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.

Wed, Sep 30 - Wed, Oct 7
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$96 Roundtrip, found 2 days ago
$96
Roundtrip
found 2 days 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 2 days ago
Wed, Aug 26 - Wed, Sep 2
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 Wed, Aug 26 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Sep 2, priced at $98 found 1 day ago
Sat, Sep 5 - Tue, Sep 8
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$102 Roundtrip, found 2 days ago
$102
Roundtrip
found 2 days 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 2 days ago
Wed, Aug 26 - Sat, Aug 29
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$109 Roundtrip, found 15 hours ago
$109
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Wed, Aug 26 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 29, priced at $109 found 15 hours ago
Wed, Aug 12 - Wed, Aug 19
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$112 Roundtrip, found 9 hours ago
$112
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Aug 12 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Aug 19, priced at $112 found 9 hours ago
Wed, Sep 16 - Wed, Sep 23
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 Wed, Sep 16 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Sep 23, priced at $114 found 2 days ago
Tue, Sep 1 - Sat, Sep 5
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$114 Roundtrip, just found
$114
Roundtrip
just found
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Sep 5, priced at $114 just found
Fri, Aug 28 - Tue, Sep 1
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$116 Roundtrip, found 6 days ago
$116
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Aug 28 from Tampa Intl. to Tweed - New Haven Regional, returning Tue, Sep 1, priced at $116 found 6 days ago
Wed, Aug 26 - Wed, Sep 2
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$116 Roundtrip, found 1 day ago
$116
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Wed, Aug 26 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Sep 2, priced at $116 found 1 day ago
OriginDestinationTravel DatesFlights From*
MCOEast HavenSeptember 16 to September 23$96
ORDEast HavenAugust 20 to August 23$118
MCOWindsor LocksSeptember 10 to September 14$118
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$159
CLTWindsor LocksOctober 20 to October 24$177
SJUEast HavenAugust 22 to August 26$199
DCAWindsor LocksAugust 11 to August 18$200
ATLWindsor LocksAugust 8 to August 15$203
SJUWindsor LocksOctober 14 to October 21$218
LAXWindsor LocksAugust 23 to September 6$226
DENWindsor LocksSeptember 9 to September 15$295
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
FLLEast HavenJuly 10 to August 17$226
MCOEast HavenJuly 11 to July 21$242
MCOWindsor LocksJuly 11 to July 18$280
ATLEast HavenJuly 10 to July 23$307
FLLWindsor LocksJuly 11 to July 13$325
TPAWindsor LocksJuly 12 to July 15$365
ORDWindsor LocksJuly 11 to July 18$374
DCAWindsor LocksJuly 11 to July 14$384
TPAEast HavenJuly 11 to July 12$385
SJUWindsor LocksJuly 12 to July 27$397
CLTWindsor LocksJuly 11 to July 12$421
SJUEast HavenJuly 11 to August 10$425
ATLWindsor LocksJuly 10 to July 14$480
DENWindsor LocksJuly 12 to July 15$490
LAXWindsor LocksJuly 10 to August 7$512
*Prices include taxes and fees

Best Middlesex County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex
2.0-star property

Pier Blue Inn Old Saybrook - Essex

Sep 3 - Sep 7

4 night stay

Atlanta (ATL) to New Haven (HVN)

Xtra Airways • Roundtrip • Coach
Save 100% on your flight
Price was $610, price is now $457 per person
$457
per person
found 7 hours ago
Hyatus Luxury Residences City Crossing
4.0-star property

Hyatus Luxury Residences City Crossing

Aug 27 - Aug 31

4 night stay

Raleigh (RDU) to New Haven (HVN)

Xtra Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,045, price is now $790 per person
$790
per person
found 7 hours ago
Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5-star property

Luxury Furnished Apartments by Hyatus Downtown at Yale

Aug 27 - Aug 31

4 night stay

Raleigh (RDU) to New Haven (HVN)

Xtra Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,071, price is now $818 per person
$818
per person
found 7 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! (1,009 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
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
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! (606 reviews)
"Great location.Family Oriented atmosphere. Friendly Staff"

Reviewed on Jul 7, 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 $96. 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 16 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, September 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 $96 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 $96 and $512. 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.