Cheap Flight Deals to Pittsfield MA from CA $146
Wander Wisely with exceptional service, 24/7 supportOpens in a new window
Feel at ease with free flight cancellations within 24 hours of booking
Change your flight without a fee on select flights
How to find cheap flights to Pittsfield?
The cheapest prices found with in the last 7 days for return flights were CA $441 and CA $146 for one-way flights to Pittsfield for the period specified. Prices and availability are subject to change. Additional terms apply
Your guide to flights to Pittsfield, MA
JetBlue Airways, Delta 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 $441 and CA $508. Prices vary, but for the best fares, travel in May 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 $441. 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 June 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
Great stay
Reviewed on Mar 30, 2026
Best Western Plus Berkshire Hills Inn & Suites
Staff was very accommodating. Room was ok but toilet didn’t flush without the water constantly running. Shower gel, shampoo & condition bottles were all empty in the shower. Had to call for new ones.
Reviewed on Mar 24, 2026
The Central Downtown Inn & Suites
Did not send check-in info via text, when I called they said they sent but never and resent, then gave me the wrong room. I booked double bed but got 1 king bed said double bed booking is not guaranteed and the rooms are sold out. However the worse part is the room is full of smoke smell so badly ...
Reviewed on Feb 21, 2026
FairBridge Inn Express
Luxury Hotels in Pittsfield
Hotel On North
Very clean room, friendly staff, and a feeling of being in a “fancy” hotel while still being within budget. The location was great - I enjoyed walking around and felt safe after dark. Easy walking distance from the Colonial Theater.
Reviewed on Mar 28, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
OK, the hotel needs updating, but the staff was so friendly and helpful it didn't even matter. We parked our car, walked everywhere, 2 min to the Colonial theater! Insider tip, if you buy a breakfast tix from the front desk it's less $ than paying at the restaurant.
Reviewed on Mar 29, 2026
The Central Downtown Inn & Suites
Did not send check-in info via text, when I called they said they sent but never and resent, then gave me the wrong room. I booked double bed but got 1 king bed said double bed booking is not guaranteed and the rooms are sold out. However the worse part is the room is full of smoke smell so badly ...
Reviewed on Feb 21, 2026
Best Western Plus Berkshire Hills Inn & Suites
Staff was very accommodating. Room was ok but toilet didn’t flush without the water constantly running. Shower gel, shampoo & condition bottles were all empty in the shower. Had to call for new ones.
Reviewed on Mar 24, 2026
Family Friendly Hotels in Pittsfield
Hotel On North
Very clean room, friendly staff, and a feeling of being in a “fancy” hotel while still being within budget. The location was great - I enjoyed walking around and felt safe after dark. Easy walking distance from the Colonial Theater.
Reviewed on Mar 28, 2026
Best Western Plus Berkshire Hills Inn & Suites
Staff was very accommodating. Room was ok but toilet didn’t flush without the water constantly running. Shower gel, shampoo & condition bottles were all empty in the shower. Had to call for new ones.
Reviewed on Mar 24, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
OK, the hotel needs updating, but the staff was so friendly and helpful it didn't even matter. We parked our car, walked everywhere, 2 min to the Colonial theater! Insider tip, if you buy a breakfast tix from the front desk it's less $ than paying at the restaurant.
Reviewed on Mar 29, 2026
Berkshire Inn
Great stay
Reviewed on Mar 30, 2026
Best Pittsfield Flight and Hotel Packages
Pittsfield flight + hotel packages - economy flights
Need a car after flight to Pittsfield?
Economy
Compact
Midsize
SUV
Frequently asked questions
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!
Need more than a Flight to Pittsfield?
Explore More Ways to Travel with Travelocity
- 4 Star Hotels in The Berkshires
- Agawam Hotels
- Cabins in Amherst
- Amherst Hotels
- Hotels near Berkshire Athenaeum
- Bernardston Hotels
- Blandford Hotels
- Buckland Hotels
- Cabins in Chicopee
- Chicopee Hotels
- Conway Hotels
- Dalton Hotels
- Drury Hotels
- Hotels near Eastern States Exposition
- Easthampton Hotels
- Florence Hotels
- Granville Hotels
- Golf Resorts & in Great Barrington
- Great Barrington Hotels
- Vacation Homes in Great Barrington
- Hadley Hotels
- Cabins in Holyoke
- Historic Hotels in Holyoke
- Hotels with Hot Tubs in Holyoke
- Pet Friendly Hotels in Holyoke
- Holyoke Hotels
- Hotels near Holyoke Mall
- Cottages in Lee
- Cottages in Lenox
- Lenox Hotels
- Longmeadow Hotels
- Monterey Hotels
- Hotels near Mount Greylock
- Hotels near National Shrine of the Divine Mercy
- New Marlborough Hotels
- Northampton Hotels
- Northfield Hotels
- Richmond Hotels
- Hotels near Six Flags New England
- South Egremont Hotels
- South Hadley Hotels
- Southampton Hotels
- Cottages in Southwick
- Pet Friendly Hotels in Springfield
- Springfield Hotels
- Stockbridge Hotels
- Hotels near Tanglewood Music Center
- Apartments in The Berkshires
- B&B in The Berkshires
- Cabins in The Berkshires
- Condos in The Berkshires
- Cottages in The Berkshires
- Luxury Hotels in The Berkshires
- Romantic Getaways & Hotels in The Berkshires
- Ski Resorts and in The Berkshires
- Spa Resorts & in The Berkshires
- Lodges in The Berkshires
- West Springfield Hotels
- Cabins in Western Massachusetts
- Westfield Hotels
- Williamstown Hotels
- Ace New Zealand Rental Cars in North Adams
- Avis Rental Cars in Otis
- Car rental Adams
- Car rental Lee
- Discount Car Rentals Rental Cars in Holyoke
- Drive on Holidays Rental Cars in Southwick
- First Car Rental Rental Cars in Becket
- First Car Rental Rental Cars in Southwick
- Global Rent a Car Rental Cars in North Adams
- Island Car Rentals Rental Cars in Adams
- Island Car Rentals Rental Cars in Easthampton
- Island Car Rentals Rental Cars in Otis
- Island Car Rentals Rental Cars in Southwick
- Island Car Rentals Rental Cars in Williamstown
- Maggiore Rental Cars in North Adams
- Mex Rent A Car Rental Cars in Northampton
- Ok Mobility Rental Cars in Northampton
- Right-Cars Rental Cars in Hatfield
- Right-Cars Rental Cars in Western Massachusetts
- Sicily By Car Rental Cars in Northampton
- Surprice Car Rentals Rental Cars in East Longmeadow