Cheap Flights to Middlesex County from $43 (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.

Fri, Dec 4 - Mon, Dec 7
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$86 Roundtrip, found 3 hours ago
$86
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Dec 7, priced at $86 found 3 hours ago
Sat, Oct 3 - Mon, Oct 5
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$88 Roundtrip, found 10 hours ago
$88
Roundtrip
found 10 hours ago
Select Avelo Airlines flight, departing Sat, Oct 3 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Oct 5, priced at $88 found 10 hours ago
Thu, Aug 27 - Mon, Aug 31
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$90 Roundtrip, found 1 day ago
$90
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Thu, Aug 27 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Aug 31, priced at $90 found 1 day ago
Fri, Nov 6 - Mon, Nov 9
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$94 Roundtrip, found 22 hours ago
$94
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Fri, Nov 6 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Nov 9, priced at $94 found 22 hours ago
Wed, Oct 28 - Mon, Nov 2
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$94 Roundtrip, just found
$94
Roundtrip
just found
Select Avelo Airlines flight, departing Wed, Oct 28 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Nov 2, priced at $94 just found
Fri, Sep 11 - Mon, Sep 14
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$95 Roundtrip, found 22 hours ago
$95
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Fri, Sep 11 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Sep 14, priced at $95 found 22 hours ago
Thu, Dec 10 - Sun, Dec 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$100 Roundtrip, found 1 hour ago
$100
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Dec 10 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 13, priced at $100 found 1 hour ago
Sat, Sep 26 - Wed, Sep 30
RDU
Raleigh - Durham Intl.
BDL
Bradley Intl.
$112 Roundtrip, found 16 hours ago
$112
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Sat, Sep 26 from Raleigh - Durham Intl. to Bradley Intl., returning Wed, Sep 30, priced at $112 found 16 hours ago
Fri, Sep 11 - Mon, Sep 14
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$115 Roundtrip, found 16 hours ago
$115
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Fri, Sep 11 from Tampa Intl. to Tweed - New Haven Regional, returning Mon, Sep 14, priced at $115 found 16 hours ago
OriginDestinationTravel DatesFlights From*
MCOEast HavenOctober 3 to October 6$114
ORDEast HavenSeptember 9 to September 14$118
TPAEast HavenOctober 3 to October 5$119
FLLEast HavenSeptember 21 to September 28$134
ATLEast HavenOctober 15 to October 19$136
MCOWindsor LocksSeptember 10 to September 14$145
TPAWindsor LocksOctober 29 to November 4$147
FLLWindsor LocksSeptember 11 to September 16$154
SJUWindsor LocksOctober 5 to October 12$158
DCAWindsor LocksOctober 29 to October 31$177
SJUEast HavenSeptember 12 to September 16$199
ATLWindsor LocksOctober 30 to November 2$210
LAXWindsor LocksOctober 10 to October 12$242
DENWindsor LocksOctober 30 to November 5$268
CLTWindsor LocksSeptember 19 to September 27$271
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
ORDEast HavenAugust 28 to August 31$119
ATLEast HavenAugust 28 to August 31$149
TPAEast HavenAugust 29 to September 6$181
FLLEast HavenAugust 29 to September 5$207
FLLWindsor LocksAugust 29 to August 31$251
TPAWindsor LocksAugust 29 to August 30$255
MCOWindsor LocksAugust 28 to August 31$272
ORDWindsor LocksAugust 29 to August 31$299
CLTWindsor LocksAugust 28 to August 31$300
SJUWindsor LocksAugust 28 to August 30$302
ATLWindsor LocksAugust 29 to September 5$335
DCAWindsor LocksAugust 28 to August 31$354
DENWindsor LocksAugust 28 to August 31$434
SJUEast HavenAugust 28 to August 31$442
LAXWindsor LocksAugust 30 to August 31$472
*Prices include taxes and fees

Best Middlesex County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Scranton Seahorse Inn
3.0-star property

The Scranton Seahorse Inn

Sep 24 - Sep 28

4 night stay

Fort Lauderdale (FLL) to New Haven (HVN)

Xtra Airways • Roundtrip • Coach
Save 100% on your flight
Price was $943, price is now $663 per person
$663
per person
found 15 hours ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Oct 23 - Oct 25

2 night stay

Orlando (MCO) to New Haven (HVN)

Breeze Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,523, price is now $909 per person
$909
per person
found 22 hours ago
Las Flores Villa
5.0-star property

Las Flores Villa

Oct 23 - Oct 25

2 night stay

Orlando (MCO) to New Haven (HVN)

Breeze Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,619, price is now $2,713 per person
$2,713
per person
found 22 hours 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.
8/10 Very Good! (1,011 reviews)
"Clean and comfortable room. Very dated furniture."

Reviewed on Aug 19, 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.
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.
9.4/10 Exceptional! (181 reviews)
"Our second time at post card cabins and we really enjoy it. Our only complaint this time around is that we texted saying we didn’t need anything replenished and then someone showed up midday and loudly knocked on our cabin (after we had just fallen asleep for a nap) so that was unfortunate. Also ..."

Reviewed on Aug 17, 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 Grand Theater at Foxwoods Resort Casino are located nearby.
8.6/10 Excellent! (275 reviews)
"Breakfast was very good. Room was is clean but there were ants in the room. Pool smells chlorine so much. For b&b it is a good choice."

Reviewed on Aug 21, 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 $86. 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, December 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 $86 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 $86 and $472. 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.