Cheap Flights to Middlesex County from $57 (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, Feb 7
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$111 Roundtrip, found 1 day ago
$111
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jan 28 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Feb 7, priced at $111 found 1 day ago
Thu, Jan 28 - Sun, Jan 31
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$112 Roundtrip, found 19 hours ago
$112
Roundtrip
found 19 hours ago
Select Breeze Airways flight, departing Thu, Jan 28 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jan 31, priced at $112 found 19 hours ago
Thu, Jan 28 - Sun, Jan 31
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$117 Roundtrip, found 19 hours ago
$117
Roundtrip
found 19 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 19 hours ago
Fri, Dec 4 - Sun, Dec 6
MYR
Myrtle Beach Intl.
BDL
Bradley Intl.
$122 Roundtrip, just found
$122
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Dec 4 from Myrtle Beach Intl. to Bradley Intl., returning Sun, Dec 6, priced at $122 just found
Thu, Feb 25 - Sun, Feb 28
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$124 Roundtrip, found 6 days ago
$124
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Feb 25 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Feb 28, priced at $124 found 6 days ago
Thu, Jan 21 - Sun, Jan 24
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$125 Roundtrip, found 5 hours ago
$125
Roundtrip
found 5 hours 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 5 hours ago
Fri, Dec 11 - Mon, Dec 14
MYR
Myrtle Beach Intl.
HVN
Tweed - New Haven Regional
$125 Roundtrip, found 19 hours ago
$125
Roundtrip
found 19 hours ago
Select Avelo Airlines flight, departing Fri, Dec 11 from Myrtle Beach Intl. to Tweed - New Haven Regional, returning Mon, Dec 14, priced at $125 found 19 hours ago
Thu, Feb 4 - Sun, Feb 7
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$130 Roundtrip, found 1 day ago
$130
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Feb 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Feb 7, priced at $130 found 1 day ago
OriginDestinationTravel DatesFlights From*
FLLEast HavenNovember 13 to November 16$138
TPAEast HavenJanuary 8 to January 14$141
SJUEast HavenOctober 24 to October 26$159
MCOWindsor LocksNovember 4 to November 9$162
FLLWindsor LocksNovember 6 to November 9$166
MCOEast HavenDecember 10 to December 13$170
DCAWindsor LocksDecember 9 to December 12$177
TPAWindsor LocksJanuary 13 to January 17$183
SJUWindsor LocksNovember 6 to November 17$184
ORDEast HavenDecember 3 to December 6$204
ATLEast HavenDecember 3 to December 10$222
ATLWindsor LocksNovember 5 to November 9$236
LAXWindsor LocksOctober 28 to November 3$245
CLTWindsor LocksDecember 5 to December 12$288
DENWindsor LocksJanuary 7 to January 12$344
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
SJUEast HavenOctober 10 to October 12$205
FLLEast HavenOctober 10 to October 24$233
MCOEast HavenOctober 10 to October 20$247
ATLEast HavenOctober 10 to October 14$274
MCOWindsor LocksOctober 10 to October 15$317
SJUWindsor LocksOctober 9 to October 31$319
TPAEast HavenOctober 10 to October 23$344
CLTWindsor LocksOctober 10 to October 13$425
DCAWindsor LocksOctober 11 to November 5$438
ORDWindsor LocksOctober 9 to October 11$450
TPAWindsor LocksOctober 10 to October 17$451
FLLWindsor LocksOctober 11 to October 24$477
LAXWindsor LocksOctober 11 to December 12$541
ATLWindsor LocksOctober 10 to October 13$587
DENWindsor LocksOctober 11 to October 15$967
*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 30 - Jan 3

4 night stay

Orlando (MCO) to New Haven (HVN)

Breeze Airways • Non-stop • Coach

New Haven (HVN) to Orlando (MCO)

Frontier Airlines • Non-stop • Coach
Price was $1,330, price is now $1,058 per person
$1,058
per person
found 4 hours ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Dec 24 - Dec 27

3 night stay

Denver (DEN) to New Haven (HVN)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,456, price is now $1,335 per person
$1,335
per person
just found
Las Flores Villa
5.0-star property

Las Flores Villa

Dec 30 - Jan 3

4 night stay

Orlando (MCO) to New Haven (HVN)

Breeze Airways • Non-stop • Coach

New Haven (HVN) to Orlando (MCO)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $4,179, price is now $3,023 per person
$3,023
per person
found 4 hours ago
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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.
8/10 Very Good! (1,006 reviews)
"I would not recommend this property. Very expensive -244- for a smelly room, one small packet of shampoo, stained mattress pad."

Reviewed on Oct 4, 2026

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! (1,001 reviews)
"Scenery was picture postcard perfect! Highly recommend balcony view from the main hotel Room service was excellent and the dining room staff and food were wonderful Only downside. There were no robes in the room and if you drank the bottled water, you were charged. Not really disclosed very well ..."

Reviewed on Oct 5, 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.
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! (749 reviews)
"Property is beautiful. Very reasonable price Room is good and clean although I thought beds r kinda hard. Only negative thing is the tv reception. Goes out constantly, very annoying. Continental breakfast was good. Very convenient location. Next to Foxwoods and u can walk or take hotel shuttle to ..."

Reviewed on Oct 5, 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 $111. 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 15 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 $111 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 $111 and $967. 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.