Cheap Flights to Pittsfield from $58

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 Much Does it Cost To Fly To Pittsfield?

The cheapest prices found with in the last 7 days for return flights were $111 and $58 for one-way flights to Pittsfield for the period specified. Prices and availability are subject to change. Additional terms apply

Mon, Sep 22 - Mon, Sep 29
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$111 Roundtrip, found 1 day ago
$111
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Mon, Sep 22 from Raleigh - Durham Intl. to Albany Intl., returning Mon, Sep 29, priced at $111 found 1 day ago
OriginDestinationTravel DatesFlights From*
RSWLathamAugust 24 to August 28$152
JFKLathamSeptember 10 to September 11$253
MANLathamJune 26 to June 30$1,074
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RSWLathamJune 22 to July 3$455
MANLathamJune 21 to July 2$1,015
*Prices include taxes and fees

Pittsfield Flight Information

Traveling to
Pittsfield
Lowest Price
$111
Number of Airlines Serving
Airlines Serving
Avelo Airlines
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Amazing Pittsfield Accommodation Deals

Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St, Pittsfield, MA
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! (766 reviews)
"The motel was nicely done and clean. The beds were comfortable"

Reviewed on Jun 12, 2025

Get rates
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
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! (1,000 reviews)
"I liked this place. Staff couldn't be nicer and pretty good free breakfast. Please loves dogs too and some nice grassy areas in the back to walk them."

Reviewed on Jun 6, 2025

Get rates
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
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! (284 reviews)
"The suite we stayed in was beautiful, and it was available at a great price. It was clean, well maintained, and well furnished. I was very surprised at how big the space was. It was also in a great location in Pittsfield; it was very near to local theaters and restaurants. If it is available next ..."

Reviewed on Jun 8, 2025

Get rates
The Central Downtown Inn & Suites
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
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 ...
5.4/10 (723 reviews)
"Friendly staff and quick checkin"

Reviewed on Mar 8, 2025

Get rates
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
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! (736 reviews)
"Best place to stay in Pittsfield."

Reviewed on Jun 13, 2025

Get rates
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
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! (792 reviews)
"All was great, except parking was quiet of walk"

Reviewed on Jun 13, 2025

Get rates
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
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! (284 reviews)
"The suite we stayed in was beautiful, and it was available at a great price. It was clean, well maintained, and well furnished. I was very surprised at how big the space was. It was also in a great location in Pittsfield; it was very near to local theaters and restaurants. If it is available next ..."

Reviewed on Jun 8, 2025

Get rates
The Central Downtown Inn & Suites
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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
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! (1,000 reviews)
"I liked this place. Staff couldn't be nicer and pretty good free breakfast. Please loves dogs too and some nice grassy areas in the back to walk them."

Reviewed on Jun 6, 2025

Get rates
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
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! (736 reviews)
"Best place to stay in Pittsfield."

Reviewed on Jun 13, 2025

Get rates
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
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! (1,000 reviews)
"I liked this place. Staff couldn't be nicer and pretty good free breakfast. Please loves dogs too and some nice grassy areas in the back to walk them."

Reviewed on Jun 6, 2025

Get rates
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
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! (792 reviews)
"All was great, except parking was quiet of walk"

Reviewed on Jun 13, 2025

Get rates
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St, Pittsfield, MA
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! (766 reviews)
"The motel was nicely done and clean. The beds were comfortable"

Reviewed on Jun 12, 2025

Get rates
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.

Best Pittsfield Flight and Hotel Packages

Pittsfield flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
per person
Aug 12 - Aug 14
found 8 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
Park Manor Hotel

Park Manor Hotel

4 out of 5
per person
Jul 18 - Jul 20
found 6 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Albany (ALB)
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
per person
Aug 1 - Aug 3
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Don't see what you're looking for?
See all available trips from Dallas to Pittsfield
View all trips

Need a Car For After Your Flight?

Economy Special

  • 4 people
  • Unlimited mileage
Albany, New York, USA

$60

$120 total
found 20 hours ago
Economy Special undefined

Midsize SUV

  • 5 people
  • Unlimited mileage
Albany, New York, USA

$62

$124 total
found 20 hours ago
Midsize SUV undefined

Special

  • 5 people
  • Unlimited mileage
Albany, New York, USA

$62

$124 total
found 1 day ago
Special undefined

Compact

  • 5 people
  • Unlimited mileage
Albany, New York, USA

$62

$124 total
found 20 hours ago
Compact undefined
Lowest prices found within the past 20 hours. Prices and availability subject to change. Additional terms may apply.

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 35 mi 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.