Cheap Flights to Pittsfield from $59

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How Much Does it Cost To Fly To Pittsfield?

The cheapest prices found with in the last 7 days for return flights were $104 and $59 for one-way flights to Pittsfield for the period specified. Prices and availability are subject to change. Additional terms apply

Tue, Aug 12 - Tue, Aug 19
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$104 Roundtrip, found 4 days ago
$104
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Aug 12 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Tue, Aug 19, priced at $104 found 4 days ago
OriginDestinationTravel DatesFlights From*
RSWLathamAugust 17 to August 21$145
JFKLathamAugust 4 to August 13$251
MANLathamOctober 7 to October 25$982
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RSWLathamJuly 20 to July 24$403
JFKLathamJuly 19 to August 8$575
*Prices include taxes and fees

Pittsfield Flight Information

Traveling to
Pittsfield
Lowest Price
$104
Number of Airlines Serving
Airlines Serving
Breeze Airways, Southwest 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
$92 nightly
The price is $103 total per night from Jul 20 to Jul 21
$103 total
Jul 20 - Jul 21
Total includes taxes and 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! (777 reviews)
"You can tell they've updated main aspects of the rooms, which was nice but there were details that still needed it. Plus exterior needs updating too. But overall it was good, convenient location"

Reviewed on Jul 6, 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
$127 nightly
The price is $141 total per night from Jul 27 to Jul 28
$141 total
Jul 27 - Jul 28
Total includes taxes and 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)
"Great"

Reviewed on Jul 13, 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
$119 nightly
The price is $133 total per night from Jul 16 to Jul 17
$133 total
Jul 16 - Jul 17
Total includes taxes and fees
Stay at this 4-star guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum ...
8.8/10 Excellent! (297 reviews)
Good
"The room was adequate for a one night stay."

Reviewed on Jul 12, 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
$69 nightly
The price is $78 total per night from Aug 5 to Aug 6
$78 total
Aug 5 - Aug 6
Total includes taxes and 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 (739 reviews)
"Shampoo and toilet paper should have been In the room."

Reviewed on Jun 29, 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
$189 nightly
The price is $211 total per night from Jul 21 to Jul 22
$211 total
Jul 21 - Jul 22
Total includes taxes and 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! (743 reviews)
Beautiful, perfect hotel
"Wow, I loved this hotel! The room was amazing, the beds were great. Great service, great people. Beautiful design. I would definitely stay here again."

Reviewed on Jul 5, 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
$129 nightly
The price is $144 total per night from Jul 21 to Jul 22
$144 total
Jul 21 - Jul 22
Total includes taxes and 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! (821 reviews)
Comfy beds, chair, good closet, very clean
"Overnight stay while on a family visit. Comfortable room, good beds, great AC. Quiet as well."

Reviewed on Jul 13, 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
$119 nightly
The price is $133 total per night from Jul 16 to Jul 17
$133 total
Jul 16 - Jul 17
Total includes taxes and fees
Stay at this 4-star guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum ...
8.8/10 Excellent! (297 reviews)
Good
"The room was adequate for a one night stay."

Reviewed on Jul 12, 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
$127 nightly
The price is $141 total per night from Jul 27 to Jul 28
$141 total
Jul 27 - Jul 28
Total includes taxes and 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)
"Great"

Reviewed on Jul 13, 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
$189 nightly
The price is $211 total per night from Jul 21 to Jul 22
$211 total
Jul 21 - Jul 22
Total includes taxes and 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! (743 reviews)
Beautiful, perfect hotel
"Wow, I loved this hotel! The room was amazing, the beds were great. Great service, great people. Beautiful design. I would definitely stay here again."

Reviewed on Jul 5, 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
$127 nightly
The price is $141 total per night from Jul 27 to Jul 28
$141 total
Jul 27 - Jul 28
Total includes taxes and 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)
"Great"

Reviewed on Jul 13, 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
$129 nightly
The price is $144 total per night from Jul 21 to Jul 22
$144 total
Jul 21 - Jul 22
Total includes taxes and 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! (821 reviews)
Comfy beds, chair, good closet, very clean
"Overnight stay while on a family visit. Comfortable room, good beds, great AC. Quiet as well."

Reviewed on Jul 13, 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
$92 nightly
The price is $103 total per night from Jul 20 to Jul 21
$103 total
Jul 20 - Jul 21
Total includes taxes and 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! (777 reviews)
"You can tell they've updated main aspects of the rooms, which was nice but there were details that still needed it. Plus exterior needs updating too. But overall it was good, convenient location"

Reviewed on Jul 6, 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.

Best Pittsfield Flight and Hotel Packages

Pittsfield flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
per person
Aug 29 - Sep 1
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Albany (ALB)
The Dewey

The Dewey

3.5 out of 5
Save 100% on your flight
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
Don't see what you're looking for?
See all available trips from Los Angeles to Pittsfield
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Need a Car For After Your Flight?

Midsize Special

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

$65

$173 total
found 8 hours ago
Midsize Special undefined

Standard Elite Special

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

$68

$181 total
found 8 hours ago
Standard Elite Special undefined

Economy

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

$68

$180 total
found 8 hours ago
Economy undefined

Standard

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

$68

$181 total
found 8 hours ago
Standard undefined
Lowest prices found within the past 8 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.