Cheap Flights to The Berkshires , MA from CA $327

View CA $327 flight on Wed, Oct. 22, 2025Opens in a new window

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How much is the cheapest flight to The Berkshires?

Prices were available within the past 7 days and start at CA $327 for one-way flights and CA $548 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Sep. 6 - Thu, Sep. 18
YYZ
Toronto
BDL
Hartford
CA $548 Roundtrip, found 2 days ago
CA $548
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Sep. 6 from Toronto to Hartford, returning Thu, Sep. 18, priced at CA $548 found 2 days ago
American Airlines
Mon, Sep. 8 - Sat, Sep. 13
YYC
Calgary
BDL
Hartford
CA $564 Roundtrip, found 6 days ago
CA $564
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep. 8 from Calgary to Hartford, returning Sat, Sep. 13, priced at CA $564 found 6 days ago
JetBlue Airways
Sun, Nov. 2 - Tue, Nov. 18
YVR
Vancouver
BDL
Hartford
CA $570 Roundtrip, found 10 hours ago
CA $570
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Sun, Nov. 2 from Vancouver to Hartford, returning Tue, Nov. 18, priced at CA $570 found 10 hours ago
United
Tue, Sep. 23 - Tue, Sep. 30
YEG
Edmonton
BDL
Hartford
CA $583 Roundtrip, found 1 day ago
CA $583
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep. 23 from Edmonton to Hartford, returning Tue, Sep. 30, priced at CA $583 found 1 day ago
WestJet
Sat, Aug. 23 - Tue, Aug. 26
YEG
Edmonton
BDL
Hartford
CA $645 Roundtrip, found 5 days ago
CA $645
Roundtrip
found 5 days ago
Select WestJet flight, departing Sat, Aug. 23 from Edmonton to Hartford, returning Tue, Aug. 26, priced at CA $645 found 5 days ago

Expedia.ca gives you the best tools to secure great deals on flights to The Berkshires. 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 The Berkshires. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to The Berkshires.

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 The Berkshires 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 The Berkshires.

Looking to save even more? Get additional savings by bundling your The Berkshires 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 The Berkshires trip!

Frequently asked questions

How do I find cheap flights to The Berkshires that have flexible change policies?
At Expedia, we've been channeling our inner yogi to give you the most flexible fares around. Just check the "No change fee" box directly under the "Flexible change policies" subheading to find your ideal flight to The Berkshires.
Which airlines fly to The Berkshires?
Reserve your ticket with any of these popular airlines and look forward to new adventures in The Berkshires:

  • American Airlines - 889 flights to or near The Berkshires each month, including 546 flights to Bradley Intl. Airport (BDL) and 343 to Albany Intl. Airport (ALB) per month.
  • Southwest Airlines - 611 flights to or near The Berkshires each month, including 320 flights to Bradley Intl. Airport (BDL) and 290 to Albany Intl. Airport (ALB) per month.
  • Delta - 542 flights to or near The Berkshires each month, including 307 flights to Bradley Intl. Airport (BDL) and 234 to Albany Intl. Airport (ALB) per month.

How can I find cheap tickets to The Berkshires?
You'll always walk away with a fabulous deal with Expedia, but our "flexible dates" search function makes it even easier. Enter your preferred flight date, then click on the flexible dates link above to compare prices for nearby days. CA $548 was the cheapest price for a flight to The Berkshires in the last seven days.
How much is a flight to The Berkshires?
One-way flights taking off from Calgary (YYC) sold for just CA $327 in the last seven days. During this period, the price of a return air ticket to The Berkshires varied between CA $548 and CA $645. If you spot a deal, grab it fast — these fares don't hang around for long.
What are the most popular airports to fly into in The Berkshires?
Deciding on an airport comes down to factors including your airline, budget and where you plan to explore. Here are your choices in The Berkshires:

  • Bradley Intl. Airport (BDL) - 2,012 flights per month.
  • Albany Intl. Airport (ALB) - 1,258 flights per month.

When is the cheapest time to fly to The Berkshires?
Try to leave early on in the week to secure a bargain fare to The Berkshires. Tuesday is normally the most cost-effective day to fly, with Monday running a close second. Saturday typically has the costliest prices. This is because lots of people choose to kick off their getaway on a weekend.
How much is a plane ticket to The Berkshires?
Seats to The Berkshires ranged from CA $548 to CA $645 in the last seven days. Usually, the earlier you make a reservation, the better the deal.
What are the best things to do in The Berkshires?

  • With so many wonderful things to see and do in Williamstown, it's not surprising that most tourists start their The Berkshires trip in this buzzing city. Spend your first couple of days checking out big attractions like Williams College before discovering some of this city's lesser-known highlights.
  • When thinking about what type of clothes to take on your trip, keep in mind that Williamstown has a humid continental climate. For a clearer idea of what to expect while you're there, check the weather before you take off.
  • When you want to get out and see more of this beautiful region, grab the keys to one of our low-priced car rentals and make your way to Boston. It's approximately 177 kilometres to the east of Williamstown and also has renowned tourist sights, such as Salem Harbour.

What is the best time to go to The Berkshires?
Almost anytime! The Berkshires is brimming with exciting things to do and places to explore, including the buzzing city of Pittsfield. June, July and August are the busiest months here. Plan your visit for the beginning of summer on June 20 and enjoy the warmth and sunshine. Temperatures usually range from 14ºC to 25ºC during this time.
What months are the cheapest to book a flight to The Berkshires?
A great month to book budget flights to The Berkshires is February. Bear in mind that in the USA, an expensive time to reserve a seat is the busy month of December.
Flights to The Berkshires information
Destination airport
Albany Intl.
Destination airport IATA code
ALB
Destination city name
Albany
Roundtrip price
CA $447

Trending flights to The Berkshires

Prices were available within the past 7 days and start at CA $327 for one-way flights and CA $548 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Sep. 6 - Thu, Sep. 18
YYZ
Toronto
BDL
Hartford
CA $548 Roundtrip, found 2 days ago
CA $548
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Sep. 6 from Toronto to Hartford, returning Thu, Sep. 18, priced at CA $548 found 2 days ago
*Available to Expedia members.