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Pittsfield

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Pittsfield Flights as Low as $249

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

American Airlines
Tue, Sep 8 - Sat, Sep 19
DCA
Ronald Reagan Washington National
ALB
Albany Intl.
$249 Roundtrip, found 13 hours ago
$249
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Tue, Sep 8 from Ronald Reagan Washington National to Albany Intl., returning Sat, Sep 19, priced at $249 found 13 hours ago
American Airlines
Mon, Jul 27 - Wed, Aug 5
DCA
Ronald Reagan Washington National
ALB
Albany Intl.
$255 Roundtrip, found 13 hours ago
$255
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Mon, Jul 27 from Ronald Reagan Washington National to Albany Intl., returning Wed, Aug 5, priced at $255 found 13 hours ago
American Airlines
Tue, Sep 8 - Sat, Sep 19
DCA
Ronald Reagan Washington National
ALB
Albany Intl.
$259 Roundtrip, found 13 hours ago
$259
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Tue, Sep 8 from Ronald Reagan Washington National to Albany Intl., returning Sat, Sep 19, priced at $259 found 13 hours ago
American Airlines
Mon, Jul 27 - Wed, Aug 5
DCA
Ronald Reagan Washington National
ALB
Albany Intl.
$265 Roundtrip, found 13 hours ago
$265
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Mon, Jul 27 from Ronald Reagan Washington National to Albany Intl., returning Wed, Aug 5, priced at $265 found 13 hours ago
Delta
Tue, Sep 8 - Sat, Sep 19
DCA
Ronald Reagan Washington National
ALB
Albany Intl.
$269 Roundtrip, found 13 hours ago
$269
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Sep 8 from Ronald Reagan Washington National to Albany Intl., returning Sat, Sep 19, priced at $269 found 13 hours ago
Delta
Fri, Jul 31 - Tue, Aug 4
DCA
Ronald Reagan Washington National
ALB
Albany Intl.
$275 Roundtrip, found 13 hours ago
$275
Roundtrip
found 13 hours ago
Select Delta flight, departing Fri, Jul 31 from Ronald Reagan Washington National to Albany Intl., returning Tue, Aug 4, priced at $275 found 13 hours ago
Delta
Tue, Sep 8 - Sat, Sep 19
DCA
Ronald Reagan Washington National
ALB
Albany Intl.
$284 Roundtrip, found 13 hours ago
$284
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Sep 8 from Ronald Reagan Washington National to Albany Intl., returning Sat, Sep 19, priced at $284 found 13 hours ago
American Airlines
Tue, Sep 8 - Sat, Sep 19
DCA
Ronald Reagan Washington National
ALB
Albany Intl.
$294 Roundtrip, found 13 hours ago
$294
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Tue, Sep 8 from Ronald Reagan Washington National to Albany Intl., returning Sat, Sep 19, priced at $294 found 13 hours ago
American Airlines
Mon, Jul 27 - Wed, Aug 5
DCA
Ronald Reagan Washington National
ALB
Albany Intl.
$301 Roundtrip, found 13 hours ago
$301
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Mon, Jul 27 from Ronald Reagan Washington National to Albany Intl., returning Wed, Aug 5, priced at $301 found 13 hours ago
American Airlines
Fri, Jul 31 - Tue, Aug 4
DCA
Ronald Reagan Washington National
ALB
Albany Intl.
$301 Roundtrip, found 13 hours ago
$301
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Fri, Jul 31 from Ronald Reagan Washington National to Albany Intl., returning Tue, Aug 4, priced at $301 found 13 hours ago
JetBlue Airways
Mon, Sep 7 - Tue, Sep 8
DCA
Ronald Reagan Washington National
ALB
Albany Intl.
$307 Roundtrip, found 4 days ago
$307
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Mon, Sep 7 from Ronald Reagan Washington National to Albany Intl., returning Tue, Sep 8, priced at $307 found 4 days ago
Bargain Flight
Tue, Sep 8 - Fri, Sep 11
DCA
Ronald Reagan Washington National
ALB
Albany Intl.
$357 Roundtrip, found 13 hours ago
$357
Roundtrip
found 13 hours ago
Select Bargain Flight flight, departing Tue, Sep 8 from Ronald Reagan Washington National to Albany Intl., returning Fri, Sep 11, priced at $357 found 13 hours ago
JetBlue Airways
Mon, Aug 10 - Tue, Aug 11
BWI
Baltimore Washington Intl. Thurgood Marshall
ALB
Albany Intl.
$402 Roundtrip, found 1 day ago
$402
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Aug 10 from Baltimore Washington Intl. Thurgood Marshall to Albany Intl., returning Tue, Aug 11, priced at $402 found 1 day ago
Delta
Mon, Aug 24 - Tue, Sep 1
DAL
Love Field
ALB
Albany Intl.
$485 Roundtrip, found 13 hours ago
$485
Roundtrip
found 13 hours ago
Select Delta flight, departing Mon, Aug 24 from Love Field to Albany Intl., returning Tue, Sep 1, priced at $485 found 13 hours ago
American Airlines
Tue, Jul 21 - Sat, Jul 25
MAF
Midland Intl.
ALB
Albany Intl.
$517 Roundtrip, found 1 day ago
$517
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jul 21 from Midland Intl. to Albany Intl., returning Sat, Jul 25, priced at $517 found 1 day ago
United
Wed, Jul 1 - Wed, Jul 1
IND
Indianapolis Intl.
ALB
Albany Intl.
$579 Roundtrip, found 13 hours ago
$579
Roundtrip
found 13 hours ago
Select United flight, departing Wed, Jul 1 from Indianapolis Intl. to Albany Intl., returning Wed, Jul 1, priced at $579 found 13 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 September, 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 $249, 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 $249 right now, why wait?

Pittsfield Flight Information
Destination airport
Albany Intl.
Destination airport IATA code
ALB
Roundtrip price
$134

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! (999 reviews)
"We thoroughly enjoyed our stay. The rooms are spacious and beautifully furnished, and having a stove and refrigerator along with a separate living/dining room was a definite plus. The 24/7 coffee and hot chocolate machine in the lobby was another perk, as were the hot tub and large (albeit shallow) ..."

Reviewed on Jun 24, 2026

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

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

2.5 out of 5
1055 South Street Pittsfield MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and ...
9.4/10 Exceptional! (115 reviews)
"Best hotel breakfast I have had in a long time. The breakfast attendant kept items well stocked. She made sure that vacated tables were cleaned and ready for the next guests to enjoy their meal. The room was kept very clean. I really enjoyed the fresh pancakes that were made to order by a pancake ..."

Reviewed on Jun 26, 2026

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Holiday Inn Express & Suites Pittsfield-Lenox-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 ...
9.6/10 Exceptional! (869 reviews)
"Always a great experience at Hotel on North! Great, comfortable room with amazing bathroom. Helpful and friendly staff. Safe parking in the rear secured lot."

Reviewed on Jun 24, 2026

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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 ...
8.6/10 Excellent! (1,000 reviews)
"Biggest issue was breakfast. Short staffed so several things were empty and not refilled why we were there."

Reviewed on Jun 25, 2026

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Best Western Plus Berkshire Hills Inn & Suites
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 ...
5.4/10 (831 reviews)
"Friendly staff and quiet"

Reviewed on Jun 19, 2026

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FairBridge Inn Express
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! (1,002 reviews)
"The hotel is getting a new parking garage so parking was at a premium. But the FREE valet service makes it worthwhile for sure. The rooms were extremely clean, comfortable and quiet. The buffet breakfast in the morning is top-notch and everyone I spoke to was very helpful accommodating, and truly ..."

Reviewed on Jun 25, 2026

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Holiday Inn & Suites Pittsfield-Berkshires by IHG
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. ...
7.8/10 Good! (866 reviews)
"Excelente lugar , privacidad para poder descansar"

Reviewed on Jun 23, 2026

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Berkshire Inn
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! (370 reviews)
"We arrived at 10 pm and the room had a broken AC and no sheets for pullout. The temperature was 95 degrees and the windows were left open suggesting that this was not a new problem. I had to contact the front desk (offsite) to request assistance. No one showed up after waiting for 45 minutes. We ..."

Reviewed on Jun 10, 2026

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The Central Downtown Inn & Suites
See all 1,337 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.