Cheap Flights to Essex County from $51 (2026/2027)

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Gloucester

Flights
Gloucester

How Much Does it Cost To Fly To Essex County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Oct 31 - Sat, Oct 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 31, priced at $112 found 1 day ago
Sat, Oct 3 - Wed, Oct 7
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$117 Roundtrip, just found
$117
Roundtrip
just found
Select American Airlines flight, departing Sat, Oct 3 from Ronald Reagan Washington National to Logan Intl., returning Wed, Oct 7, priced at $117 just found
Sat, Oct 31 - Sat, Oct 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 3 days ago
$122
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 31, priced at $122 found 3 days ago
Sat, Oct 31 - Sat, Nov 7
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 7, priced at $127 found 1 day ago
Sat, Oct 31 - Sun, Nov 8
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando Intl. to Portsmouth Intl., returning Sun, Nov 8, priced at $127 found 2 days ago
Sat, Oct 31 - Sat, Oct 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$132 Roundtrip, found 19 hours ago
$132
Roundtrip
found 19 hours ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 31, priced at $132 found 19 hours ago
Wed, Oct 28 - Sat, Oct 31
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$155 Roundtrip, found 5 days ago
$155
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Oct 28 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Oct 31, priced at $155 found 5 days ago
Wed, Dec 2 - Sat, Dec 5
RSW
Southwest Florida Intl.
PSM
Portsmouth Intl.
$163 Roundtrip, found 2 days ago
$163
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Dec 2 from Southwest Florida Intl. to Portsmouth Intl., returning Sat, Dec 5, priced at $163 found 2 days ago
Sat, Oct 3 - Wed, Oct 7
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$171 Roundtrip, just found
$171
Roundtrip
just found
Select United flight, departing Sat, Oct 3 from Ronald Reagan Washington National to Logan Intl., returning Wed, Oct 7, priced at $171 just found
Sat, Dec 5 - Sat, Dec 12
RSW
Southwest Florida Intl.
MHT
Manchester-Boston Regional
$178 Roundtrip, found 4 days ago
$178
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Dec 5 from Southwest Florida Intl. to Manchester-Boston Regional, returning Sat, Dec 12, priced at $178 found 4 days ago
Wed, Oct 14 - Tue, Oct 20
DCA
Ronald Reagan Washington National
MHT
Manchester-Boston Regional
$196 Roundtrip, found 4 days ago
$196
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Oct 14 from Ronald Reagan Washington National to Manchester-Boston Regional, returning Tue, Oct 20, priced at $196 found 4 days ago

Best Essex County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Wylie Inn and Conference Center at Endicott College
3.5-star property

The Wylie Inn and Conference Center at Endicott College

Sep 29 - Oct 2

3 night stay

Charlotte (CLT) to Boston (BOS)

Delta • Roundtrip • Coach
Price was $1,128, price is now $725 per person
$725
per person
found 1 day ago
Boston Lodge and Suites
4.0-star property

Boston Lodge and Suites

Nov 15 - Nov 19

4 night stay

Charlotte (CLT) to Boston (BOS)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,587, price is now $762 per person
$762
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Oct 9 - Oct 14

5 night stay

Charlotte (CLT) to Boston (BOS)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $3,556, price is now $2,239 per person
$2,239
per person
found 1 day ago
Don't see what you're looking for?
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Travelers ❤️ These Essex County 🏨

DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
50 Ferncroft Rd Danvers MA
Book a stay at this golf hotel in Danvers. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Water Park of New England and Glen Magna Farms are located nearby.
8.2/10 Very Good! (2,549 reviews)
"Was told I could check in early and then when I arrived I was told there was nothing available, had to wait around for 4 hours. Rooms smelled funny, fridge didn’t keep food cold, toilet wouldn’t flush. Arcade and pool hours closed early. The waterpark part was great, staff there were great and very ..."

Reviewed on Aug 25, 2026

Opens in a new windowDoubleTree by Hilton Boston North Shore
Holiday Inn Hotel & Suites Boston - Peabody by IHG

Holiday Inn Hotel & Suites Boston - Peabody by IHG

3 out of 5
1 Newbury St Peabody MA
Book a stay at this business-friendly hotel in Peabody. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Salem Witch Museum and Salem Common are located nearby.
Opens in a new windowHoliday Inn Hotel & Suites Boston - Peabody by IHG
Sonesta Select Boston Danvers

Sonesta Select Boston Danvers

3 out of 5
275 Independence Way Danvers MA
Book a stay at this business-friendly hotel in Danvers. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Salem Witch Museum and Salem Common are located nearby.
8.6/10 Excellent! (1,099 reviews)
"The staff was extremely helpful, but the facility is in bad need of updating (i.e. The sofa and our room was ripped)."

Reviewed on Aug 24, 2026

Opens in a new windowSonesta Select Boston Danvers
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Holiday Inn Express Boston - Saugus by IHG

Holiday Inn Express Boston - Saugus by IHG

3 out of 5
999 Broadway Saugus MA
Book a stay at this business-friendly hotel in Saugus. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Encore Boston Harbor and Revere Beach are located nearby.
8.6/10 Excellent! (1,204 reviews)
"Staff was friendly"

Reviewed on Aug 23, 2026

Opens in a new windowHoliday Inn Express Boston - Saugus by IHG
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 Essex County?
To give you an idea of prices, the cheapest roundtrip flight to Essex County was $112 during the last seven days. A great way to bag a travel bargain is to be flexible with your dates. This price was available on Travelocity for flights to Essex County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Essex County?
Put together your itinerary and then jet away with one of the 20 airlines that fly to Essex County. Consider booking a seat with the popular air carrier, American Airlines. It offers around 325 flights every month to Haverhill, Essex County's gateway city, so finding your perfect fare should be a cinch.
What is the cheapest month to fly to Essex County?
Based on Travelocity's direct return flight demand from January to December last year, October is the cheapest period to fly to Essex County. Search for flights during this month and get a top deal today.
How can I check my flight status to Essex County?
"Trips" can fill you in when it comes to information about your flight to Essex County. This handy portal allows you to manage everything in the one place, from checking your flight status to making changes to your itinerary. Click on Trips at the top right of the Travelocity homepage and then sign in or create an account. You can also download the Travelocity app and access your information while you're out and about. Whether you've got the family flying with you or you're wandering on your own, all your travel plans are right at your fingertips.
How do I find the best deals on flights to Essex County?
Here are some tips — book in advance, avoid vacation periods and be flexible with your travel dates. If your dates aren't set in stone, search for your flight to Essex County on Travelocity and click on "Flexible dates" at the top of the page. This will show you any cheaper tickets on a nearby day. $112 was the lowest price paid for a return flight to Essex County in the last seven days. 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 Essex County with Travelocity?
Start packing today and prepare to jet off with Travelocity. It's our job to find you fantastic deals on cheap flights to Essex County. Whether you're looking for airfares with flexible cancellation policies or cheap family flights from budget carriers, we can make it happen.
What are the most popular flight routes to Essex County?
As a leading destination for travelers, it's easy to find flights to Essex County. Browse this list of popular routes:

  • Chicago, IL (ORD-O'Hare Intl.) to Logan Intl. Airport (BOS) - 3,514 flights a month.
  • Washington, DC (DCA-Ronald Reagan Washington National) to Logan Intl. Airport (BOS) - 3,419 flights a month.
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Logan Intl. Airport (BOS) - 3,193 flights a month.

How much is a flight to Essex County on average?
Roundtrip flights to Essex County cost between $112 and $196 in the last seven days. When you find a price that works for you, grab it fast. Cheap deals don't hang around forever! These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Essex County?
Here are a number of preferred direct flights to Essex County plus their average journey times:

  • Chicago, IL (ORD-O'Hare Intl.) to Logan Intl. Airport (BOS) - 2 hours and 23 minutes
  • Washington, DC (DCA-Ronald Reagan Washington National) to Logan Intl. Airport (BOS) - 1 hour and 51 minutes
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Logan Intl. Airport (BOS) - 2 hours and 56 minutes

What can I expect on a flight to Essex County?
This mostly depends on your carrier and the duration of your flight. Many airlines provide warm meals, snacks and entertainment on long-haul journeys. Whether you're chasing business class flights to Essex County or cheap flights for family vacations, you'll be well looked after from takeoff to touchdown.