Flights To Middlesex County - Cheap Flights Starting at CA $87

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

An aerial view of a town with a central square, a church, and surrounding residential areas.

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.

Thu, Dec 3 - Sun, Dec 6
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
CA $187 Roundtrip, found 1 day ago
CA $187
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Dec 3 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Dec 6, priced at CA $187 found 1 day ago
Thu, Feb 18 - Sun, Feb 21
RDU
Raleigh - Durham Intl.
PVD
T.F. Green
CA $238 Roundtrip, found 6 days ago
CA $238
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Feb 18 from Raleigh - Durham Intl. to T.F. Green, returning Sun, Feb 21, priced at CA $238 found 6 days ago
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
BOS
Logan Intl.
CA $241 Roundtrip, found 5 hours ago
CA $241
Roundtrip
found 5 hours ago
Select Delta flight, departing Sat, Nov 7 from Orlando Intl. to Logan Intl., returning Sat, Nov 14, priced at CA $241 found 5 hours ago
Sat, Oct 24 - Sat, Oct 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
CA $245 Roundtrip, found 1 day ago
CA $245
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Oct 24 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 31, priced at CA $245 found 1 day ago
Wed, Oct 21 - Sat, Oct 31
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
CA $281 Roundtrip, found 1 day ago
CA $281
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Oct 21 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Oct 31, priced at CA $281 found 1 day ago
Tue, Oct 27 - Tue, Nov 3
MCO
Orlando Intl.
PVD
T.F. Green
CA $304 Roundtrip, found 3 days ago
CA $304
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Oct 27 from Orlando Intl. to T.F. Green, returning Tue, Nov 3, priced at CA $304 found 3 days ago
Sat, Nov 7 - Sat, Nov 14
MCO
Orlando Intl.
BOS
Logan Intl.
CA $312 Roundtrip, found 5 hours ago
CA $312
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Sat, Nov 7 from Orlando Intl. to Logan Intl., returning Sat, Nov 14, priced at CA $312 found 5 hours ago
Thu, Nov 26 - Tue, Dec 1
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $355 Roundtrip, found 1 hour ago
CA $355
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Nov 26 from Pearson Intl. to Logan Intl., returning Tue, Dec 1, priced at CA $355 found 1 hour ago
Tue, Nov 17 - Mon, Nov 23
MCO
Orlando Intl.
BOS
Logan Intl.
CA $369 Roundtrip, found 4 days ago
CA $369
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Nov 17 from Orlando Intl. to Logan Intl., returning Mon, Nov 23, priced at CA $369 found 4 days ago
Thu, Oct 29 - Mon, Nov 2
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $462 Roundtrip, just found
CA $462
Roundtrip
just found
Select Air Transat flight, departing Thu, Oct 29 from Pearson Intl. to Logan Intl., returning Mon, Nov 2, priced at CA $462 just found
Tue, Oct 20 - Tue, Oct 27
YYZ
Pearson Intl.
PVD
T.F. Green
CA $527 Roundtrip, found 1 day ago
CA $527
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 20 from Pearson Intl. to T.F. Green, returning Tue, Oct 27, priced at CA $527 found 1 day ago
Price found within the past 48 hours. Click for updated prices.
Raffles Boston
5.0-star property

Raffles Boston

Nov 20 - Nov 23

3 night stay

Toronto (YYZ) to Boston (BOS)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $2,365, price is now CA $1,683 per person
CA $1,683
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Nov 20 - Nov 24

4 night stay

Calgary (YYC) to Boston (BOS)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $2,831, price is now CA $1,754 per person
CA $1,754
per person
found 1 day ago
Hotel AKA Boston Common
4.0-star property

Hotel AKA Boston Common

Nov 2 - Nov 9

7 night stay

Calgary (YYC) to Boston (BOS)

Porter Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $3,333, price is now CA $2,416 per person
CA $2,416
per person
found 21 hours ago
Don't see what you're looking for?
See all available trips from Toronto 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.
9.6/10 Exceptional! (4,243 reviews)
"Great"

Reviewed on Oct 7, 2026

Opens in a new windowEncore Boston Harbor
Lakeside Inn

Lakeside Inn

2 out of 5
595 North Ave Wakefield MA
Book a stay at this business-friendly hotel in Wakefield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attraction MarketStreet Lynnfield is located nearby.
8.2/10 Very good! (974 reviews)
"No refrigerator. Had a leaky bathroom sink and the water was so hot it almost scalded you. The carpets needed to be removed as they had cigarette burns and were filthy. Someone was running down the hallways in the early morning hours so could not sleep. Would never stay here agin."

Reviewed on Oct 8, 2026

Opens in a new windowLakeside Inn
La Quinta Inn & Suites by Wyndham Boston Somerville

La Quinta Inn & Suites by Wyndham Boston Somerville

3 out of 5
23 Cummings St Somerville MA
Book a stay at this business-friendly hotel in Somerville. Enjoy free breakfast, free WiFi, and a free airport shuttle. 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 windowLa Quinta Inn & Suites by Wyndham Boston Somerville
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
The Royal Sonesta Boston

The Royal Sonesta Boston

4 out of 5
40 Edwin H. Land Boulevard Cambridge MA
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
Opens in a new windowThe Royal Sonesta Boston
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 CA $187 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 20 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, December 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 CA $187. 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 CA $187 and CA $527 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.