Cheap Flights to Middlesex County from $48 (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.

Sun, Jan 24 - Thu, Jan 28
ORD
O'Hare Intl.
HVN
Tweed - New Haven Regional
$78 Roundtrip, found 6 days ago
$78
Roundtrip
found 6 days ago
Select Avelo Airlines flight, departing Sun, Jan 24 from O'Hare Intl. to Tweed - New Haven Regional, returning Thu, Jan 28, priced at $78 found 6 days ago
Wed, Sep 30 - Wed, Oct 7
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$96 Roundtrip, found 1 day ago
$96
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Wed, Sep 30 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Oct 7, priced at $96 found 1 day ago
Wed, Aug 26 - Wed, Sep 2
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$98 Roundtrip, found 12 hours ago
$98
Roundtrip
found 12 hours ago
Select Avelo Airlines flight, departing Wed, Aug 26 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Sep 2, priced at $98 found 12 hours ago
Sat, Sep 5 - Tue, Sep 8
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 Sat, Sep 5 from Orlando Intl. to Tweed - New Haven Regional, returning Tue, Sep 8, priced at $102 found 1 day ago
Wed, Aug 12 - Wed, Aug 19
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$107 Roundtrip, found 22 hours ago
$107
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Wed, Aug 12 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Aug 19, priced at $107 found 22 hours ago
Wed, Aug 26 - Wed, Sep 2
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$109 Roundtrip, found 12 hours ago
$109
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, Aug 26 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Sep 2, priced at $109 found 12 hours ago
Thu, Jan 28 - Sun, Jan 31
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day 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 1 day ago
Wed, Sep 16 - Wed, Sep 23
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$114 Roundtrip, found 1 day ago
$114
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Wed, Sep 16 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Sep 23, priced at $114 found 1 day ago
OriginDestinationTravel DatesFlights From*
MCOEast HavenSeptember 16 to September 23$96
TPAEast HavenAugust 31 to August 31$120
FLLEast HavenSeptember 5 to September 12$135
ATLEast HavenSeptember 3 to September 6$136
TPAWindsor LocksSeptember 13 to September 19$145
FLLWindsor LocksSeptember 10 to September 16$163
MCOWindsor LocksAugust 27 to September 6$165
SJUEast HavenAugust 22 to August 26$199
DCAWindsor LocksAugust 11 to August 18$200
ORDWindsor LocksJuly 30 to August 11$212
ATLWindsor LocksAugust 12 to August 19$215
SJUWindsor LocksAugust 29 to September 2$218
LAXWindsor LocksSeptember 2 to September 6$220
CLTWindsor LocksAugust 8 to August 15$262
DENWindsor LocksSeptember 9 to September 15$295
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
ORDEast HavenJuly 10 to July 13$179
FLLEast HavenJuly 10 to August 17$226
MCOWindsor LocksJuly 10 to July 18$250
TPAEast HavenJuly 11 to July 16$266
ATLEast HavenJuly 10 to July 12$267
MCOEast HavenJuly 12 to July 15$317
FLLWindsor LocksJuly 11 to July 16$321
SJUWindsor LocksJuly 11 to July 31$360
CLTWindsor LocksJuly 12 to July 13$371
LAXWindsor LocksJuly 12 to August 6$376
TPAWindsor LocksJuly 10 to July 12$383
DCAWindsor LocksJuly 11 to July 14$384
SJUEast HavenJuly 11 to August 10$425
ATLWindsor LocksJuly 11 to July 14$490
DENWindsor LocksJuly 11 to July 17$490
*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

Aug 21 - Aug 24

3 night stay

Sarasota (SRQ) to New Haven (HVN)

Xtra Airways • Roundtrip • Coach
Price was $683, price is now $571 per person
$571
per person
found 10 hours ago
Hyatus Luxury Residences City Crossing
4.0-star property

Hyatus Luxury Residences City Crossing

Aug 21 - Aug 24

3 night stay

Sarasota (SRQ) to New Haven (HVN)

Xtra Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,227, price is now $967 per person
$967
per person
found 10 hours ago
Graduate by Hilton New Haven
4.0-star property

Graduate by Hilton New Haven

Aug 21 - Aug 24

3 night stay

Sarasota (SRQ) to New Haven (HVN)

Xtra Airways • Roundtrip • Coach
Price was $748, price is now $607 per person
$607
per person
found 10 hours ago
Don't see what you're looking for?
See all available trips from Sarasota 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! (1,000 reviews)
"Beautiful property. Sunday Brunch was excellent. Staff is friendly."

Reviewed on Jul 1, 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! (1,009 reviews)
"Lage room, Clean and comfortable bed. Bathroom could use updating and an elevated toilet seat. Staff very nice. Would stay again."

Reviewed on Jul 7, 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

2.5 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! (163 reviews)
"Amazing woodland views and privacy. My wife didn’t want to leave. Great place to leave the world behind and just relax."

Reviewed on Jul 6, 2026

Opens in a new windowPostcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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Best Western Mystic Hotel

Best Western Mystic Hotel

2.5 out of 5
48 Whitehall Ave Mystic CT
Book a stay at this business-friendly hotel in Mystic. Enjoy free parking, an outdoor pool, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Olde Mistick Village and Mystic Aquarium and Institute for Exploration are located nearby.
8.6/10 Excellent! (604 reviews)
"Pictures are nothing like the actual rooms you'll be staying in. There was black mold growing on cheap tiled ceilings. The air conditioner wasn't working correctly and the whole room had a layer of moisture on everything including the worn down carpet and the bed sheets/pillows. The bathrooms are ..."

Reviewed on Jul 6, 2026

Opens in a new windowBest Western Mystic 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 $78. 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 $78 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 $78 and $490. 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.