Flights To Middlesex County - Cheap Flights Starting at CA $116

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 Middlesex County's top cities

A rocky beach with large boulders and the ocean in the background.

Old Saybrook

Flights
Old Saybrook

How Much Does it Cost To Fly To Middlesex County?

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

Fri, Oct 30 - Mon, Nov 2
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $259 Roundtrip, found 1 day ago
CA $259
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Oct 30 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Nov 2, priced at CA $259 found 1 day ago
Sat, Jan 23 - Wed, Jan 27
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $261 Roundtrip, found 2 days ago
CA $261
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Jan 23 from Orlando Intl. to Bradley Intl., returning Wed, Jan 27, priced at CA $261 found 2 days ago
Fri, Oct 30 - Mon, Nov 2
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $278 Roundtrip, found 1 day ago
CA $278
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Oct 30 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Nov 2, priced at CA $278 found 1 day ago
Sat, Jan 23 - Wed, Jan 27
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $288 Roundtrip, found 2 days ago
CA $288
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Jan 23 from Orlando Intl. to Bradley Intl., returning Wed, Jan 27, priced at CA $288 found 2 days ago
Tue, Nov 3 - Wed, Nov 4
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $289 Roundtrip, found 3 days ago
CA $289
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Nov 3 from Orlando Intl. to Bradley Intl., returning Wed, Nov 4, priced at CA $289 found 3 days ago
Fri, Jan 15 - Mon, Jan 18
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $305 Roundtrip, found 2 days ago
CA $305
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jan 15 from Orlando Intl. to Bradley Intl., returning Mon, Jan 18, priced at CA $305 found 2 days ago
Fri, Oct 30 - Tue, Nov 3
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $351 Roundtrip, found 1 day ago
CA $351
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Fri, Oct 30 from Orlando Intl. to Tweed - New Haven Regional, returning Tue, Nov 3, priced at CA $351 found 1 day ago
Mon, Nov 23 - Tue, Nov 24
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $415 Roundtrip, found 21 hours ago
CA $415
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Mon, Nov 23 from Orlando Intl. to Bradley Intl., returning Tue, Nov 24, priced at CA $415 found 21 hours ago
Tue, Oct 20 - Tue, Oct 27
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $672 Roundtrip, found 2 days ago
CA $672
Roundtrip
found 2 days ago
Select United flight, departing Tue, Oct 20 from Pearson Intl. to Bradley Intl., returning Tue, Oct 27, priced at CA $672 found 2 days ago
Tue, Oct 20 - Tue, Oct 27
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $672 Roundtrip, found 2 days ago
CA $672
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Oct 20 from Pearson Intl. to Bradley Intl., returning Tue, Oct 27, priced at CA $672 found 2 days ago
Tue, Oct 20 - Tue, Oct 27
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $672 Roundtrip, found 2 days ago
CA $672
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Oct 20 from Pearson Intl. to Bradley Intl., returning Tue, Oct 27, priced at CA $672 found 2 days ago
OriginDestinationTravel datesFlights from*
FLLWindsor LocksNovember 12 to November 16CA $259
MCOEast HavenOctober 23 to October 26CA $260
SJUWindsor LocksOctober 23 to October 26CA $282
TPAWindsor LocksOctober 28 to October 31CA $286
MCOWindsor LocksNovember 3 to November 4CA $289
SJUEast HavenNovember 20 to November 28CA $306
ATLEast HavenDecember 7 to December 10CA $325
ORDEast HavenOctober 30 to November 1CA $330
FLLEast HavenDecember 23 to December 30CA $343
TPAEast HavenOctober 30 to November 1CA $369
LAXWindsor LocksOctober 24 to October 30CA $504
DENWindsor LocksOctober 24 to October 28CA $698
CLTWindsor LocksDecember 3 to December 7CA $814
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
FLLEast HavenOctober 17 to October 19CA $364
ATLEast HavenOctober 16 to October 19CA $368
TPAEast HavenOctober 17 to October 24CA $412
MCOEast HavenOctober 16 to October 19CA $448
MCOWindsor LocksOctober 17 to October 18CA $487
FLLWindsor LocksOctober 17 to October 19CA $489
SJUWindsor LocksOctober 17 to October 24CA $515
TPAWindsor LocksOctober 16 to October 18CA $670
LAXWindsor LocksOctober 16 to October 18CA $862
ATLWindsor LocksOctober 16 to October 18CA $1,360
*Prices include taxes and fees

Travelers ❤️ These Middlesex County 🏨

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chalker Beach and Crystal Lake Town Park are located nearby.
Opens in a new windowPier Blue Inn Old Saybrook - Essex
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Tanger Outlets and Westbrook Town Beach are located nearby.
8.8/10 Excellent! (1,007 reviews)
"We had a fantastic stay here. It was beautiful, clean and the staff was excellent. We will be back."

Reviewed on Oct 8, 2026

Opens in a new windowWater's Edge Resort & Spa
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
298 E Haddam Moodus Rd East Haddam CT
Stay at this cabin in East Haddam. Enjoy free parking and patios. Popular attractions Machimoodus State Park and Amasa Day House are located nearby.
9.4/10 Exceptional! (201 reviews)
"Great experience. Nice clean and quiet."

Reviewed on Oct 7, 2026

Opens in a new windowPostcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Two Trees Inn

Two Trees Inn

2.5 out of 5
240 Indiantown Rd Mashantucket CT
Book a stay at this business-friendly hotel in Mashantucket. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Foxwoods Resort Casino and Great Wolf Lodge Water Park are located nearby.
Opens in a new windowTwo Trees Inn
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 Middlesex County?
Based on prices found over the last seven days on Travelocity, a roundtrip flight to Middlesex County started at as little as CA $259. If you can be flexible with your dates, it makes it easy to snap up a great bargain. This price was available on Travelocity for flights to Middlesex County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Middlesex County?
There are 20 airline companies offering flights to Middlesex County. If you're organizing a journey to Old Saybrook, pick American Airlines. This top carrier operates around 654 flights per month to Middlesex County's main city.
What is the cheapest month to fly to Middlesex County?
Based on Travelocity's direct return flight demand from January to December last year, October is the cheapest period to jump on a plane to Middlesex County. Keep your eyes peeled for flights throughout this month and lock in a terrific deal today.
How can I check my flight status to Middlesex County?
"Trips" should be your first port of call when it comes to information related to your flight to Middlesex County. This handy portal lets you do everything from one place, from looking up your flight status to making changes to your booking. Click on Trips at the top right of the Travelocity homepage and then create a free account. You can also download the Travelocity app and access your itinerary while you're out and about. Whether you have the family flying with you or you're a lone adventurer, all your bookings are right there at your fingertips.
How do I find the best deals on flights to Middlesex County?
Being flexible with your dates is a simple way to land an awesome deal. Travelocity makes it a snap to find your ideal fare through the "Flexible dates" function. First, search for your flight to Middlesex County, then compare prices for surrounding dates by hitting the "Flexible dates" dropdown box above. Booking earlier and avoiding peak season are other things to consider. In the last seven days, the best price for a return flight to Middlesex County was CA $259 on our site. 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 Middlesex County with Travelocity?
Pack your suitcase and prepare for an amazing adventure with Travelocity. We'll help you track down great deals on cheap flights to Middlesex County. Whether you're seeking flexible airfares with plenty of room to move or cheap family flights from low-cost airlines, we'll make it happen.
What are the most popular flight routes to Middlesex County?
Take a look at these top flight routes to Middlesex County and start planning your next adventure:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Bradley Intl. Airport (BDL) - 1,131 flights a month.
  • Chicago, IL (ORD-O'Hare Intl.) to Bradley Intl. Airport (BDL) - 1,048 flights a month.
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Bradley Intl. Airport (BDL) - 866 flights a month.

How much is a flight to Middlesex County on average?
Get your next getaway off to a flying start by snapping up an awesome deal with Travelocity. In the last seven days, roundtrip flights to Middlesex County cost between CA $259 and CA $1,360. Browse our site and secure an airfare that matches your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.