$51 Cheap flights to Middlesex County

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Top places to visit in Middlesex County

A calm river with red brick buildings on one side and a tree in the center.
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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 $51 One Way, $117 Round Trip

$117 return flights and $51 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, Jan 16 - Sat, Jan 23
MCO
Orlando
PSM
Portsmouth
$117 Roundtrip, found 2 days ago
$117
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Jan 16 from Orlando to Portsmouth, returning Sat, Jan 23, priced at $117 found 2 days ago
Sat, Sep 19 - Sat, Oct 10
MCO
Orlando
BOS
Boston
$127 Roundtrip, found 5 days ago
$127
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Sep 19 from Orlando to Boston, returning Sat, Oct 10, priced at $127 found 5 days ago
Wed, Sep 16 - Sat, Sep 19
MCO
Orlando
MHT
Manchester
$129 Roundtrip, found 2 days ago
$129
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Sep 16 from Orlando to Manchester, returning Sat, Sep 19, priced at $129 found 2 days ago
Fri, Jan 22 - Mon, Jan 25
TPA
Tampa
PVD
Providence
$132 Roundtrip, found 3 days ago
$132
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Jan 22 from Tampa to Providence, returning Mon, Jan 25, priced at $132 found 3 days ago
Tue, Sep 8 - Fri, Sep 11
DEN
Denver
BOS
Boston
$156 Roundtrip, just found
$156
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Sep 8 from Denver to Boston, returning Fri, Sep 11, priced at $156 just found
Mon, Aug 31 - Fri, Sep 4
DEN
Denver
BOS
Boston
$159 Roundtrip, found 1 hour ago
$159
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Aug 31 from Denver to Boston, returning Fri, Sep 4, priced at $159 found 1 hour ago
Wed, Aug 26 - Fri, Aug 28
DEN
Denver
BOS
Boston
$165 Roundtrip, just found
$165
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Aug 26 from Denver to Boston, returning Fri, Aug 28, priced at $165 just found
Thu, Sep 17 - Tue, Sep 22
MCO
Orlando
PVD
Providence
$165 Roundtrip, found 3 days ago
$165
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Sep 17 from Orlando to Providence, returning Tue, Sep 22, priced at $165 found 3 days ago
Sat, Aug 15 - Sat, Aug 15
PIE
St. Petersburg
PSM
Portsmouth
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Sat, Aug 15 from St. Petersburg to Portsmouth, returning Sat, Aug 15, priced at $177 found 1 day ago
Tue, Oct 20 - Wed, Oct 28
DEN
Denver
BOS
Boston
$197 Roundtrip, found 22 hours ago
$197
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Tue, Oct 20 from Denver to Boston, returning Wed, Oct 28, priced at $197 found 22 hours ago
Thu, Oct 15 - Sat, Oct 17
DEN
Denver
BOS
Boston
$237 Roundtrip, found 1 hour ago
$237
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Oct 15 from Denver to Boston, returning Sat, Oct 17, priced at $237 found 1 hour ago
Tue, Jan 12 - Sat, Feb 20
DEN
Denver
BOS
Boston
$257 Roundtrip, just found
$257
Roundtrip
just found
Select Delta flight, departing Tue, Jan 12 from Denver to Boston, returning Sat, Feb 20, priced at $257 just found

Find The Perfect Hotel For After Your Flight

Score Epic Middlesex County Accommodation Deals

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $176 total per night from Sep 7 to Sep 8
$176 total
Sep 7 - Sep 8
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! (2,563 reviews)
"There was no air conditioning, which they didn't tell us about before checking in. Also, the shower was not functioning, so we were delayed in our activities until the situation was resolved. No one volunteered to compensate us in any way for all the inconvenience until we persisted. We were eventually ..."

Reviewed on Aug 7, 2026

Opens in a new windowHyatt Regency Boston/Cambridge
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway Everett MA
Fully refundableReserve now, pay when you stay
$244 nightly
The price is $273 total per night from Aug 30 to Aug 31
$273 total
Aug 30 - Aug 31
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 ...
9.6/10 Exceptional! (4,035 reviews)
"From the Front Desk to the Casino staff my husband and I felt like we were the most important folks staying at the hotel . The reality was we were weary travelers returning from a business meeting in Connecticut by train . Much more relaxing than driving until ... our train out of Connecticut was ..."

Reviewed on Aug 6, 2026

Opens in a new windowEncore Boston Harbor
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
$97 nightly
The price is $108 total per night from Aug 23 to Aug 24
$108 total
Aug 23 - Aug 24
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 ...
Opens in a new windowHilton Garden Inn Tewksbury Andover
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The Royal Sonesta Boston

The Royal Sonesta Boston

4 out of 5
40 Edwin H. Land Boulevard Cambridge MA
Fully refundableReserve now, pay when you stay
$201 nightly
The price is $233 total per night from Aug 16 to Aug 17
$233 total
Aug 16 - Aug 17
Total with taxes and fees
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 ...
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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Middlesex County

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Orbitz becomes your Mobile friend

You can now book flights to Middlesex County on the new cutting-edge mobile tool for Android or iPhone users. Hotel packages, flight updates and changes can all be accessed using this tool. When you make any reservations or bookings using this service, confirmation will be provided on the same day the request was made. Take advantage of Orbitz friendly service and low cost Middlesex County flights.

Discounted tickets available for flights to Middlesex County

Orbitz offers tickets at a discounted, budget friendly rate that will satisfy all of your travel requirements. Book your Middlesex County flights with us and structure a package that includes car hire, family activities and cheap accommodation. Orbitz will ensure that all your requirements are met, letting you relax and enjoy your holiday as it was intended.

Orbitz offers discounted Middlesex County flights

Discounted flights to Middlesex County ensure that all who want to travel can Take advantage of Orbitz’ guaranteed low prices and affordable packages. You will enjoy a hassle free trip, an up to date travel planner and friendly service.

Traveler profile updates

When flying with Orbitz, take advantage of frequent updates on your flights to Middlesex County. Details and updates are sent to up to six contact numbers to ensure that you are kept abreast of the latest information on Middlesex County flights. Frequent flyer and loyalty membership numbers may be updated within your Orbitz account profile.

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 $117 and $257 for a return trip to Middlesex County. One-way flights departing from Orlando (MCO) dropped down to $51 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.