Cheap Flights to Western Massachusetts from $35

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How Much Does it Cost To Fly To Western Massachusetts?

The cheapest prices found with in the last 7 days for return flights were $84 and $35 for one-way flights to Western Massachusetts for the period specified. Prices and availability are subject to change. Additional terms apply

Fri, Oct 17 - Mon, Oct 20
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$84 Roundtrip, just found
$84
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Oct 17 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Oct 20, priced at $84 just found
Sat, Oct 11 - Mon, Oct 20
MCO
Orlando Intl.
BDL
Bradley Intl.
$99 Roundtrip, found 2 days ago
$99
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Oct 11 from Orlando Intl. to Bradley Intl., returning Mon, Oct 20, priced at $99 found 2 days ago
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksOctober 2 to October 6$97
RSWWorcesterDecember 5 to December 15$123
RSWLathamDecember 3 to December 13$142
RSWWindsor LocksDecember 4 to December 10$147
JFKWorcesterDecember 3 to December 8$229
JFKLathamOctober 23 to October 29$238
MANWindsor LocksOctober 1 to October 9$719
MANLathamSeptember 29 to October 13$888
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKWindsor LocksSeptember 26 to September 28$98
RSWWindsor LocksSeptember 26 to October 8$210
JFKWorcesterSeptember 27 to September 28$499
*Prices include taxes and fees

Western Massachusetts BDL Flight Information

Traveling to
Western Massachusetts BDL
Lowest Price
$84
Number of Airlines Serving
0
Airlines Serving
Spirit Airlines, Breeze Airways
Number of Daily Flights
1
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Amazing Western Massachusetts Accommodation Deals

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2 out of 5
42 Stockbridge Rd, West Stockbridge, MA
$66 nightly
The price is $73 total per night from Sep 23 to Sep 24
$73 total
Sep 23 - Sep 24
Total with taxes and fees
Stay at this motel in West Stockbridge. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.6/10 (1,002 reviews)
"Very nice staff!!"

Reviewed on Aug 29, 2025

Opens in a new windowPleasant Valley Motel West Stockbridge
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 out of 5
1254 Riverdale Street, West Springfield, MA
$89 nightly
The price is $102 total per night from Oct 1 to Oct 2
$102 total
Oct 1 - Oct 2
Total with taxes and fees
Stay at this hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (1,009 reviews)
"Excellent overall!"

Reviewed on Sep 13, 2025

Opens in a new windowRed Roof Inn PLUS+ West Springfield
Wagon Wheel Inn

Wagon Wheel Inn

2 out of 5
484 Pittsfield Rd, PO Box 808, Lenox, MA
$69 nightly
The price is $77 total per night from Sep 20 to Sep 21
$77 total
Sep 20 - Sep 21
Total with taxes and fees
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood ...
7/10 Good! (626 reviews)
"And I mean the David Lynch as a compliment."

Reviewed on Aug 14, 2025

Opens in a new windowWagon Wheel Inn
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Lantern House Motel

Lantern House Motel

2.5 out of 5
256 Stockbridge Road, Great Barrington, MA
Stay at this motel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Housatonic River and Lake Mansfield Park are located ...
Avoid staying here if you can.
"The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should ..."

Reviewed on Nov 22, 2021

Get rates
Opens in a new windowLantern House Motel
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 Western Massachusetts

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
26 Glendale Road, RR 183, Stockbridge, MA
$335 nightly
The price is $374 total per night from Oct 6 to Oct 7
$374 total
Oct 6 - Oct 7
Total with taxes and fees
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...
"Very expensive for a small room. My son and I could barely sleep in this remote quiet place. Staffs were very friendly."

Reviewed on Nov 2, 2024

Opens in a new windowThe Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Hotel Northampton

Hotel Northampton

3.5 out of 5
36 King Street, Northampton, MA
$165 nightly
The price is $184 total per night from Sep 21 to Sep 22
$184 total
Sep 21 - Sep 22
Total with taxes and fees
Stay at this 3.5-star historic hotel in Northampton. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,004 reviews)
"Wonderful stay at the hotel. Can recommend 100%"

Reviewed on Sep 13, 2025

Opens in a new windowHotel Northampton
The Orchards Hotel

The Orchards Hotel

2.5 out of 5
222 Adams Rd, Williamstown, MA
Book a stay at this business-friendly hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Colonial Plaza and Linear ...
"A little dated. Restaurant shut down for renovations, disappointing"

Reviewed on Mar 9, 2020

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Opens in a new windowThe Orchards Hotel
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Lantern House Motel

Lantern House Motel

2.5 out of 5
256 Stockbridge Road, Great Barrington, MA
Stay at this motel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Housatonic River and Lake Mansfield Park are located ...
Avoid staying here if you can.
"The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should ..."

Reviewed on Nov 22, 2021

Get rates
Opens in a new windowLantern House Motel
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 Western Massachusetts

Vacation Village in the Berkshires
Great for families

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
$97 nightly
The price is $108 total per night from Oct 2 to Oct 3
$108 total
Oct 2 - Oct 3
Total with taxes and fees
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,004 reviews)

Families like: Kids pool, playground, game room, skiing nearby

Travelers say...
"Quiet, clean, beautifully landscaped- such a comfy bed!"

Reviewed on Sep 13, 2025

Opens in a new windowVacation Village in the Berkshires
La Quinta Inn & Suites by Wyndham Springfield MA
Great for families

La Quinta Inn & Suites by Wyndham Springfield MA

3 out of 5
100 Congress Street, Springfield, MA
$118 nightly
The price is $134 total per night from Oct 19 to Oct 20
$134 total
Oct 19 - Oct 20
Total with taxes and fees
Book a stay at this family-friendly hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
8/10 Very Good! (1,261 reviews)

Families like: Indoor pool, game room, cribs, free breakfast for the whole family

Travelers say...
"Average hotel /clean room /bathroom didn’t open all the way due to shower curtain /caulk job around tub is horrible/ pool walls where peeling / pool was peeling as well /hotel needs some work"

Reviewed on Sep 5, 2025

Opens in a new windowLa Quinta Inn & Suites by Wyndham Springfield MA
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd, Holyoke, MA
$158 nightly
The price is $177 total per night from Sep 28 to Sep 29
$177 total
Sep 28 - Sep 29
Total with taxes and fees
Stay at this 3-star spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (2,231 reviews)
"Beautiful facility. Unfortunately we arrived after 8 pm and restaurant and bar were closed and are also closed on Monday. I did find it odd that all dining options on site are not available on Mondays. It should be noted that Northampton has lots of dining options, although some are also closed on ..."

Reviewed on Sep 15, 2025

Opens in a new windowD. Hotel Suites & Spa
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Blue - A Modern Hotel, Ascend Hotel Collection

Blue - A Modern Hotel, Ascend Hotel Collection

2.5 out of 5
1080 Riverdale St, West Springfield, MA
$118 nightly
The price is $135 total per night from Oct 19 to Oct 20
$135 total
Oct 19 - Oct 20
Total with taxes and fees
Book a stay at this business-friendly hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Big E and Eastern ...
10/10 Exceptional! (3 reviews)
"It's a beautiful hotel. The staff were some of the friendliest people I've met. I'll be back next month."

Reviewed on Sep 15, 2025

Opens in a new windowBlue - A Modern Hotel, Ascend Hotel Collection
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 Western Massachusetts Flight and Hotel Packages

Western Massachusetts flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Price was $674, price is now $577 per person
$577
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Albany (ALB)
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was $744, price is now $648 per person
$648
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Albany (ALB)
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Need a Car For After Your Flight?

Standard

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

$60

$160 total
found 2 days ago
Standard undefined

Special

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

$60

$161 total
found 2 days ago
Special undefined

Economy Special

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

$64

$128 total
found 2 days ago
Economy Special undefined

Fullsize

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

$64

$169 total
found 2 days ago
Fullsize undefined
Lowest prices found within the past 2 days. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Western Massachusetts?
Based on prices found over the last seven days, a roundtrip flight to Western Massachusetts was as low as $84. If you're flexible with your dates, it will be easy to land a great bargain. This price was available on Travelocity for flights to Western Massachusetts departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Western Massachusetts?
If you're thinking of booking a trip to Western Massachusetts, October is the cheapest time to fly there. This is based on Travelocity's direct return flight demand between January and December last year. Choose your dates and secure your spot today.
How can I check my flight status to Western Massachusetts?
Whether you'd like to view the status of your flight to Western Massachusetts or make changes to your itinerary, you'll find all the necessary details on our customer portal, Trips. Click on "Trips" at the top of our homepage, then log in or open a new account. Another convenient way to view and manage all your bookings is with the Travelocity app. Get real-time notifications about your flight and quickly share updates with any family flying with you.
How do I find the best deals on flights to Western Massachusetts?
Here are our tips — book early, avoid peak season and be flexible with your dates. If you don't have a specific date in mind, search for your flight to Western Massachusetts on Travelocity and click on "Flexible dates" above your results. This will help you locate any cheaper tickets on surrounding days. $84 was the most affordable price for a roundtrip flight to Western Massachusetts in the last seven days. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Western Massachusetts with Travelocity?
Search for cheap flights to Western Massachusetts with Travelocity and start packing for your next getaway. With 24/7 customer support during every step of your trip and our Price Match Guarantee, we take the difficulty out of finding cheap family flights, hotels, rental cars and more. Score a great deal today and brace yourself for an epic adventure.
What are the most popular flight routes to Western Massachusetts?
Browse through these major flight routes to Western Massachusetts and start planning your next vacation:

  • Chicago, IL (ORD-O'Hare Intl.) to Logan Intl. Airport (BOS) - 3,514 flights a month.
  • Washington, DC (DCA-Ronald Reagan Washington National) to Logan Intl. Airport (BOS) - 3,419 flights a month.
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Logan Intl. Airport (BOS) - 3,193 flights a month.

How much is a flight to Western Massachusetts on average?
Airfares for roundtrip flights to Western Massachusetts were priced between $84 and $888 in the last seven days. As soon as you find a terrific deal, lock it in and get ready to jet off on your next fun adventure with Travelocity. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Western Massachusetts?
The length of a direct flight to Western Massachusetts of course varies, but here are the average travel times for some common routes:

  • Chicago, IL (ORD-O'Hare Intl.) to Logan Intl. Airport (BOS) - 2 hours and 23 minutes
  • Washington, DC (DCA-Ronald Reagan Washington National) to Logan Intl. Airport (BOS) - 1 hour and 51 minutes
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Logan Intl. Airport (BOS) - 2 hours and 56 minutes

What can I expect on a flight to Western Massachusetts?
Factors like which carrier you choose and where your plane takes off from will largely determine your experience. You're likely to find all types of flights to Western Massachusetts, from cheap flights for family vacations to first class airfares. Warm meals, entertainment and games for the youngsters are just a little taste of what most airlines offer on long-haul services.

Plane Tickets To Western Massachusetts

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 Western Massachusetts. Browse through our inventory to explore a wide range of cheap flights to Western Massachusetts 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 Western Massachusetts as you anxiously await to exit the plane and explore what Western Massachusetts has to offer. Considering all the amazing local food and culture in Western Massachusetts, 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 Western Massachusetts 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 Western Massachusetts 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 Western Massachusetts 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 Western Massachusetts 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.