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Pittsfield

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Pittsfield Flights as Low as $278

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

Delta
Sat, Feb 15 - Tue, Feb 18
ORD
O'Hare Intl.
ALB
Albany Intl.
$278 Roundtrip, found 4 days ago
$278
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Feb 15 from O'Hare Intl. to Albany Intl., returning Tue, Feb 18, priced at $278 found 4 days ago
Delta
Sun, Jan 19 - Sun, Jan 19
ORD
O'Hare Intl.
ALB
Albany Intl.
$280 Roundtrip, found 6 days ago
$280
Roundtrip
found 6 days ago
Select Delta flight, departing Sun, Jan 19 from O'Hare Intl. to Albany Intl., returning Sun, Jan 19, priced at $280 found 6 days ago
Delta
Wed, Jan 15 - Sun, Jan 19
ORD
O'Hare Intl.
ALB
Albany Intl.
$291 Roundtrip, found 6 days ago
$291
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 15 from O'Hare Intl. to Albany Intl., returning Sun, Jan 19, priced at $291 found 6 days ago
Delta
Mon, Jan 13 - Tue, Jan 21
ORD
O'Hare Intl.
ALB
Albany Intl.
$298 Roundtrip, found 6 days ago
$298
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Jan 13 from O'Hare Intl. to Albany Intl., returning Tue, Jan 21, priced at $298 found 6 days ago
Delta
Mon, Jan 13 - Sun, Jan 19
ORD
O'Hare Intl.
ALB
Albany Intl.
$300 Roundtrip, found 6 days ago
$300
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Jan 13 from O'Hare Intl. to Albany Intl., returning Sun, Jan 19, priced at $300 found 6 days ago
Delta
Sun, Feb 16 - Tue, Feb 18
ORD
O'Hare Intl.
ALB
Albany Intl.
$303 Roundtrip, found 4 days ago
$303
Roundtrip
found 4 days ago
Select Delta flight, departing Sun, Feb 16 from O'Hare Intl. to Albany Intl., returning Tue, Feb 18, priced at $303 found 4 days ago
American Airlines
Thu, Jan 16 - Mon, Jan 20
ORD
O'Hare Intl.
ALB
Albany Intl.
$304 Roundtrip, found 6 days ago
$304
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Jan 16 from O'Hare Intl. to Albany Intl., returning Mon, Jan 20, priced at $304 found 6 days ago
Delta
Wed, Jan 15 - Thu, Jan 23
ORD
O'Hare Intl.
ALB
Albany Intl.
$309 Roundtrip, found 6 days ago
$309
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 15 from O'Hare Intl. to Albany Intl., returning Thu, Jan 23, priced at $309 found 6 days ago
United
Thu, Jan 16 - Mon, Jan 20
ORD
O'Hare Intl.
ALB
Albany Intl.
$310 Roundtrip, found 6 days ago
$310
Roundtrip
found 6 days ago
Select United flight, departing Thu, Jan 16 from O'Hare Intl. to Albany Intl., returning Mon, Jan 20, priced at $310 found 6 days ago
American Airlines
Thu, Jan 16 - Mon, Jan 20
ORD
O'Hare Intl.
ALB
Albany Intl.
$311 Roundtrip, found 6 days ago
$311
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Jan 16 from O'Hare Intl. to Albany Intl., returning Mon, Jan 20, priced at $311 found 6 days ago
American Airlines
Thu, Jan 16 - Mon, Jan 20
ORD
O'Hare Intl.
ALB
Albany Intl.
$318 Roundtrip, found 6 days ago
$318
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Jan 16 from O'Hare Intl. to Albany Intl., returning Mon, Jan 20, priced at $318 found 6 days ago
American Airlines
Tue, Dec 24 - Tue, Dec 31
CLT
Charlotte-Douglas Intl.
ALB
Albany Intl.
$329 Roundtrip, found 19 hours ago
$329
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Tue, Dec 24 from Charlotte-Douglas Intl. to Albany Intl., returning Tue, Dec 31, priced at $329 found 19 hours ago
Delta
Sat, Jan 4 - Sat, Jan 11
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$330 Roundtrip, found 20 hours ago
$330
Roundtrip
found 20 hours ago
Select Delta flight, departing Sat, Jan 4 from Dallas-Fort Worth Intl. to Albany Intl., returning Sat, Jan 11, priced at $330 found 20 hours ago
Delta
Tue, Jan 14 - Wed, Jan 22
ICT
Wichita Dwight D. Eisenhower National
ALB
Albany Intl.
$336 Roundtrip, found 1 day ago
$336
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jan 14 from Wichita Dwight D. Eisenhower National to Albany Intl., returning Wed, Jan 22, priced at $336 found 1 day ago
Delta
Sat, Jan 4 - Sat, Jan 11
DAL
Love Field
ALB
Albany Intl.
$392 Roundtrip, found 20 hours ago
$392
Roundtrip
found 20 hours ago
Select Delta flight, departing Sat, Jan 4 from Love Field to Albany Intl., returning Sat, Jan 11, priced at $392 found 20 hours ago
American Airlines
Fri, Aug 1 - Sun, Aug 3
BNA
Nashville Intl.
ALB
Albany Intl.
$446 Roundtrip, found 10 hours ago
$446
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Fri, Aug 1 from Nashville Intl. to Albany Intl., returning Sun, Aug 3, priced at $446 found 10 hours 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 February, 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 16 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 $278, 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 $278 right now, why wait?

Pittsfield Flight Information
Destination airport
Albany Intl.
Destination airport IATA code
ALB
Roundtrip price
$339

Last Minute Hotel Deals in Pittsfield

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3 out of 5
One West Street, Pittsfield, MA
The price is $111 per night from Jan 5 to Jan 6
$111
includes taxes & fees
Jan 5 - Jan 6, 2025
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! (701 reviews)
"Staff was very accommodating. The pool area was quite nice and it was deep"

Reviewed on Dec 16, 2024

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
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
The price is $105 per night from Jan 5 to Jan 6
$105
includes taxes & fees
Jan 5 - Jan 6, 2025
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)
"The bed was comfortable and room was nice."

Reviewed on Dec 10, 2024

Best Western Plus Berkshire Hills Inn & Suites
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
The price is $204 per night from Jan 1 to Jan 2
$204
includes taxes & fees
Jan 1 - Jan 2, 2025
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! (417 reviews)
"Good"

Reviewed on Dec 21, 2024

Berkshire Mountain Lodge
Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield
3 out of 5
1032 South Street, Pittsfield, MA
The price is $162 per night from Dec 31 to Jan 1
$162
includes taxes & fees
Dec 31 - Jan 1, 2025
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! (619 reviews)
"Check in and check out where quick and easy. The room was comfortable and clean. The staff were nice and accommodating. Central location to surrounding attractions."

Reviewed on Nov 10, 2024

Hilton Garden Inn Lenox Pittsfield
Berkshire Inn
Berkshire Inn
2 out of 5
150 W Housatonic St, Pittsfield, MA
The price is $96 per night from Dec 24 to Dec 25
$96
includes taxes & fees
Dec 24 - Dec 25
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! (751 reviews)
Nice Motel, No Breakfast
"This is a nice motel, though there is no continental breakfast. There is a pot of coffee made at 7am. The rooms are clean and updated, the mattress is good, airconditioner in back wall, simple round thermostat for hot water radiator heating, mini-fridge is compressor type, microwave."

Reviewed on Nov 27, 2024

Berkshire Inn
Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
The price is $144 per night from Dec 24 to Dec 25
$144
includes taxes & fees
Dec 24 - Dec 25
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,000 reviews)
"Stayed for a weekend wedding and it was a great location. Room was large"

Reviewed on Dec 19, 2024

Hotel Downstreet
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
The price is $108 per night from Jan 1 to Jan 2
$108
includes taxes & fees
Jan 1 - Jan 2, 2025
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,001 reviews)
"This hotel was awesome! We enjoyed the hot tub along with the fireplace in our room!"

Reviewed on Dec 15, 2024

The Yankee, Trademark Collection by Wyndham
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is $99 per night from Jan 5 to Jan 6
$99
includes taxes & fees
Jan 5 - Jan 6, 2025
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (455 reviews)
"The coziest best hotel in area! Staff was so wonderful, room was perfect! Lobby bar and lounge is so great."

Reviewed on Dec 19, 2024

Life House Berkshires
See all 1,266 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.