Cheap Flights to Middlesex County from $61 (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 21 - Thu, Jan 28
MYR
Myrtle Beach Intl.
BDL
Bradley Intl.
$122 Roundtrip, found 2 hours ago
$122
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, Jan 21 from Myrtle Beach Intl. to Bradley Intl., returning Thu, Jan 28, priced at $122 found 2 hours ago
Mon, Dec 7 - Mon, Dec 14
MYR
Myrtle Beach Intl.
HVN
Tweed - New Haven Regional
$125 Roundtrip, found 3 hours ago
$125
Roundtrip
found 3 hours ago
Select Avelo Airlines flight, departing Mon, Dec 7 from Myrtle Beach Intl. to Tweed - New Haven Regional, returning Mon, Dec 14, priced at $125 found 3 hours ago
Thu, Dec 3 - Sun, Dec 6
MYR
Myrtle Beach Intl.
BDL
Bradley Intl.
$132 Roundtrip, found 4 days ago
$132
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Dec 3 from Myrtle Beach Intl. to Bradley Intl., returning Sun, Dec 6, priced at $132 found 4 days ago
Thu, Dec 3 - Sun, Dec 6
MYR
Myrtle Beach Intl.
BDL
Bradley Intl.
$142 Roundtrip, found 5 hours ago
$142
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Thu, Dec 3 from Myrtle Beach Intl. to Bradley Intl., returning Sun, Dec 6, priced at $142 found 5 hours ago
Fri, Dec 4 - Sun, Dec 6
MYR
Myrtle Beach Intl.
HVN
Tweed - New Haven Regional
$152 Roundtrip, found 6 hours ago
$152
Roundtrip
found 6 hours ago
Select Avelo Airlines flight, departing Fri, Dec 4 from Myrtle Beach Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $152 found 6 hours ago
Sat, Oct 17 - Fri, Dec 11
MYR
Myrtle Beach Intl.
BDL
Bradley Intl.
$160 Roundtrip, found 3 days ago
$160
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Oct 17 from Myrtle Beach Intl. to Bradley Intl., returning Fri, Dec 11, priced at $160 found 3 days ago
Sun, Feb 14 - Fri, Feb 19
MYR
Myrtle Beach Intl.
HVN
Tweed - New Haven Regional
$161 Roundtrip, found 1 day ago
$161
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Sun, Feb 14 from Myrtle Beach Intl. to Tweed - New Haven Regional, returning Fri, Feb 19, priced at $161 found 1 day ago
Wed, Nov 4 - Mon, Nov 9
MYR
Myrtle Beach Intl.
BDL
Bradley Intl.
$162 Roundtrip, found 2 hours ago
$162
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Wed, Nov 4 from Myrtle Beach Intl. to Bradley Intl., returning Mon, Nov 9, priced at $162 found 2 hours ago
OriginDestinationTravel DatesFlights From*
TPAEast HavenJanuary 8 to January 14$139
SJUEast HavenOctober 21 to October 28$159
FLLEast HavenNovember 2 to November 9$165
FLLWindsor LocksDecember 4 to December 6$167
MCOWindsor LocksJanuary 13 to January 20$168
MCOEast HavenNovember 12 to November 15$170
TPAWindsor LocksJanuary 13 to January 17$183
SJUWindsor LocksNovember 12 to November 16$193
DCAWindsor LocksDecember 4 to December 7$211
ATLEast HavenDecember 3 to December 10$222
ATLWindsor LocksDecember 10 to December 15$231
LAXWindsor LocksOctober 28 to November 3$245
ORDWindsor LocksDecember 14 to December 17$255
CLTWindsor LocksDecember 5 to December 7$268
DENWindsor LocksDecember 9 to December 15$319
*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
TPAEast HavenOctober 10 to October 23$344
MCOWindsor LocksOctober 11 to October 18$413
CLTWindsor LocksOctober 10 to October 13$425
DCAWindsor LocksOctober 11 to November 5$428
SJUWindsor LocksOctober 11 to October 15$447
TPAWindsor LocksOctober 10 to October 13$468
FLLWindsor LocksOctober 11 to October 24$477
ORDWindsor LocksOctober 10 to October 12$487
LAXWindsor LocksOctober 10 to October 12$598
ATLWindsor LocksOctober 10 to October 13$624
DENWindsor LocksOctober 10 to October 13$855
*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 1 day ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Dec 19 - Dec 25

6 night stay

Austin (AUS) to New Haven (HVN)

United • Roundtrip • Coach
Price was $4,651, price is now $2,272 per person
$2,272
per person
found 1 day ago
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 1 day 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! (1,000 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.
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.
9.4/10 Exceptional! (199 reviews)
"Very communicative and smooth booking, arrival, and departure process. The stay was amazing, will return again."

Reviewed on Oct 5, 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 Great Wolf Lodge Water Park are located nearby.
8.4/10 Very Good! (764 reviews)
"Expedia said it was convenient to Mystic. That is wrong. The Google map directions took us down a extremely curvy long road that was a 9 out of 10 difficulty level. We were driving it at night. It took well over 30 minutes to get there. Expedia must get paid a lot of money to recommend it as convenient ..."

Reviewed on Oct 6, 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 $122. 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 $122 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 $122 and $855. 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.