Cheap Flights to Pittsfield from $56

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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 $114 and $56 for one-way flights to Pittsfield for the period specified. Prices and availability are subject to change. Additional terms apply

Thu, Sep 4 - Thu, Sep 11
MCO
Orlando Intl.
ALB
Albany Intl.
$114 Roundtrip, found 2 hours ago
$114
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, Sep 4 from Orlando Intl. to Albany Intl., returning Thu, Sep 11, priced at $114 found 2 hours ago
OriginDestinationTravel DatesFlights From*
RSWLathamAugust 24 to August 28$145
JFKLathamAugust 9 to August 20$249
MANLathamOctober 7 to October 25$970
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKLathamJuly 27 to July 31$507
RSWLathamJuly 27 to August 7$562
*Prices include taxes and fees

Pittsfield Flight Information

Traveling to
Pittsfield
Lowest Price
$114
Number of Airlines Serving
Airlines Serving
Breeze Airways
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
$88 nightly
The price is $99 total per night from Jul 20 to Jul 21
$99 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! (1,013 reviews)
"Friendliness and cleanliness"

Reviewed on Jul 15, 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
$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 4-star guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum ...
8.6/10 Excellent! (298 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
$70 nightly
The price is $79 total per night from Jul 29 to Jul 30
$79 total
Jul 29 - Jul 30
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 (743 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 Aug 12 to Aug 13
$211 total
Aug 12 - Aug 13
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! (744 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
$135 nightly
The price is $151 total per night from Jul 28 to Jul 29
$151 total
Jul 28 - Jul 29
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! (822 reviews)
Very solid spot
"Great spot for exploring the area. Walking distance to downtown, and easy drive to nature, which is why I was in town w/ friends. Only complaint is that the hot water ran out really fast in the showers the days we were there"

Reviewed on Jul 16, 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
$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 4-star guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum ...
8.6/10 Excellent! (298 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
$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! (1,013 reviews)
"Friendliness and cleanliness"

Reviewed on Jul 15, 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 Aug 12 to Aug 13
$211 total
Aug 12 - Aug 13
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! (744 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! (1,013 reviews)
"Friendliness and cleanliness"

Reviewed on Jul 15, 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
$135 nightly
The price is $151 total per night from Jul 28 to Jul 29
$151 total
Jul 28 - Jul 29
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! (822 reviews)
Very solid spot
"Great spot for exploring the area. Walking distance to downtown, and easy drive to nature, which is why I was in town w/ friends. Only complaint is that the hot water ran out really fast in the showers the days we were there"

Reviewed on Jul 16, 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
$88 nightly
The price is $99 total per night from Jul 20 to Jul 21
$99 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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
per person
Sep 10 - Sep 14
found 3 hours ago
Roundtrip flight included
Cleveland (CLE) to Albany (ALB)
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
per person
Sep 10 - Sep 14
found 3 hours ago
Roundtrip flight included
Cleveland (CLE) to Albany (ALB)
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Need a Car For After Your Flight?

Compact SUV

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

$89

$238 total
found 1 day ago
Compact SUV undefined

Midsize SUV

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

$91

$243 total
found 1 day ago
Midsize SUV undefined

Standard SUV

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

$96

$256 total
found 1 day ago
Standard SUV undefined

Premium Pickup Regular Cab

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

$102

$272 total
found 1 day ago
Premium Pickup Regular Cab undefined

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.