$53 Cheap flights to Middlesex County

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Top places to visit in Middlesex County

Lowell Canal in National Historic Park, Lowell, Massachusetts, USA
FlightsFlights
FlightsFlights

Lowell

Lowell
An aerial view of a beach surrounded by colorful autumn foliage.
FlightsFlights
FlightsFlights

Westford

Westford
Aerial view of Chelmsford, Massachusetts in winter
FlightsFlights
FlightsFlights

Chelmsford

Chelmsford

Cheap flights to Middlesex County from $53 One Way, $117 Round Trip

$117 return flights and $53 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 30 - Sat, Feb 6
MCO
Orlando
PSM
Portsmouth
$117 Roundtrip, found 2 days ago
$117
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Jan 30 from Orlando to Portsmouth, returning Sat, Feb 6, priced at $117 found 2 days ago
Sat, Jan 30 - Sat, Feb 6
MCO
Orlando
PSM
Portsmouth
$122 Roundtrip, found 2 days ago
$122
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Jan 30 from Orlando to Portsmouth, returning Sat, Feb 6, priced at $122 found 2 days ago
Thu, Oct 22 - Sat, Oct 24
MCO
Orlando
BOS
Boston
$138 Roundtrip, found 2 days ago
$138
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Oct 22 from Orlando to Boston, returning Sat, Oct 24, priced at $138 found 2 days ago
Tue, Aug 18 - Sun, Aug 30
FLL
Fort Lauderdale
BOS
Boston
$162 Roundtrip, found 1 day ago
$162
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 18 from Fort Lauderdale to Boston, returning Sun, Aug 30, priced at $162 found 1 day ago
Wed, Sep 16 - Tue, Sep 22
FLL
Fort Lauderdale
BOS
Boston
$167 Roundtrip, found 4 hours ago
$167
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, Sep 16 from Fort Lauderdale to Boston, returning Tue, Sep 22, priced at $167 found 4 hours ago
Wed, Sep 2 - Sun, Sep 6
MCO
Orlando
MHT
Manchester
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Sep 2 from Orlando to Manchester, returning Sun, Sep 6, priced at $169 found 1 day ago
Wed, Sep 23 - Sun, Sep 27
FLL
Fort Lauderdale
BOS
Boston
$172 Roundtrip, found 1 day ago
$172
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 23 from Fort Lauderdale to Boston, returning Sun, Sep 27, priced at $172 found 1 day ago
Wed, Sep 16 - Tue, Sep 22
FLL
Fort Lauderdale
BOS
Boston
$177 Roundtrip, found 4 hours ago
$177
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, Sep 16 from Fort Lauderdale to Boston, returning Tue, Sep 22, priced at $177 found 4 hours ago
Thu, Aug 27 - Wed, Sep 2
MCO
Orlando
PVD
Providence
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Aug 27 from Orlando to Providence, returning Wed, Sep 2, priced at $177 found 1 day ago
Wed, Sep 16 - Tue, Sep 22
FLL
Fort Lauderdale
BOS
Boston
$187 Roundtrip, found 4 hours ago
$187
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Sep 16 from Fort Lauderdale to Boston, returning Tue, Sep 22, priced at $187 found 4 hours ago
Wed, Sep 2 - Wed, Sep 23
FLL
Fort Lauderdale
PVD
Providence
$188 Roundtrip, found 4 hours ago
$188
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Sep 2 from Fort Lauderdale to Providence, returning Wed, Sep 23, priced at $188 found 4 hours ago
Wed, Sep 2 - Wed, Sep 9
MCO
Orlando
BOS
Boston
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 2 from Orlando to Boston, returning Wed, Sep 9, priced at $197 found 1 day ago

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
$161 nightly
The price is $187 total per night from Jul 5 to Jul 6
$187 total
Jul 5 - Jul 6
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! (2,373 reviews)
"Location and quality of property, services and staff."

Reviewed on Jun 16, 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
$305 nightly
The price is $341 total per night from Jun 30 to Jul 1
$341 total
Jun 30 - Jul 1
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! (3,875 reviews)
"Helpful staff, very clean room and casino was close."

Reviewed on Jun 16, 2026

Opens in a new windowEncore Boston Harbor
Hampton Inn & Suites Boston/Waltham

Hampton Inn & Suites Boston/Waltham

3 out of 5
135 2nd Ave Waltham MA
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $136 total per night from Jul 4 to Jul 5
$136 total
Jul 4 - Jul 5
Total with taxes and fees
Book a stay at this business-friendly hotel in Waltham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.4/10 Exceptional! (1,917 reviews)
"Le déjeuner était très bien. Les chambres propres."

Reviewed on Jun 13, 2026

Opens in a new windowHampton Inn & Suites Boston/Waltham
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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
$116 nightly
The price is $130 total per night from Jul 13 to Jul 14
$130 total
Jul 13 - Jul 14
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 ...
8.8/10 Excellent! (1,074 reviews)
"The room we were originally given was not cleaned and was moved to another room. We were given breakfast vouchers but when we tried to use them was told we didn't use it in the time allotted. The room was nice but had no drawers, anywhere. Front staff on the weekend was wonderful, Christian and Bob. ..."

Reviewed on Jun 16, 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

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

Orbitz provides convenient, one-stop shopping for travelers looking for budget flights to Middlesex County or any other low fare domestic or international air travel.

Innovative Orbitz Tools for the Trip Planner on the Move

Now it is even faster to find exclusive deals and book cheap Middlesex County flights from any location with our new Orbitz apps. These cutting-edge mobile tools are available free to anyone with an Android device, iPad, or iPhone. Look up Middlesex County's most popular attractions, best restaurants, and entertainment venues or check on your flights to Middlesex County and make changes to your itinerary while waiting in line for your latte.

Stay on Budget, Earn Miles with Bargain Middlesex County Flights

You can find amazing discount fares with Orbitz’s guaranteed low prices or take advantage of last-minute sales and special travel packages. You can also earn points towards your airline frequent flyer programs when you book qualified flights to Middlesex County. That means you can rack up money-saving points and miles for future use while saving money now.

We Are Just a Phone Call Away If You Need Us

Booking, changing, or canceling your Middlesex County flights is a breeze with Orbitz’s online and mobile tools, but that doesn't mean that we leave you hanging if you want to speak with one of our representatives. If you need help, just contact our Customer Service by email or phone. To enjoy a less stressful trip, be sure to sign up for instant alerts so we can send you any updates or delays relating to your flights to Middlesex County to your mobile phone or email.

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 $197 for a return trip to Middlesex County. One-way flights departing from Orlando (MCO) dropped down to $53 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.