come across those jet-setters who somehow get impossibly cheap airfares every time they fly. Would you like to know how to do it for your Winchester vacation? Don't leave it until the last possible moment to lock in your flight. Another terrific way to grab the most competitive fare is to shop around. If where you're headed has more than one airport, don't forget to research the cost of flying into a less busy terminal. Last but not least, be ready to book quickly if you find a real bargain. It might not stick around for too long! With a bit of knowledge and some good fortune, the perfect airfare can be yours.
Do you have any tips for my flight to Winchester?
Depending on where you're coming from, your journey to Winchester could be completely stress-free or it could drag on forever. We've put together some handy travel tips that will help you start your next unforgettable escape on a positive note. What to pack in your hand luggage:

  • Air travel can be a stress-free experience if you take the right gear. First of all you'll need basic toiletry items, such as a toothbrush and lip balm, a spare pair of socks and something to read. Next, find room in your bag for your phone, tablet and chargers, your medications and perhaps a blow-up neck pillow too. Last, but definitely not least, don't forget to take your passport, travel docs and some money.

Do not pack the following items in your hand luggage:

  • While the list of restricted items differs between air carriers, the general rule to follow is avoid carrying anything sharp, flammable or explosive. This includes things like tools, metal cutlery, fuels and bleaching agents. Sports equipment like golf clubs, and objects that could harm passengers, such as firearms and swords, can't come on board with you either.

What to wear on a flight:

  • Go for comfort over style. Prepare for changes in cabin temperature by layering up, and wear easy-to-remove shoes like sneakers.
  • Caused by sustained periods of immobility, deep vein thrombosis (DVT) is a blood clot condition that can affect some passengers during long-haul flights. Lower your risks by drinking water, keeping your legs and feet moving and wearing compression socks or tights.

How to get through airport security fast when flying to Winchester?
It's all about being organized. We've rounded up some tips and tricks for a fuss-free trip through airport security. Look out Winchester, here you come:

  • Airport security personnel first need to check that you have a valid passport and matching boarding pass before you're allowed to proceed any further. Have them within easy reach, ready for inspection.
  • The X-ray machine comes next. Remove anything on you that is likely to set off the alarm. This includes items like earphones or headphones, as well as your coat or jacket. They'll all need to go on the X-ray conveyor belt.
  • All your electronic gadgets, including your phone and tablet, are also required to be scanned.
  • Any liquids or gels, such as perfume or hand cream, that you want to take on board need to be in containers no greater than 3.4 ounces (100 millilitres). Also, they all must fit inside a quart-size (one litre), clear zip-lock bag.
  • Slip-on shoes are a sensible footwear choice as you're less likely to be asked to remove them when going through security. Big boots and heavier-style shoes are often subjected to additional screening.
  • Sharp or pointed items can't be taken on board. They'll be seized at security, so pack them safely away in your checked suitcase.

Flights to Winchester information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Destination city name
Boston
Roundtrip price
CA $318

Trending flights to Winchester

Prices were available within the past 7 days and start at CA $190 for one-way flights and CA $319 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Tue, Sep. 16 - Fri, Oct. 3
YTZ
Toronto
BOS
Boston
CA $319 Roundtrip, found 2 days ago
CA $319
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Tue, Sep. 16 from Toronto to Boston, returning Fri, Oct. 3, priced at CA $319 found 2 days ago
*Available to Expedia members.