Search Cheap Flights to
Pittsfield

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Pittsfield Flights as Low as $133

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Thu, Aug 28 - Sun, Aug 31
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$133 Roundtrip, found 1 day ago
$133
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Aug 28 from Raleigh - Durham Intl. to Albany Intl., returning Sun, Aug 31, priced at $133 found 1 day ago
American Airlines
Tue, Sep 16 - Wed, Sep 17
DCA
Ronald Reagan Washington National
ALB
Albany Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 16 from Ronald Reagan Washington National to Albany Intl., returning Wed, Sep 17, priced at $137 found 1 day ago
Breeze Airways
Thu, Aug 28 - Sun, Aug 31
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Aug 28 from Raleigh - Durham Intl. to Albany Intl., returning Sun, Aug 31, priced at $138 found 1 day ago
Breeze Airways
Thu, Aug 28 - Sun, Aug 31
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$143 Roundtrip, found 1 day ago
$143
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Aug 28 from Raleigh - Durham Intl. to Albany Intl., returning Sun, Aug 31, priced at $143 found 1 day ago
Breeze Airways
Sun, Aug 3 - Thu, Aug 7
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$149 Roundtrip, found 1 day ago
$149
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, Aug 3 from Raleigh - Durham Intl. to Albany Intl., returning Thu, Aug 7, priced at $149 found 1 day ago
Breeze Airways
Thu, Sep 4 - Tue, Sep 9
MCO
Orlando Intl.
ALB
Albany Intl.
$149 Roundtrip, just found
$149
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Sep 4 from Orlando Intl. to Albany Intl., returning Tue, Sep 9, priced at $149 just found
Breeze Airways
Sun, Aug 3 - Thu, Aug 7
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$154 Roundtrip, found 1 day ago
$154
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, Aug 3 from Raleigh - Durham Intl. to Albany Intl., returning Thu, Aug 7, priced at $154 found 1 day ago
Breeze Airways
Thu, Sep 4 - Tue, Sep 9
MCO
Orlando Intl.
ALB
Albany Intl.
$154 Roundtrip, just found
$154
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Sep 4 from Orlando Intl. to Albany Intl., returning Tue, Sep 9, priced at $154 just found
JetBlue Airways
Wed, Nov 5 - Tue, Nov 11
MCO
Orlando Intl.
ALB
Albany Intl.
$157 Roundtrip, found 4 hours ago
$157
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Wed, Nov 5 from Orlando Intl. to Albany Intl., returning Tue, Nov 11, priced at $157 found 4 hours ago
Breeze Airways
Sun, Aug 3 - Thu, Aug 7
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$159 Roundtrip, found 1 day ago
$159
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, Aug 3 from Raleigh - Durham Intl. to Albany Intl., returning Thu, Aug 7, priced at $159 found 1 day ago
JetBlue Airways
Wed, Sep 3 - Mon, Sep 8
MCO
Orlando Intl.
ALB
Albany Intl.
$160 Roundtrip, found 1 day ago
$160
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Sep 3 from Orlando Intl. to Albany Intl., returning Mon, Sep 8, priced at $160 found 1 day ago
Delta
Tue, Sep 16 - Wed, Sep 17
DCA
Ronald Reagan Washington National
ALB
Albany Intl.
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 16 from Ronald Reagan Washington National to Albany Intl., returning Wed, Sep 17, priced at $177 found 1 day ago
Bargain Flight
Mon, Aug 25 - Wed, Sep 3
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Mon, Aug 25 from Raleigh - Durham Intl. to Albany Intl., returning Wed, Sep 3, priced at $189 found 1 day ago
United
Tue, Aug 26 - Sat, Aug 30
SFO
San Francisco Intl.
ALB
Albany Intl.
$242 Roundtrip, found 1 day ago
$242
Roundtrip
found 1 day ago
Select United flight, departing Tue, Aug 26 from San Francisco Intl. to Albany Intl., returning Sat, Aug 30, priced at $242 found 1 day ago
Bargain Flight
Tue, Jul 8 - Wed, Jul 9
CLT
Charlotte-Douglas Intl.
ALB
Albany Intl.
$249 Roundtrip, found 1 day ago
$249
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Jul 8 from Charlotte-Douglas Intl. to Albany Intl., returning Wed, Jul 9, priced at $249 found 1 day ago
Alaska Airlines
Tue, Jul 15 - Wed, Jul 30
SFO
San Francisco Intl.
ALB
Albany Intl.
$698 Roundtrip, found 1 day ago
$698
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Jul 15 from San Francisco Intl. to Albany Intl., returning Wed, Jul 30, priced at $698 found 1 day ago

Cheap Flights to Pittsfield

Fall in love at first flight with your vacation to Pittsfield by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Pittsfield on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Pittsfield, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Pittsfield

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Pittsfield with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the ALB airport.

What is the cheapest month to fly to Pittsfield?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Pittsfield are in August, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Pittsfield?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 14 to choose from for your flight to Pittsfield.

What airport is best to fly into Pittsfield?

When you’re planning your trip to Pittsfield, convenience is the name of the game. Luckily, Pittsfield Pittsfield Municipal Airport is nearby so you can deplane and get going on checking off everything on your Pittsfield must-do list.

How much are flights to Pittsfield?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Pittsfield on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $133, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Pittsfield?

The trick to saving a stack of cash on your flight to Pittsfield? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $133 right now, why wait?

Pittsfield Flight Information
Destination airport
Albany Intl.
Destination airport IATA code
ALB
Roundtrip price
$619

Last Minute Hotel Deals in Pittsfield

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 ...
5.2/10 (737 reviews)
"Rooms were much nicer than expected. Despite the somewhat dated exterior and overall first impression from the outside, the rooms were solidly good, clean, and comfortable. Good value for the price."

Reviewed on Jul 1, 2025

Get rates
FairBridge Inn Express
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! (1,002 reviews)
"Excellent to stay. Bo couldnt have been nicer, getting us in early so we could attend a funeral. Only suggestion would be in the suites, a comfortable chair would be nice in the sitting area and a chair of any kind in the king area."

Reviewed on Jul 1, 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! (813 reviews)
"Clean rooms Staff was very friendly and helpful"

Reviewed on Jul 5, 2025

Get rates
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (502 reviews)
"Lovely place to stay … was only overnight for an event at Tanglewood but, the property would be a great place for a multi day stay with family. Great kitchen area and living room and good size bedroom and bathroom. Lots of common space in the lobby area for group gatherings. Great location"

Reviewed on Jul 4, 2025

Get rates
Berkshire Mountain Lodge
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! (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

Get rates
Hotel On North
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! (776 reviews)
Average motel, decent area, not worth $300 per nig
"Average motel with friendly staff. Clean room and bathroom. Needs a paint job (door to the room should be replaced) and some room maintenance . Definitely not worth $300 a night. The next night, I stayed at Hampton Inn for $200 a much nicer hotel with a free breakfast the next day."

Reviewed on Jul 6, 2025

Get rates
Berkshire Inn
Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield
3 out of 5
1032 South Street, Pittsfield, MA
Stay at this 3-star hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (634 reviews)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service."

Reviewed on Jun 16, 2025

Get rates
Hilton Garden Inn Lenox Pittsfield
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 ...
8.8/10 Excellent! (294 reviews)
Very pleased
"The unit was clean and very spacious with full kitchen and separate bedroom. The only negative was the hot temperature, and when we turned on the air conditioning, we didn't hear it turn on. We called for assistance and received immediate attention, learning that it takes a while for the cooling ..."

Reviewed on Jul 4, 2025

Get rates
The Central Downtown Inn & Suites
See all 1,347 properties in Pittsfield
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.