Cheap Flights to Middlesex County from $48 (2026/2027)

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Beautiful sunrise at the mouth of the Connecticut River, Old Saybrook, Connecticut.

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, Jun 5 - Sat, Jun 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Fri, Jun 5 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Jun 6, priced at $98 found 1 day ago
Thu, Sep 17 - Sun, Sep 20
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Sep 17 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Sep 20, priced at $102 found 1 day ago
Thu, Sep 3 - Tue, Sep 8
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$107 Roundtrip, found 4 days ago
$107
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Tweed - New Haven Regional, returning Tue, Sep 8, priced at $107 found 4 days ago
Sat, Sep 5 - Sun, Sep 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$112 Roundtrip, found 11 hours ago
$112
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Sat, Sep 5 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Sep 13, priced at $112 found 11 hours ago
Thu, Sep 24 - Sat, Sep 26
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$114 Roundtrip, found 2 days ago
$114
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Thu, Sep 24 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Sep 26, priced at $114 found 2 days ago
Wed, Jun 3 - Sat, Jun 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$118 Roundtrip, found 1 hour ago
$118
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Wed, Jun 3 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Jun 6, priced at $118 found 1 hour ago
Tue, Jun 9 - Wed, Jun 10
MCO
Orlando Intl.
BDL
Bradley Intl.
$135 Roundtrip, found 21 hours ago
$135
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Tue, Jun 9 from Orlando Intl. to Bradley Intl., returning Wed, Jun 10, priced at $135 found 21 hours ago
Sat, Jun 6 - Wed, Jun 10
MCO
Orlando Intl.
BDL
Bradley Intl.
$137 Roundtrip, found 3 hours ago
$137
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Jun 6 from Orlando Intl. to Bradley Intl., returning Wed, Jun 10, priced at $137 found 3 hours ago
OriginDestinationTravel DatesFlights From*
MCOEast HavenSeptember 1 to September 8$117
TPAEast HavenAugust 26 to August 29$118
ORDEast HavenJune 12 to June 14$120
MCOWindsor LocksJune 9 to June 10$135
FLLEast HavenJune 6 to June 10$136
TPAWindsor LocksSeptember 2 to September 8$142
ATLEast HavenAugust 28 to August 31$157
FLLWindsor LocksAugust 21 to August 23$208
ATLWindsor LocksAugust 19 to August 24$214
LAXWindsor LocksSeptember 2 to September 6$232
DCAWindsor LocksJuly 7 to July 8$242
SJUWindsor LocksAugust 18 to August 31$278
DENWindsor LocksAugust 11 to August 18$303
SJUEast HavenAugust 21 to August 31$307
CLTWindsor LocksJune 24 to June 27$313
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
ORDEast HavenMay 29 to June 1$133
MCOEast HavenMay 30 to June 2$150
FLLEast HavenMay 29 to May 30$153
ATLEast HavenMay 29 to May 31$182
MCOWindsor LocksMay 30 to June 6$195
TPAEast HavenMay 29 to May 29$201
TPAWindsor LocksMay 31 to June 3$253
DCAWindsor LocksMay 31 to June 7$271
CLTWindsor LocksMay 30 to June 13$310
ATLWindsor LocksMay 29 to June 19$359
SJUWindsor LocksMay 29 to June 3$368
SJUEast HavenMay 29 to June 6$369
FLLWindsor LocksMay 31 to June 6$397
LAXWindsor LocksMay 29 to June 3$404
DENWindsor LocksMay 30 to June 1$473
*Prices include taxes and fees

Best Middlesex County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Landing Furnished Apartments near YSM
3.0-star property

Landing Furnished Apartments near YSM

May 27 - Jun 1

5 night stay

Nashville (BNA) to New Haven (HVN)

JetBlue Airways • Roundtrip • Coach
Price was $1,096, price is now $850 per person
$850
per person
found 1 day ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Aug 17 - Aug 21

4 night stay

Dallas (DFW) to New Haven (HVN)

American Airlines • Coach

New Haven (HVN) to Dallas (DFW)

Southwest Airlines • Coach
Save 100% on your flight
Price was $2,515, price is now $1,553 per person
$1,553
per person
found 1 day ago
Head of Pond House
3.0-star property

Head of Pond House

May 28 - Jun 1

4 night stay

Dallas (DFW) to New Haven (HVN)

Southwest Airlines • Non-stop • Coach

New Haven (HVN) to Dallas (DFW)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,750, price is now $1,290 per person
$1,290
per person
found 1 day ago
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See all available trips from Nashville to Middlesex County
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Travelers ❤️ These Middlesex County 🏨

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! (1,006 reviews)
"Bedding was suboptimal and toilets clogged. Additionally, very noisy due to 2 weddings in the resort that night… so not very relaxing."

Reviewed on May 17, 2026

Opens in a new windowWater's Edge Resort & Spa
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! (1,002 reviews)
"Comfortable for a nights stay. Close to nice restaurants and shopping."

Reviewed on May 21, 2026

Opens in a new windowPier Blue Inn Old Saybrook - Essex
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2 out of 5
298 E Haddam Moodus Rd East Haddam CT
Stay at this cabin in East Haddam. Enjoy free parking, patios, and climate control. Popular attractions Machimoodus State Park and Amasa Day House are located nearby.
9.6/10 Exceptional! (151 reviews)
"The most peaceful mothers day weekend ever"

Reviewed on May 16, 2026

Opens in a new windowPostcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Shubert Theater and Louis' Lunch are located nearby.
9.2/10 Wonderful! (2,133 reviews)
"If it was for the excellent staff...i would have found another place to stay. The air conditioning didnt work for all 3 days of our stay putting out over 80 plus air into our room. The maintenance man couldnt fix it and found a box fan and and an oscillating fan but that was all he had"

Reviewed on May 21, 2026

Opens in a new windowNew Haven 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 Middlesex County?
Based on prices found over the last seven days on Travelocity, a roundtrip flight to Middlesex County started at as little as $98. 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, June 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 $98 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 $98 and $473. 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.