Flights To Essex County - Cheap Flights Starting at CA $75

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Essex County's top cities

A beach with a lifeguard tower, waves, and a large house with a tower on a rocky shore.

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 29 - Sat, Sep 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
CA $206 Roundtrip, found 2 days ago
CA $206
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Aug 29 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 5, priced at CA $206 found 2 days ago
Thu, Oct 29 - Sat, Oct 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
CA $235 Roundtrip, found 12 hours ago
CA $235
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Thu, Oct 29 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 31, priced at CA $235 found 12 hours ago
Sat, Aug 29 - Sun, Aug 30
MCO
Orlando Intl.
PSM
Portsmouth Intl.
CA $260 Roundtrip, found 2 days ago
CA $260
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Aug 29 from Orlando Intl. to Portsmouth Intl., returning Sun, Aug 30, priced at CA $260 found 2 days ago
Thu, Oct 1 - Sun, Oct 4
MCO
Orlando Intl.
PSM
Portsmouth Intl.
CA $283 Roundtrip, found 1 day ago
CA $283
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Oct 1 from Orlando Intl. to Portsmouth Intl., returning Sun, Oct 4, priced at CA $283 found 1 day ago
Thu, Oct 1 - Sun, Oct 4
MCO
Orlando Intl.
PSM
Portsmouth Intl.
CA $287 Roundtrip, found 4 days ago
CA $287
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Oct 1 from Orlando Intl. to Portsmouth Intl., returning Sun, Oct 4, priced at CA $287 found 4 days ago
Thu, Oct 29 - Sat, Oct 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
CA $292 Roundtrip, found 12 hours ago
CA $292
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Thu, Oct 29 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 31, priced at CA $292 found 12 hours ago
Fri, Aug 21 - Sat, Aug 22
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $343 Roundtrip, found 6 days ago
CA $343
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Aug 21 from Pearson Intl. to Logan Intl., returning Sat, Aug 22, priced at CA $343 found 6 days ago
Wed, Sep 9 - Wed, Sep 16
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $345 Roundtrip, found 1 hour ago
CA $345
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Wed, Sep 9 from Pearson Intl. to Logan Intl., returning Wed, Sep 16, priced at CA $345 found 1 hour ago
Sun, Sep 27 - Sat, Oct 3
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
CA $347 Roundtrip, found 3 days ago
CA $347
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Sep 27 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Oct 3, priced at CA $347 found 3 days ago
Wed, Aug 26 - Sat, Aug 29
MCO
Orlando Intl.
BOS
Logan Intl.
CA $356 Roundtrip, found 6 days ago
CA $356
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Aug 26 from Orlando Intl. to Logan Intl., returning Sat, Aug 29, priced at CA $356 found 6 days ago
Sat, Aug 15 - Tue, Aug 18
YEG
Edmonton Intl.
BOS
Logan Intl.
CA $437 Roundtrip, found 10 hours ago
CA $437
Roundtrip
found 10 hours ago
Select WestJet flight, departing Sat, Aug 15 from Edmonton Intl. to Logan Intl., returning Tue, Aug 18, priced at CA $437 found 10 hours ago
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Aug 22 - Aug 25

3 night stay

Detroit (DTW) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Price was CA $2,110, price is now CA $1,419 per person
CA $1,419
per person
found 1 day ago
Four Seasons Hotel Boston
5.0-star property

Four Seasons Hotel Boston

Aug 3 - Aug 9

6 night stay

Toronto (YYZ) to Boston (BOS)

Air Canada • Non-stop roundtrip • Coach
Price was CA $5,399, price is now CA $3,655 per person
CA $3,655
per person
found 15 hours ago
Good Hotels Boston
2.0-star property

Good Hotels Boston

Sep 18 - Sep 21

3 night stay

Edmonton (YEG) to Boston (BOS)

Porter Airlines • Non-stop roundtrip • Coach
Price was CA $2,054, price is now CA $1,468 per person
CA $1,468
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Detroit to Essex County
View all trips

Travelers ❤️ These Essex County 🏨

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.
9/10 Wonderful! (1,000 reviews)
"Nice and clean."

Reviewed on Jul 13, 2026

Opens in a new windowBest Western Plus North Shore Hotel
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.
8.2/10 Very good! (2,435 reviews)
"Someone stole my wife clothes for our room and manager is not helpful we need our money refunded"

Reviewed on Jul 16, 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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
La Quinta Inn & Suites by Wyndham Boston-Andover

La Quinta Inn & Suites by Wyndham Boston-Andover

3 out of 5
131 River Rd Andover MA
Book a stay at this business-friendly hotel in Andover. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Methuen Memorial Music Hall and Strike of 1912 Memorial are located nearby.
Opens in a new windowLa Quinta Inn & Suites by Wyndham Boston-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.

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 CA $206 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. CA $206 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 CA $206 and CA $437 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.