Cheap Flights to Middlesex County from $61 (2026/2027)

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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.

Thu, Jan 28 - Sun, Jan 31
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$117 Roundtrip, found 17 hours ago
$117
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Thu, Jan 28 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jan 31, priced at $117 found 17 hours ago
Thu, Jan 28 - Sun, Feb 7
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$122 Roundtrip, found 5 days ago
$122
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jan 28 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Feb 7, priced at $122 found 5 days ago
Thu, Jan 21 - Sun, Jan 24
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$125 Roundtrip, found 3 days ago
$125
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jan 21 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jan 24, priced at $125 found 3 days ago
Thu, Jan 28 - Sun, Feb 7
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$127 Roundtrip, found 5 days ago
$127
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jan 28 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Feb 7, priced at $127 found 5 days ago
Sun, Jan 24 - Sun, Jan 31
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$130 Roundtrip, found 3 days ago
$130
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Jan 24 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jan 31, priced at $130 found 3 days ago
Thu, Jan 28 - Sun, Feb 7
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$132 Roundtrip, found 5 days ago
$132
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jan 28 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Feb 7, priced at $132 found 5 days ago
Fri, Nov 13 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$146 Roundtrip, found 18 hours ago
$146
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Fri, Nov 13 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Nov 16, priced at $146 found 18 hours ago
Thu, Jan 28 - Mon, Feb 1
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$148 Roundtrip, found 17 hours ago
$148
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Thu, Jan 28 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Feb 1, priced at $148 found 17 hours ago
Fri, Jan 29 - Mon, Feb 1
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$158 Roundtrip, found 7 hours ago
$158
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Fri, Jan 29 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Feb 1, priced at $158 found 7 hours ago
Wed, Dec 2 - Mon, Dec 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$162 Roundtrip, found 12 hours ago
$162
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, Dec 2 from Orlando Intl. to Bradley Intl., returning Mon, Dec 7, priced at $162 found 12 hours ago
OriginDestinationTravel DatesFlights From*
MCOEast HavenJanuary 21 to January 24$125
TPAEast HavenJanuary 7 to January 10$142
FLLEast HavenNovember 13 to November 16$146
SJUEast HavenOctober 28 to October 30$159
MCOWindsor LocksDecember 2 to December 7$162
SJUWindsor LocksNovember 6 to November 9$162
TPAWindsor LocksJanuary 22 to January 24$164
FLLWindsor LocksDecember 3 to December 6$171
DCAWindsor LocksNovember 23 to December 2$217
ATLEast HavenDecember 3 to December 16$222
ATLWindsor LocksNovember 10 to November 12$236
LAXWindsor LocksOctober 31 to November 7$243
ORDWindsor LocksDecember 15 to December 20$267
CLTWindsor LocksDecember 5 to December 7$268
DENWindsor LocksDecember 3 to December 7$333
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
SJUEast HavenOctober 16 to October 26$159
FLLEast HavenOctober 17 to October 24$199
ORDEast HavenOctober 16 to October 19$236
MCOEast HavenOctober 17 to October 21$249
ATLEast HavenOctober 16 to October 19$254
TPAEast HavenOctober 17 to October 19$269
SJUWindsor LocksOctober 16 to October 19$300
MCOWindsor LocksOctober 16 to October 19$328
TPAWindsor LocksOctober 17 to October 18$372
CLTWindsor LocksOctober 17 to October 20$425
FLLWindsor LocksOctober 17 to October 20$434
DCAWindsor LocksOctober 16 to October 20$474
LAXWindsor LocksOctober 17 to October 25$496
ATLWindsor LocksOctober 16 to October 18$515
DENWindsor LocksOctober 17 to October 21$801
*Prices include taxes and fees

Best Middlesex County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Landing Apartments New Haven Near Dixwell
3.0-star property

Landing Apartments New Haven Near Dixwell

Dec 24 - Dec 27

3 night stay

Orlando (MCO) to New Haven (HVN)

Breeze Airways • Roundtrip • Coach
Price was $840, price is now $694 per person
$694
per person
found 1 day ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Dec 24 - Dec 27

3 night stay

Orlando (MCO) to New Haven (HVN)

Breeze Airways • Roundtrip • Coach
Save 100% on your flight
Price was $2,255, price is now $1,193 per person
$1,193
per person
found 1 day ago
Hyatus Luxury Residences City Crossing
4.0-star property

Hyatus Luxury Residences City Crossing

Dec 24 - Dec 27

3 night stay

Orlando (MCO) to New Haven (HVN)

Breeze Airways • Roundtrip • Coach
Price was $964, price is now $791 per person
$791
per person
found 1 day ago
Don't see what you're looking for?
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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.
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
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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.
8.4/10 Very Good! (815 reviews)
"Comfortable and clean"

Reviewed on Oct 11, 2026

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 $117. 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 18 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, January 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 $117 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 $117 and $801. 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.
How long is the average flight to Middlesex County?
The length of your direct flight to Middlesex County largely depends on your place of origin. To give you an idea of what to expect, here are the average travel times for a handful of leading routes to Middlesex County:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 15 minutes
  • Chicago, IL (ORD-O'Hare Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 9 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Bradley Intl. Airport (BDL) - 1 hour and 12 minutes

What can I expect on a flight to Middlesex County?
The time your flight takes and whether you fly with a full-service or low-cost carrier will mostly determine this. If you're on the lookout for long-haul flights to Middlesex County, entertainment, food and drinks will be standard inclusions. Wondering about cheap flights for family vacations? Look up the fares from low-cost carriers. Typically, these airlines don't have as many inclusions, or you'll need to pay an extra fee for them.