Cheap Flights to Essex County from $50 (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, Aug 8 - Sat, Aug 15
PIE
St. Petersburg-Clearwater Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 17 hours ago
$102
Roundtrip
found 17 hours ago
Select Allegiant Air flight, departing Sat, Aug 8 from St. Petersburg-Clearwater Intl. to Portsmouth Intl., returning Sat, Aug 15, priced at $102 found 17 hours ago
Sat, Jan 16 - Sat, Jan 23
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 5 hours ago
$117
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Sat, Jan 16 from Orlando Intl. to Portsmouth Intl., returning Sat, Jan 23, priced at $117 found 5 hours ago
Wed, Sep 16 - Sat, Sep 19
RSW
Southwest Florida Intl.
MHT
Manchester-Boston Regional
$127 Roundtrip, found 4 days ago
$127
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Sep 16 from Southwest Florida Intl. to Manchester-Boston Regional, returning Sat, Sep 19, priced at $127 found 4 days ago
Wed, Oct 21 - Tue, Oct 27
SFO
San Francisco Intl.
BOS
Logan Intl.
$265 Roundtrip, found 3 days ago
$265
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Oct 21 from San Francisco Intl. to Logan Intl., returning Tue, Oct 27, priced at $265 found 3 days ago
Tue, Oct 20 - Sat, Oct 31
SFO
San Francisco Intl.
BOS
Logan Intl.
$269 Roundtrip, found 2 hours ago
$269
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Tue, Oct 20 from San Francisco Intl. to Logan Intl., returning Sat, Oct 31, priced at $269 found 2 hours ago
Tue, Sep 15 - Tue, Oct 6
SFO
San Francisco Intl.
BOS
Logan Intl.
$274 Roundtrip, found 2 days ago
$274
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Sep 15 from San Francisco Intl. to Logan Intl., returning Tue, Oct 6, priced at $274 found 2 days ago
Tue, Sep 22 - Sat, Sep 26
SFO
San Francisco Intl.
BOS
Logan Intl.
$275 Roundtrip, found 2 days ago
$275
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Sep 22 from San Francisco Intl. to Logan Intl., returning Sat, Sep 26, priced at $275 found 2 days ago
Sun, Aug 16 - Sun, Aug 23
AUS
Austin-Bergstrom Intl.
BOS
Logan Intl.
$275 Roundtrip, found 1 hour ago
$275
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Aug 16 from Austin-Bergstrom Intl. to Logan Intl., returning Sun, Aug 23, priced at $275 found 1 hour ago
Tue, Aug 4 - Wed, Aug 26
SFO
San Francisco Intl.
BOS
Logan Intl.
$278 Roundtrip, found 6 days ago
$278
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Tue, Aug 4 from San Francisco Intl. to Logan Intl., returning Wed, Aug 26, priced at $278 found 6 days ago
Fri, Oct 16 - Mon, Oct 19
AUS
Austin-Bergstrom Intl.
BOS
Logan Intl.
$291 Roundtrip, just found
$291
Roundtrip
just found
Select JetBlue Airways flight, departing Fri, Oct 16 from Austin-Bergstrom Intl. to Logan Intl., returning Mon, Oct 19, priced at $291 just found
Thu, Aug 13 - Tue, Aug 18
AUS
Austin-Bergstrom Intl.
BOS
Logan Intl.
$298 Roundtrip, found 4 hours ago
$298
Roundtrip
found 4 hours ago
Select Delta flight, departing Thu, Aug 13 from Austin-Bergstrom Intl. to Logan Intl., returning Tue, Aug 18, priced at $298 found 4 hours ago

Best Essex County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
4.0-star property

Boston Lodge and Suites

Aug 10 - Aug 14

4 night stay

Chicago (ORD) to Boston (BOS)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,279, price is now $754 per person
$754
per person
found 7 hours ago
Four Seasons Hotel Boston
5.0-star property

Four Seasons Hotel Boston

Sep 30 - Oct 3

3 night stay

Atlanta (ATL) to Boston (BOS)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,524, price is now $1,454 per person
$1,454
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Aug 20 - Aug 24

4 night stay

Atlanta (ATL) to Boston (BOS)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,035, price is now $1,233 per person
$1,233
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Chicago to Essex County
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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, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Water Park of New England and Putnam House are located nearby.
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.
7.2/10 Good! (1,007 reviews)
"Peabody location does not have any kind of dining room/restaurant. Just a few snacks and drinks."

Reviewed on Jul 18, 2026

Opens in a new windowHoliday Inn Hotel & Suites Boston - Peabody by IHG
Best Western Plus North Shore Hotel

Best Western Plus North Shore Hotel

2.5 out of 5
50 Dayton St Danvers MA
Book a stay at this business-friendly hotel in Danvers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Salem Witch Museum and Salem Common are located nearby.
Opens in a new windowBest Western Plus North Shore Hotel
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Hawthorne Hotel

Hawthorne Hotel

3.5 out of 5
18 Washington Square W Salem MA
Book a stay at this historic hotel in Salem. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Salem Witch Museum and Salem Common are located nearby.
9.4/10 Exceptional! (1,585 reviews)
"Me and a friend have stayed here twice now."

Reviewed on Jul 17, 2026

Opens in a new windowHawthorne Hotel
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 $102 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, August 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. $102 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 $102 and $298 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.