$57 Cheap flights to Middlesex County

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Top places to visit in Middlesex County

A river with a wooden bridge, surrounded by dense green foliage.
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Lowell

Lowell
A town with a prominent white church steeple, a snow-covered landscape, and a mix of residential and commercial buildings.
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Chelmsford

Chelmsford
An aerial view of a beach surrounded by autumn-colored trees.
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Westford

Westford

Cheap flights to Middlesex County from $57 One Way, $112 Round Trip

$112 return flights and $57 one-way flights to Middlesex County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Oct 31 - Sat, Nov 7
MCO
Orlando
PSM
Portsmouth
$112 Roundtrip, found 6 days ago
$112
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando to Portsmouth, returning Sat, Nov 7, priced at $112 found 6 days ago
Wed, Nov 4 - Wed, Nov 11
MCO
Orlando
MHT
Manchester
$123 Roundtrip, found 2 days ago
$123
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Nov 4 from Orlando to Manchester, returning Wed, Nov 11, priced at $123 found 2 days ago
Sat, Oct 24 - Sat, Oct 31
MCO
Orlando
BOS
Boston
$126 Roundtrip, found 4 days ago
$126
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Oct 24 from Orlando to Boston, returning Sat, Oct 31, priced at $126 found 4 days ago
Sat, Jan 23 - Mon, Feb 1
TPA
Tampa
PVD
Providence
$141 Roundtrip, found 20 hours ago
$141
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Sat, Jan 23 from Tampa to Providence, returning Mon, Feb 1, priced at $141 found 20 hours ago
Mon, Apr 19 - Wed, Apr 28
PIE
St. Petersburg
PSM
Portsmouth
$150 Roundtrip, found 3 days ago
$150
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Mon, Apr 19 from St. Petersburg to Portsmouth, returning Wed, Apr 28, priced at $150 found 3 days ago
Sat, Oct 10 - Tue, Oct 13
TPA
Tampa
BOS
Boston
$179 Roundtrip, just found
$179
Roundtrip
just found
Select JetBlue Airways flight, departing Sat, Oct 10 from Tampa to Boston, returning Tue, Oct 13, priced at $179 just found
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Find The Perfect Hotel For After Your Flight

Score Epic Middlesex County Accommodation Deals

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway Everett MA
Fully refundableReserve now, pay when you stay
$328 nightly
The price is $367 total per night from Oct 12 to Oct 13
$367 total
Oct 12 - Oct 13
Total with taxes and fees
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 ...
Opens in a new windowEncore Boston Harbor
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
$182 nightly
The price is $210 total per night from Sep 20 to Sep 21
$210 total
Sep 20 - Sep 21
Total with taxes and fees
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 ...
9/10 Wonderful! (2,646 reviews)
"It was beautiful"

Reviewed on Sep 15, 2026

Opens in a new windowHyatt Regency Boston/Cambridge
Lakeside Inn

Lakeside Inn

2 out of 5
595 North Ave Wakefield MA
Fully refundable
$107 nightly
The price is $119 total per night from Sep 27 to Sep 28
$119 total
Sep 27 - Sep 28
Total with taxes and fees
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 ...
Opens in a new windowLakeside Inn
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Hilton Garden Inn Tewksbury Andover

Hilton Garden Inn Tewksbury Andover

3 out of 5
4 Highwood Drive Tewksbury MA
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $117 total per night from Oct 4 to Oct 5
$117 total
Oct 4 - Oct 5
Total with taxes and fees
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 ...
9/10 Wonderful! (1,443 reviews)
"Todo muy bien"

Reviewed on Sep 15, 2026

Opens in a new windowHilton Garden Inn Tewksbury Andover
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.

Need a Car For After Your Flight?

Economy

Mitsubishi Mirage
  • 4 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Mitsubishi Mirage

$48

$262 total
found 1 day ago
Economy Mitsubishi Mirage

Compact

Nissan Versa
  • 5 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Nissan Versa

$48

$265 total
found 1 day ago
Compact Nissan Versa

Mini Van

Chrysler Pacifica
  • 7 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Chrysler Pacifica

$49

$267 total
found 1 day ago
Mini Van Chrysler Pacifica

Midsize

Toyota Corolla
  • 5 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Toyota Corolla

$50

$272 total
found 1 day ago
Midsize Toyota Corolla

Middlesex County

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First-Timers

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Ports and Play

Be sure to check our cruise page for free shore excursions, onboard spending, balcony upgrades and other perks. Orbitz offers last-minute, luxury, weekend and summer cruises. You can even designate which port you want to sail from and pre-book on-shore activities. Get there on the cheap with discounts on flights to Middlesex County and Middlesex County flights. Get more bang for your travel buck at Orbitz.

Frequently asked questions

What is the best airport to fly to in Middlesex County?
Fly into Laurence G. Hanscom Field Airport (BED), the primary entry point to Middlesex County. Organizing your flight to this region doesn't get much easier than that.
How much is a flight to Middlesex County?
Last week, prices fluctuated between $112 and $179 for a return trip to Middlesex County. One-way flights departing from Orlando (MCO) dropped down to $57 during the same period.
How to book the cheapest flight to Middlesex County?
With some of the biggest and best flight deals around, you're guaranteed value for money with Orbitz. The following hints and tips will help you pick up cheap flights to Middlesex County — and leave you with cash to spare:

  • Depending on where you're departing from, click on the 'Nearby airports' function (located under the departure and arrival options). In some cases, alternative departure points offer cheaper airfares.
  • Also, click on the 'Show flexible dates' link to see the prices on days either side of your selected departure. It's possible to score cheaper flight deals if you're flexible with your plans.
  • Hit 'Show options' to filter your search results. You can choose your preferred airline and seating class here. Under 'Sort & Filter' to the left, you can even specify whether you'd like to fly in the morning, afternoon or evening.
  • Reserve your airfare as soon as you've decided on your travel dates. While it does happen now and then, airline tickets rarely fall in price as your departure date nears.
  • Save more on your vacation by combining your hotel, flights and car rental into a package with Orbitz. Your credit card will thank you.
  • Don't fly during peak seasons if you can. By avoiding summer, school vacations and other popular dates, you can save loads on your airfare.

What is the best time to book a flight to Middlesex County?
If possible, book your flights to Middlesex County in January. This is the best month to reserve low airfares, followed by February and August. With a bit of organizing, you're sure to find a cheap flight with Orbitz.
What day of the week is the cheapest to book a flight to Middlesex County?
When it comes to cheap flights to Middlesex County, the best days to make a booking are generally Tuesdays, Wednesdays and Saturdays. A rewarding flight deal is just clicks away with Orbitz.
What is the cheapest day of the week to fly to Middlesex County?
You can land cheap flights to Middlesex County by taking off on a Monday, according to Orbitz data from 2020. Tuesday is the next cheapest day, while Saturday has the most expensive ticket prices. Whether you prefer to save cash or fly out whenever is convenient, you'll always get a rewarding deal with Orbitz.
What is the cheapest month to fly to Middlesex County?
According to Orbitz data, you'll want to fly out in August. This is generally the best month to pick up cheap flights to Middlesex County. It's worth bearing in mind that the most expensive time to jet off is in June.
Which airlines allow free cancellation?
Plans change, and we think your ticket should be able to as well. That's why Orbitz makes it a cinch to search for fares with no change fees and free cancellation. Simply enter your departure and arrival destinations and then choose "Filter by flexible change policies." How's that for fuss-free?
What do I need for the flight to Middlesex County?
There is so much to sort out for any big journey, so it's good to get a bit of help before you set out. Here are a few tips to make sure you're ready for your flight:

  • Travel paperwork such as e-tickets and some identification will be required. To avoid any last-minute delays when you check in, ensure that your booking is under the same name, gender and birth date as listed on your government-issued ID.
  • A properly packed carry-on bag is just the ticket for flying in comfort. Given your flight to Middlesex County is no short hop, take enough snacks and things to keep you occupied. A book, magazine or e-reader will help the hours pass.
  • Never mind what the weather is outside, plane cabins can often get quite cold. Take an extra layer on your journey to stay cozy and warm.

How do I get cheap first-class/business deals to Middlesex County?
If you think a business or first-class airfare is out of your reach, think again. Here are just a few tips to help you book a premium flight to Middlesex County for a whole lot less:

  • Flexibility isn't just a yoga thing. Avoid locking in your travel dates so you can pick up cheaper airfares when they crop up.
  • Budget airlines offer first or business-class seats at more affordable prices. Give the full-service carriers a miss and look into these cheaper options.
  • Take advantage of your airline's loyalty program and upgrade your seat. You can also bid for an upgrade in online auctions.

What is the best time to go to Middlesex County?
If you'd like to experience the unique vibe of Middlesex County in the peak season, June, July and August are the best months to visit. June 20 heralds the onset of the summer season in the Northern Hemisphere and is an awesome time to travel if you savor being outside. Around this time of the year, average daily temperatures generally range from 60 ºF to 80 ºF.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.