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 $156

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

JetBlue Airways
JetBlue Airways
JetBlue Airways
American Airlines
JetBlue Airways
American Airlines
JetBlue Airways
American Airlines
Delta
United
Delta
American Airlines
Bargain Flight
American Airlines
American Airlines
Alaska Airlines

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 March, 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 15 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 $156, 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 $156 right now, why wait?

Pittsfield Flight Information
Destination airport
Pittsfield
Destination airport IATA code
ALB

Last Minute Hotel Deals in Pittsfield

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (835 reviews)
We enjoyed our stay. Hotel is a little out dated but the rooms are a generous size at low prices. Pool was huge and as a lap swimmer this was fantastic. Checkout is early at 10:00. That is really the only complaint. Staff is very nice

Reviewed on Feb 8, 2026

Berkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (1,001 reviews)
Rooms were clean and spacious. Our room had 2 queen beds and they easily accommodated 2 of us and our late teen children. It's only 20 minutes from Jiminy Peak skiing area. There are several breakfast and food places nearby.

Reviewed on Feb 2, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Book a stay at this 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! (823 reviews)
Room was spotless, staff was amazing! Loved the bathroom setup! Will recommend and stay again!

Reviewed on Feb 9, 2026

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! (1,001 reviews)
Great place, room was clean and spacious. Breakfast time could last a little longer though, ending time was 9:30am, maybe extending until 11am is best. But overall was great.

Reviewed on Jan 20, 2026

Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Stay at this hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Guido's Marketplace and Herman Melville's Arrowhead ...
9.2/10 Wonderful! (82 reviews)
Amazing stuff they went above and beyond to accommodate on fridge cold day, good breakfast, hot tub is amazing

Reviewed on Feb 8, 2026

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3 out of 5
1032 South Street Pittsfield MA
Stay at this hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
9.2/10 Wonderful! (666 reviews)
👍

Reviewed on Jan 26, 2026

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 guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum are located ...
8.6/10 Excellent! (355 reviews)
Checked in was easy, instructions were easy to follow. Only one staff member but he was very responsive to issues/concern. We booked 2 rooms but one room was on another building and it was outdated. Rooms were cleaned but there was this musty smell on the hallway. Overall, good stay, close to 2 ski ...

Reviewed on Feb 2, 2026

The Central Downtown Inn & Suites
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! (840 reviews)
The room is good, it’s clean. However need more lighting in room, except for bathroom are so super clean and beautiful setting!! Bed is very comfortable to sleep, easily to sleep quickly. I would come back again when I use this place.

Reviewed on Dec 3, 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.