Cheap Flight Deals to Pittsfield MA from CA $86

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How to find cheap flights to Pittsfield?

The cheapest prices found with in the last 7 days for return flights were CA $237 and CA $86 for one-way flights to Pittsfield for the period specified. Prices and availability are subject to change. Additional terms apply

Thu, Aug. 14 - Thu, Aug. 28
MCO
Orlando Intl.
ALB
Albany Intl.
CA $237 Roundtrip, found 3 days ago
CA $237
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Thu, Aug. 14 from Orlando Intl. to Albany Intl., returning Thu, Aug. 28, priced at CA $237 found 3 days ago
Tue, Aug. 26 - Wed, Aug. 27
YYZ
Pearson Intl.
ALB
Albany Intl.
CA $603 Roundtrip, found 4 days ago
CA $603
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Aug. 26 from Pearson Intl. to Albany Intl., returning Wed, Aug. 27, priced at CA $603 found 4 days ago

Your guide to flights to Pittsfield, MA

Breeze Airways, JetBlue Airways, American Airlines fly to Pittsfield, so use Travelocity to search, find, and compare some truly tempting deals from the 4 airlines—that way you can be sure you’ve found the best deal for you. A flight to Pittsfield MA currently costs between CA $237 and CA $603. Prices vary, but for the best fares, travel in September when prices are at their lowest.  

Top tips for finding cheap flights to Pittsfield  

The cheapest flight for a round trip to Pittsfield is currently CA $237. When you search for flights to Pittsfield, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Pittsfield for nearby days.  The cheapest month to travel to Pittsfield is August from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Pittsfield 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Pittsfield with Travelocity 

We have top deals on plane tickets even for last minute flights to Pittsfield, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Pittsfield for less. 

Find The Perfect Hotel For After Your Flight

Amazing Place to Stay After Flight to Pittsfield

Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St, Pittsfield, MA
The price is CA $117 per night from Jul 31 to Aug 1
CA $117
CA $131 total
Jul 31 - Aug 1
includes taxes & fees
Stay at this motel in Pittsfield. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.6/10 Good! (785 reviews)
"It was clean and recently refurbished. The pool was a nice relaxing asset after a long day. The continental breakfast was just coffee or tea."

Reviewed on Jul. 22, 2025

Berkshire Inn
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
The price is CA $186 per night from Aug 17 to Aug 18
CA $186
CA $207 total
Aug 17 - Aug 18
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,012 reviews)
"Very friendly girl at the check-in who moved us (essentially upgraded us) to a suite after our initial room smelled of lingering cigarette smoke. She was very patient about my paranoia over the pilot light/flame in the room's fireplace. Great experience."

Reviewed on Jul. 18, 2025

Best Western Plus Berkshire Hills Inn & Suites
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St., Pittsfield, MA
The price is CA $177 per night from Aug 5 to Aug 6
CA $177
CA $198 total
Aug 5 - Aug 6
includes taxes & fees
Stay at this 4-star guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum ...
8.6/10 Excellent! (299 reviews)
"Nice kitchen, a comfy couch, and clean space. Bathroom is small and toilet needed two flushes. Location is great, right in downtown Pittsfield. We appreciated the service since they brought us extra towels minutes after we asked."

Reviewed on Jul. 16, 2025

The Central Downtown Inn & Suites
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FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
The price is CA $98 per night from Jul 31 to Aug 1
CA $98
CA $109 total
Jul 31 - Aug 1
includes taxes & fees
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
5.2/10 (754 reviews)
"Perfect location for my journey. Safe and clean."

Reviewed on Jul. 20, 2025

FairBridge Inn Express
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Luxury Hotels in Pittsfield

Hotel On North

Hotel On North

3.5 out of 5
297 North Street, Pittsfield, MA
The price is CA $260 per night from Aug 3 to Aug 4
CA $260
CA $290 total
Aug 3 - Aug 4
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (746 reviews)
"The room was spacious, clean and charming."

Reviewed on Jul. 26, 2025

Hotel On North
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
The price is CA $177 per night from Aug 17 to Aug 18
CA $177
CA $198 total
Aug 17 - Aug 18
includes taxes & fees
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (838 reviews)
"Convenient for our trip"

Reviewed on Jul. 27, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St., Pittsfield, MA
The price is CA $177 per night from Aug 5 to Aug 6
CA $177
CA $198 total
Aug 5 - Aug 6
includes taxes & fees
Stay at this 4-star guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum ...
8.6/10 Excellent! (299 reviews)
"Nice kitchen, a comfy couch, and clean space. Bathroom is small and toilet needed two flushes. Location is great, right in downtown Pittsfield. We appreciated the service since they brought us extra towels minutes after we asked."

Reviewed on Jul. 16, 2025

The Central Downtown Inn & Suites
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Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
The price is CA $186 per night from Aug 17 to Aug 18
CA $186
CA $207 total
Aug 17 - Aug 18
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,012 reviews)
"Very friendly girl at the check-in who moved us (essentially upgraded us) to a suite after our initial room smelled of lingering cigarette smoke. She was very patient about my paranoia over the pilot light/flame in the room's fireplace. Great experience."

Reviewed on Jul. 18, 2025

Best Western Plus Berkshire Hills Inn & Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Pittsfield

Hotel On North

Hotel On North

3.5 out of 5
297 North Street, Pittsfield, MA
The price is CA $260 per night from Aug 3 to Aug 4
CA $260
CA $290 total
Aug 3 - Aug 4
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (746 reviews)
"The room was spacious, clean and charming."

Reviewed on Jul. 26, 2025

Hotel On North
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
The price is CA $186 per night from Aug 17 to Aug 18
CA $186
CA $207 total
Aug 17 - Aug 18
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,012 reviews)
"Very friendly girl at the check-in who moved us (essentially upgraded us) to a suite after our initial room smelled of lingering cigarette smoke. She was very patient about my paranoia over the pilot light/flame in the room's fireplace. Great experience."

Reviewed on Jul. 18, 2025

Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
The price is CA $177 per night from Aug 17 to Aug 18
CA $177
CA $198 total
Aug 17 - Aug 18
includes taxes & fees
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (838 reviews)
"Convenient for our trip"

Reviewed on Jul. 27, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St, Pittsfield, MA
The price is CA $117 per night from Jul 31 to Aug 1
CA $117
CA $131 total
Jul 31 - Aug 1
includes taxes & fees
Stay at this motel in Pittsfield. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.6/10 Good! (785 reviews)
"It was clean and recently refurbished. The pool was a nice relaxing asset after a long day. The continental breakfast was just coffee or tea."

Reviewed on Jul. 22, 2025

Berkshire Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Need a car after flight to Pittsfield?

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

Which airlines fly to Pittsfield?
When it comes to plane travel, everybody has different wants and preferences. With 7 airlines flying into Pittsfield, you're sure to find what you're after. Companies with great reviews include:

  • American Airlines
  • Delta Air Lines
  • United Airlines

What airport is best to fly into Pittsfield?
Pittsfield has just one airport, which makes booking your flight to the city straightforward. Albany Intl. Airport (ALB) is about 56 kilometers from the action downtown.
Where to stay in Pittsfield
Whether you're in Pittsfield on a family break, a solo adventure or something else entirely, we're confident you'll find the ideal place to hit the hay. Book with Travelocity and select from 153 accommodations within a short distance of the heart of town.There's no more suitable time to indulge yourself than when you're on vacation. Lock in a room at the Yankee Suites Extended Stay and enjoy a taste of the high life during your stay. Watching your budget? Don't worry, you won't be left in the cold. The Berkshire Inn will keep you and your bank balance happy.
Places to visit in Pittsfield
0 Want some more ideas? 0 But that's not all there is. 0
How to get through airport security fast when traveling to Pittsfield
Make your journey to Pittsfield a little easier by reading over these helpful tips and pointers:

  • Keep your boarding pass and passport somewhere accessible. They'll be the first things you'll be told to produce by airport security.
  • Wallets, belts and power banks must be placed in a tray for X-raying. If you enter the body scanner with any one of these items, you'll be turned around and requested to remove them.
  • Electronic goods such as laptops, phones and cameras will need to be put through the X-ray machine separately. Be sure they're easily accessible.
  • Toothpaste, lip balm and other toiletry items in liquid, gel or cream form need to be stored in containers no larger than 3.4 ounces (100 milliliters). They also need to fit in a 1-quart (1-liter) clear resealable bag.
  • Airport security staff may ask you to remove your shoes before entering the body scanner. Pick a pair that you can slip off easily. There's nothing more tiresome than having to do your laces up over and over again.
  • The list of prohibited items is forever updating. Read over your carrier's official website for what is not allowed on board their flights.

Plane Tickets To Pittsfield

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Pittsfield. Browse through our inventory to explore a wide range of cheap flights to Pittsfield to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Pittsfield as you anxiously await to exit the plane and explore what Pittsfield has to offer. Considering all the amazing local food and culture in Pittsfield, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Pittsfield to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Pittsfield without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Pittsfield with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Pittsfield today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.