Flights To Middlesex County - Cheap Flights Starting at CA $208

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.

Tue, Sep 15 - Thu, Sep 17
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $343 Roundtrip, just found
CA $343
Roundtrip
just found
Select Porter Airlines flight, departing Tue, Sep 15 from Pearson Intl. to Logan Intl., returning Thu, Sep 17, priced at CA $343 just found
Sun, Sep 20 - Sun, Sep 27
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $347 Roundtrip, just found
CA $347
Roundtrip
just found
Select Air Canada flight, departing Sun, Sep 20 from Pearson Intl. to Logan Intl., returning Sun, Sep 27, priced at CA $347 just found
Sun, Sep 20 - Sun, Sep 27
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $352 Roundtrip, just found
CA $352
Roundtrip
just found
Select Air Canada flight, departing Sun, Sep 20 from Pearson Intl. to Logan Intl., returning Sun, Sep 27, priced at CA $352 just found
Sat, Sep 19 - Sun, Sep 20
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $364 Roundtrip, just found
CA $364
Roundtrip
just found
Select Porter Airlines flight, departing Sat, Sep 19 from Pearson Intl. to Logan Intl., returning Sun, Sep 20, priced at CA $364 just found
Sun, Sep 20 - Sun, Sep 27
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $370 Roundtrip, just found
CA $370
Roundtrip
just found
Select Porter Airlines flight, departing Sun, Sep 20 from Pearson Intl. to Logan Intl., returning Sun, Sep 27, priced at CA $370 just found
Wed, Sep 16 - Mon, Sep 21
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $375 Roundtrip, just found
CA $375
Roundtrip
just found
Select Air Canada flight, departing Wed, Sep 16 from Pearson Intl. to Logan Intl., returning Mon, Sep 21, priced at CA $375 just found
Tue, Sep 22 - Tue, Sep 22
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $375 Roundtrip, found 1 hour ago
CA $375
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Sep 22 from Pearson Intl. to Logan Intl., returning Tue, Sep 22, priced at CA $375 found 1 hour ago
Wed, Sep 16 - Mon, Sep 21
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $378 Roundtrip, just found
CA $378
Roundtrip
just found
Select United flight, departing Wed, Sep 16 from Pearson Intl. to Logan Intl., returning Mon, Sep 21, priced at CA $378 just found
Thu, Sep 17 - Sun, Sep 20
YUL
Pierre Elliott Trudeau Intl.
BOS
Logan Intl.
CA $396 Roundtrip, found 2 hours ago
CA $396
Roundtrip
found 2 hours ago
Select Porter Airlines flight, departing Thu, Sep 17 from Pierre Elliott Trudeau Intl. to Logan Intl., returning Sun, Sep 20, priced at CA $396 found 2 hours ago
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
4.0-star property

Boston Lodge and Suites

Oct 21 - Oct 23

2 night stay

Toronto (YYZ) to Boston (BOS)

Porter Airlines • Roundtrip • Coach
Price was CA $1,366, price is now CA $810 per person
CA $810
per person
found 14 hours ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Oct 29 - Nov 2

4 night stay

Ottawa (YOW) to Boston (BOS)

Porter Airlines • Roundtrip • Coach
Price was CA $3,230, price is now CA $2,072 per person
CA $2,072
per person
found 1 day ago
Luxury Apartments by Hyatus at Boston Everett
5.0-star property

Luxury Apartments by Hyatus at Boston Everett

Oct 1 - Oct 4

3 night stay

Toronto (YYZ) to Boston (BOS)

Porter Airlines • Roundtrip • Coach
Price was CA $2,057, price is now CA $1,374 per person
CA $1,374
per person
found 11 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.
Opens in a new windowEncore Boston Harbor
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.
Opens in a new windowHyatt Regency Boston/Cambridge
Hilton Garden Inn Tewksbury Andover

Hilton Garden Inn Tewksbury Andover

3 out of 5
4 Highwood Drive Tewksbury MA
Book a stay at this business-friendly hotel in Tewksbury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Public Health Museum and Eastern Canal Park are located nearby.
8.8/10 Excellent! (1,331 reviews)
"No"

Reviewed on Aug 23, 2026

Opens in a new windowHilton Garden Inn Tewksbury Andover
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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.
Opens in a new windowLakeside Inn
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 $343 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, September 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 $343. 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 $343 and CA $396 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.