Cheap Flights to Worcester County from $61 (2026/2027)

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Worcester

Flights
Worcester

How Much Does it Cost To Fly To Worcester County?

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

Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$108 Roundtrip, found 5 days ago
$108
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Nov 7 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $108 found 5 days ago
Sat, Oct 31 - Sat, Nov 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 6 days ago
$117
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 14, priced at $117 found 6 days ago
Sat, Oct 24 - Sat, Oct 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$118 Roundtrip, found 5 days ago
$118
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Oct 24 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 31, priced at $118 found 5 days ago
Sat, Oct 24 - Sat, Oct 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$128 Roundtrip, found 4 days ago
$128
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Oct 24 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 31, priced at $128 found 4 days ago
Thu, Dec 3 - Mon, Dec 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$130 Roundtrip, found 4 days ago
$130
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Bradley Intl., returning Mon, Dec 7, priced at $130 found 4 days ago
Wed, Dec 9 - Wed, Dec 16
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$135 Roundtrip, found 5 hours ago
$135
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Wed, Dec 9 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Dec 16, priced at $135 found 5 hours ago
Wed, Oct 28 - Tue, Nov 10
MCO
Orlando Intl.
BOS
Logan Intl.
$171 Roundtrip, found 2 hours ago
$171
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Oct 28 from Orlando Intl. to Logan Intl., returning Tue, Nov 10, priced at $171 found 2 hours ago
Thu, Dec 10 - Thu, Dec 17
MCO
Orlando Intl.
BDL
Bradley Intl.
$174 Roundtrip, found 4 days ago
$174
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Dec 10 from Orlando Intl. to Bradley Intl., returning Thu, Dec 17, priced at $174 found 4 days ago
OriginDestinationTravel DatesFlights From*
SFBPortsmouthJanuary 10 to January 17$102
FLLBostonJanuary 9 to January 10$129
MCOLondonderryDecember 9 to December 16$135
FLLWindsor LocksOctober 29 to November 2$164
MCOWindsor LocksJanuary 13 to January 20$168
MCOWindsor LocksJanuary 13 to January 20$168
FLLWarwickJanuary 15 to January 25$173
MCOWarwickDecember 3 to December 12$204
FLLLondonderryNovember 10 to November 11$257
MCOWorcesterNovember 4 to November 7$362
MCOWorcesterNovember 4 to November 7$362
PHLLondonderryOctober 22 to October 29$388
RSWWorcesterNovember 19 to November 22$400
FLLWorcesterOctober 29 to November 5$435
SJUWorcesterNovember 2 to November 9$439
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCOPortsmouthOctober 10 to October 17$230
MCOPortsmouthOctober 10 to October 17$230
RSWWarwickOctober 10 to October 24$266
MCOWindsor LocksOctober 10 to October 14$313
MCOWindsor LocksOctober 10 to October 14$313
TTNBostonOctober 11 to October 14$317
MCOWarwickOctober 11 to October 18$323
MCOWarwickOctober 11 to October 18$323
FLLWindsor LocksOctober 9 to October 12$378
RSWBostonOctober 10 to November 3$413
PHLWindsor LocksOctober 11 to October 31$517
MCOWorcesterOctober 10 to October 16$519
MCOWorcesterOctober 10 to October 16$519
FLLWorcesterOctober 11 to November 7$549
FLLBostonOctober 10 to October 13$559
*Prices include taxes and fees

Best Worcester County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
4.0-star property

Boston Lodge and Suites

Nov 9 - Nov 12

3 night stay

Dallas (DFW) to Boston (BOS)

Southwest Airlines • Roundtrip • Coach
Price was $1,346, price is now $645 per person
$645
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Dec 10 - Dec 13

3 night stay

Dallas (DAL) to Boston (BOS)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,725, price is now $1,041 per person
$1,041
per person
found 1 day ago
Four Seasons Hotel Boston
5.0-star property

Four Seasons Hotel Boston

Nov 5 - Nov 8

3 night stay

Denver (DEN) to Boston (BOS)

Delta • Coach

Boston (BOS) to Denver (DEN)

Southwest Airlines • Coach
Save 100% on your flight
Price was $1,996, price is now $1,285 per person
$1,285
per person
found 1 day ago
Don't see what you're looking for?
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Travelers ❤️ These Worcester County 🏨

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
Book a stay at this family-friendly resort in Fitchburg. Enjoy 4 indoor pools, free water park access, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Great Wolf Lodge Waterpark and Wachusett Brewing Company are located nearby.
Opens in a new windowGreat Wolf Lodge Boston / Fitchburg, MA
Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

2.5 out of 5
277 Main Street (RT 131) Sturbridge MA
Book a stay at this spa resort in Sturbridge. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Town Common and Sturbridge Common Historic District are located nearby.
Opens in a new windowPublick House Historic Inn and Country Motor Lodge
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St Southbridge MA
Book a stay at this business-friendly hotel in Southbridge. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Central Mills Historic District and Southbridge Town Common are located nearby.
9.2/10 Wonderful! (1,677 reviews)
"This is our 6th time staying here, we love it. Its our Home away from Home❤️ The amenities are so nice its such a relaxing atmosphere and always a clean hotel stay every time. We are so grateful for this place!"

Reviewed on Oct 1, 2026

Opens in a new windowWellsworth Hotel
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Sonesta Select Boston Milford

Sonesta Select Boston Milford

3 out of 5
10 Fortune Blvd Milford MA
Book a stay at this business-friendly hotel in Milford. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions The Tasting Room - An Italian Wine Shop and Hopkinton Center for the Arts are located nearby.
7.6/10 Good! (1,000 reviews)
"Room was very cleaning staff was great 👍"

Reviewed on Sep 27, 2026

Opens in a new windowSonesta Select Boston Milford
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.

Frequently asked questions

How much is the cheapest flight to Worcester County?
To give you a figure to work with, the cheapest roundtrip flight to Worcester County was $102 within the last seven days. An excellent way to nab a travel bargain is to be flexible with your dates. This price was available on Travelocity for flights to Worcester County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Worcester County?
Pack your bags and jet away with one of the 15 airlines that fly to Worcester County. Secure a seat with the renowned carrier, Delta Air Lines. It has approximately 3,059 flights a month to Milford, Worcester County's primary city, so finding the right fare should be a snap.
What is the cheapest month to fly to Worcester County?
If you have your heart set on a trip to Worcester County, November is the cheapest month to make your way there. This is according to Travelocity's direct return flight demand between January and December last year. Pick your travel dates and book your spot today.
How can I check my flight status to Worcester County?
Get useful updates about any changes to your flights and gate numbers with Trips. This handy customer portal can be found at the top of our homepage and is where you can view and manage your bookings. Create your account in a matter of moments and you're ready. The Travelocity app makes it possible for you to check the details of your flight to Worcester County while you're on the go — and even while you're offline. The app has all your booking needs covered. Whether you want to organize transportation to or from the airport or share your travel itinerary with any members of your family flying with you, the app is your one-stop travel shop.
How do I find the best deals on flights to Worcester County?
Be flexible with your dates and there's a good chance you'll find a sensational deal. After you've searched for flights on Travelocity, click "Flexible dates" above your results to compare prices with surrounding days. Also try to book ahead of schedule and avoid vacation periods. In the last seven days, the best price for a roundtrip flight to Worcester County was $102. 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 Worcester County with Travelocity?
From cheap flights to Worcester County to all-inclusive resorts and activities, Travelocity has got you covered for incredible adventures. With everything you need in one place, you can enjoy more time preparing for the cool things that are waiting for you in Worcester County and less time on the travel details. Plus with our Price Match Guarantee and free cancellation on most hotels, our mission is to make your next vacation a stress-free one.
What are the most popular flight routes to Worcester County?
To help you choose your flights to Worcester County, here's a list of some of the well-known routes:

  • 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 Worcester County on average?
Airfares for roundtrip flights to Worcester County cost between $102 and $559 in the last seven days. The moment you see a good deal, snap it up and get ready to jet off on the vacation of your dreams 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 Worcester County?
Check out these major routes for an idea of how long you'll be in your seat during a direct flight to Worcester County:

  • 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 Worcester County?
If you're about to jump on a long-haul flight to Worcester County, you can normally expect drinks, meals and entertainment on board. Airlines strive to make longer flights as comfortable as they can. Shorter journeys — along with flights offered by low-cost airlines — may not come with such inclusions. If you're looking for cheap flights for family vacations with a low-priced carrier, be prepared to pay extra for entertainment and food.