Cheap Flights to Middlesex County from $68 (2026/2027)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Middlesex County's top cities

A stone bridge over a calm river surrounded by lush greenery.

Marlborough

Flights
Marlborough

How Much Does it Cost To Fly To Middlesex County?

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

Mon, Feb 1 - Mon, Feb 8
MCO
Orlando Intl.
BOS
Logan Intl.
$118 Roundtrip, just found
$118
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Feb 1 from Orlando Intl. to Logan Intl., returning Mon, Feb 8, priced at $118 just found
Thu, Dec 3 - Sun, Dec 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$125 Roundtrip, found 6 days ago
$125
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Sun, Dec 6, priced at $125 found 6 days ago
Mon, Apr 19 - Wed, Apr 28
PIE
St. Petersburg-Clearwater Intl.
PSM
Portsmouth Intl.
$131 Roundtrip, found 9 hours ago
$131
Roundtrip
found 9 hours ago
Select Allegiant Air flight, departing Mon, Apr 19 from St. Petersburg-Clearwater Intl. to Portsmouth Intl., returning Wed, Apr 28, priced at $131 found 9 hours ago
Thu, Dec 10 - Mon, Dec 14
ORF
Norfolk Intl.
PVD
T.F. Green
$142 Roundtrip, found 3 hours ago
$142
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Thu, Dec 10 from Norfolk Intl. to T.F. Green, returning Mon, Dec 14, priced at $142 found 3 hours ago
Sat, Dec 5 - Sat, Dec 12
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$149 Roundtrip, found 4 days ago
$149
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Dec 5 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Dec 12, priced at $149 found 4 days ago
Thu, Jan 21 - Sat, Jan 30
MCO
Orlando Intl.
PVD
T.F. Green
$184 Roundtrip, found 1 day ago
$184
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jan 21 from Orlando Intl. to T.F. Green, returning Sat, Jan 30, priced at $184 found 1 day ago
Fri, Dec 11 - Sat, Dec 12
MCO
Orlando Intl.
BOS
Logan Intl.
$189 Roundtrip, just found
$189
Roundtrip
just found
Select Delta flight, departing Fri, Dec 11 from Orlando Intl. to Logan Intl., returning Sat, Dec 12, priced at $189 just found
Fri, Dec 11 - Mon, Dec 14
MCO
Orlando Intl.
BOS
Logan Intl.
$189 Roundtrip, just found
$189
Roundtrip
just found
Select JetBlue Airways flight, departing Fri, Dec 11 from Orlando Intl. to Logan Intl., returning Mon, Dec 14, priced at $189 just found
Thu, Jan 7 - Tue, Jan 12
MCO
Orlando Intl.
BOS
Logan Intl.
$226 Roundtrip, found 1 day ago
$226
Roundtrip
found 1 day ago
Select United flight, departing Thu, Jan 7 from Orlando Intl. to Logan Intl., returning Tue, Jan 12, priced at $226 found 1 day ago

Best Middlesex 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

Dec 10 - Dec 12

2 night stay

Dallas (DFW) to Boston (BOS)

American Airlines • Coach

Boston (BOS) to Dallas (DFW)

Frontier Airlines • Coach
Price was $889, price is now $542 per person
$542
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Nov 25 - Nov 29

4 night stay

Atlanta (ATL) to Boston (BOS)

Frontier Airlines • Roundtrip • Coach
Price was $1,914, price is now $1,189 per person
$1,189
per person
found 1 day ago
Raffles Boston
5.0-star property

Raffles Boston

Dec 23 - Dec 30

7 night stay

Atlanta (ATL) to Boston (BOS)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $3,073, price is now $2,120 per person
$2,120
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Dallas to Middlesex County
View all trips

Travelers ❤️ These Middlesex County 🏨

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway Everett MA
Book a stay at this luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
Opens in a new windowEncore Boston Harbor
Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

3.5 out of 5
320 Washington Street Newton MA
Book a stay at this business-friendly hotel in Newton. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
8.4/10 Very Good! (2,667 reviews)
"All excellent"

Reviewed on Nov 9, 2026

Opens in a new windowFour Points by Sheraton Boston Newton
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.
9/10 Wonderful! (2,757 reviews)
"Came in early and I was able to still check in with the help of the staff"

Reviewed on Nov 11, 2026

Opens in a new windowHyatt Regency Boston/Cambridge
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
enVision Hotel Boston Everett

enVision Hotel Boston Everett

2 out of 5
1834 Revere Beach Pkwy Everett MA
Book a stay at this business-friendly hotel in Everett. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
Opens in a new windowenVision Hotel Boston Everett
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 Middlesex County?
In the last seven days, the cheapest roundtrip flight to Middlesex County cost $118 on our site. Check out our incredible deals, book your tickets and start planning for your next exciting getaway. This price was available on Travelocity for flights to Middlesex County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Middlesex County?
With 17 airlines flying in and out of Middlesex County, finding your ideal flight should be a snap. If your destination is Marlborough, go for the popular carrier, Delta Air Lines. It operates about 3,059 services to this wonderful city a month.
What is the cheapest month to fly to Middlesex County?
If you're thinking of booking a vacation in Middlesex County, February is the cheapest period to take to the skies. This is according to Travelocity's direct return flight demand between January and December last year. Pick your travel dates and secure your seat today.
How can I check my flight status to Middlesex County?
Whether you'd like to check the status of your flight to Middlesex County or make some changes, you'll find all the details you need on our handy portal, Trips. Click on "Trips" at the top of our homepage, then sign in or open a new account. Another great way to manage and view your booking is with the Travelocity app. Get alerts about gate changes or flight delays and easily share updates with any friends or family flying with you.
How do I find the best deals on flights to Middlesex County?
It's better to book ahead, and if possible, avoid traveling during vacation periods. Another smart way to save is by clicking the "Flexible dates" box at the top of the page after searching for your flights. This will reveal ticket prices for surrounding days. In the last seven days, the lowest price for a return flight to Middlesex County was $118. 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 Middlesex County with Travelocity?
If you're looking for cheap flights to Middlesex County, you'll come across some enticing deals with Travelocity. From cheap family flights on low-cost airlines to flexible airfares, we've got it all. Experience a stress-free trip with our 24/7 Virtual Agent online chat, Price Match Guarantee and free cancellations with most hotels and activities. Start planning your schedule and prepare to jet off to this exciting destination.
How much is a flight to Middlesex County on average?
Roundtrip flights to Middlesex County were priced between $118 and $226 in the last seven days. If you see a plane fare you like, act quickly. Cheap deals don't last long! These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What can I expect on a flight to Middlesex County?
This will mostly depend on where you're taking off from and which airline you choose. There's likely to be a variety of flights to Middlesex County, from premium fares to cheap flights for family vacations. On long-haul flights, your carrier will usually provide entertainment and warm meals as well as games to keep your little ones amused.