Cheap Flights to Worcester County from $53 (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, Aug 29 - Sat, Sep 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 3 days ago
$122
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Aug 29 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 5, priced at $122 found 3 days ago
Thu, Aug 27 - Sat, Sep 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 1 day ago
$122
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Aug 27 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 5, priced at $122 found 1 day ago
Thu, Sep 10 - Thu, Sep 17
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$126 Roundtrip, found 2 days ago
$126
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Portsmouth Intl., returning Thu, Sep 17, priced at $126 found 2 days ago
Thu, Aug 13 - Sat, Aug 29
MCO
Orlando Intl.
BOS
Logan Intl.
$126 Roundtrip, found 8 hours ago
$126
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Thu, Aug 13 from Orlando Intl. to Logan Intl., returning Sat, Aug 29, priced at $126 found 8 hours ago
Thu, Aug 27 - Sun, Sep 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$127 Roundtrip, found 20 hours ago
$127
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Thu, Aug 27 from Orlando Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $127 found 20 hours ago
Sat, Aug 29 - Wed, Sep 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$133 Roundtrip, found 5 days ago
$133
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Aug 29 from Orlando Intl. to Bradley Intl., returning Wed, Sep 2, priced at $133 found 5 days ago
Sat, Aug 22 - Sat, Aug 29
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$165 Roundtrip, found 9 hours ago
$165
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Sat, Aug 22 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Aug 29, priced at $165 found 9 hours ago
Thu, Aug 27 - Wed, Sep 2
MCO
Orlando Intl.
PVD
T.F. Green
$165 Roundtrip, found 12 hours ago
$165
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Thu, Aug 27 from Orlando Intl. to T.F. Green, returning Wed, Sep 2, priced at $165 found 12 hours ago
OriginDestinationTravel DatesFlights From*
MCOPortsmouthAugust 29 to September 5$122
MCOPortsmouthAugust 29 to September 5$122
MCOWindsor LocksAugust 27 to August 31$134
FLLWindsor LocksSeptember 10 to September 16$163
FLLWarwickSeptember 10 to September 16$165
MCOWarwickSeptember 10 to September 17$189
MCOWarwickSeptember 10 to September 17$189
FLLBostonSeptember 8 to September 10$208
FLLLondonderrySeptember 25 to September 26$217
FLLWorcesterJuly 30 to August 4$228
MCOWorcesterSeptember 19 to September 26$272
MCOWorcesterSeptember 19 to September 26$272
PHLWorcesterAugust 6 to August 13$357
PHLLondonderrySeptember 8 to September 11$451
RSWWorcesterAugust 3 to August 12$757
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCOPortsmouthJuly 11 to July 18$183
MCOPortsmouthJuly 11 to July 18$183
MCOWindsor LocksJuly 11 to July 18$253
MCOWindsor LocksJuly 11 to July 18$253
MCOWarwickJuly 11 to July 17$291
MCOWarwickJuly 11 to July 17$291
FLLWindsor LocksJuly 11 to July 13$325
RSWWarwickJuly 10 to July 11$326
FLLWarwickJuly 11 to July 20$342
MCOWorcesterJuly 10 to July 15$382
MCOWorcesterJuly 10 to July 15$382
MCOLondonderryJuly 11 to July 25$416
MCOLondonderryJuly 11 to July 25$416
FLLBostonJuly 10 to July 14$435
FLLWorcesterJuly 10 to July 16$447
*Prices include taxes and fees

Best Worcester County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Sep 4 - Sep 7

3 night stay

Dallas (DAL) to Boston (BOS)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,079, price is now $1,209 per person
$1,209
per person
found 1 day ago
The Atlas Hotel
4.5-star property

The Atlas Hotel

Sep 23 - Sep 30

7 night stay

Dallas (DAL) to Boston (BOS)

Delta • Coach

Boston (BOS) to Dallas (DAL)

Frontier Airlines • Coach
Save 100% on your flight
Price was $2,339, price is now $1,344 per person
$1,344
per person
found 1 day ago
Nantucket Inn
3.5-star property

Nantucket Inn

Aug 12 - Aug 16

4 night stay

Dallas (DFW) to Boston (BOS)

Southwest Airlines • Non-stop • Coach

Boston (BOS) to Dallas (DFW)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,563, price is now $1,566 per person
$1,566
per person
found 1 day ago
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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.
8.6/10 Excellent! (1,009 reviews)
"So beautiful I like it thank you 🌼"

Reviewed on Jul 6, 2026

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.
9/10 Wonderful! (1,703 reviews)
"Lovely, historic inn with excellent food & service."

Reviewed on Jul 6, 2026

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! (1,579 reviews)
"I stayed for a wedding, which there were 4 other events happening, and they closed the bar before our wedding came back. We book it for an after party and then there was no bar. I don’t understand how this was lost in communication regarding staffing. Aside from that my stay was lovely."

Reviewed on Jul 7, 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 Vietnam Mountain Biking Trail and The Tasting Room - An Italian Wine Shop are located nearby.
8/10 Very Good! (1,004 reviews)
"Enjoyed our stay"

Reviewed on Jul 3, 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 $122 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, August 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 $122. 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 $122 and $757 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.