Cheap Flights to Middlesex County from $59 (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, Sep 10 - Sun, Sep 13
ORD
O'Hare Intl.
HVN
Tweed - New Haven Regional
$118 Roundtrip, found 1 hour ago
$118
Roundtrip
found 1 hour ago
Select Avelo Airlines flight, departing Thu, Sep 10 from O'Hare Intl. to Tweed - New Haven Regional, returning Sun, Sep 13, priced at $118 found 1 hour ago
Thu, Aug 27 - Sun, Aug 30
ORD
O'Hare Intl.
HVN
Tweed - New Haven Regional
$120 Roundtrip, just found
$120
Roundtrip
just found
Select Avelo Airlines flight, departing Thu, Aug 27 from O'Hare Intl. to Tweed - New Haven Regional, returning Sun, Aug 30, priced at $120 just found
Mon, Aug 31 - Wed, Sep 2
ORD
O'Hare Intl.
HVN
Tweed - New Haven Regional
$130 Roundtrip, found 10 hours ago
$130
Roundtrip
found 10 hours ago
Select Avelo Airlines flight, departing Mon, Aug 31 from O'Hare Intl. to Tweed - New Haven Regional, returning Wed, Sep 2, priced at $130 found 10 hours ago
Wed, Sep 2 - Fri, Sep 4
ORD
O'Hare Intl.
HVN
Tweed - New Haven Regional
$133 Roundtrip, found 10 hours ago
$133
Roundtrip
found 10 hours ago
Select Avelo Airlines flight, departing Wed, Sep 2 from O'Hare Intl. to Tweed - New Haven Regional, returning Fri, Sep 4, priced at $133 found 10 hours ago
Fri, Aug 14 - Sun, Aug 23
ORD
O'Hare Intl.
HVN
Tweed - New Haven Regional
$137 Roundtrip, found 3 days ago
$137
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Fri, Aug 14 from O'Hare Intl. to Tweed - New Haven Regional, returning Sun, Aug 23, priced at $137 found 3 days ago
Fri, Sep 4 - Mon, Sep 7
ORD
O'Hare Intl.
HVN
Tweed - New Haven Regional
$140 Roundtrip, found 5 days ago
$140
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Fri, Sep 4 from O'Hare Intl. to Tweed - New Haven Regional, returning Mon, Sep 7, priced at $140 found 5 days ago
Fri, Sep 18 - Sat, Sep 19
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$152 Roundtrip, found 5 days ago
$152
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Fri, Sep 18 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sat, Sep 19, priced at $152 found 5 days ago
Fri, Oct 16 - Mon, Oct 19
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Oct 16 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Oct 19, priced at $157 found 2 days ago
OriginDestinationTravel DatesFlights From*
MCOEast HavenSeptember 16 to September 23$96
MCOWindsor LocksOctober 22 to October 26$110
ORDEast HavenAugust 20 to August 23$118
TPAEast HavenAugust 25 to August 31$120
ATLEast HavenSeptember 26 to October 4$136
TPAWindsor LocksSeptember 5 to September 9$142
FLLEast HavenSeptember 11 to September 14$154
FLLWindsor LocksSeptember 12 to September 16$165
DCAWindsor LocksAugust 12 to August 16$199
SJUEast HavenAugust 22 to August 26$199
ATLWindsor LocksSeptember 24 to September 28$200
SJUWindsor LocksSeptember 2 to September 6$206
CLTWindsor LocksOctober 20 to October 24$220
LAXWindsor LocksSeptember 5 to September 12$233
DENWindsor LocksSeptember 10 to September 16$295
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
ORDEast HavenJuly 17 to July 20$166
FLLEast HavenJuly 17 to July 20$223
TPAEast HavenJuly 18 to August 22$236
MCOWindsor LocksJuly 18 to July 25$248
ATLEast HavenJuly 17 to July 31$279
TPAWindsor LocksJuly 17 to July 24$307
DCAWindsor LocksJuly 17 to July 24$309
ORDWindsor LocksJuly 18 to July 24$312
MCOEast HavenJuly 18 to July 22$314
FLLWindsor LocksJuly 18 to July 26$321
SJUWindsor LocksJuly 19 to August 1$333
ATLWindsor LocksJuly 18 to July 20$368
CLTWindsor LocksJuly 18 to July 20$368
DENWindsor LocksJuly 18 to July 22$472
LAXWindsor LocksJuly 17 to July 22$561
*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 24 - Sep 27

3 night stay

Raleigh (RDU) to New Haven (HVN)

United • Roundtrip • Coach
Price was $596, price is now $439 per person
$439
per person
found 1 day ago
New Haven Hotel
3.5-star property

New Haven Hotel

Aug 6 - Aug 10

4 night stay

Norfolk (ORF) to New Haven (HVN)

Breeze Airways • Coach

New Haven (HVN) to Norfolk (ORF)

American Airlines • Coach
Price was $706, price is now $531 per person
$531
per person
found 1 day ago
Landing Apartments New Haven Near Dixwell
3.0-star property

Landing Apartments New Haven Near Dixwell

Sep 4 - Sep 7

3 night stay

Tampa (TPA) to New Haven (HVN)

Delta • Coach

New Haven (HVN) to Tampa (TPA)

JetBlue Airways • Coach
Price was $1,064, price is now $800 per person
$800
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! (1,013 reviews)
"The room was hot, and AC barely worked."

Reviewed on Jul 10, 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! (1,002 reviews)
"Our room was lovely however it was on the second floor of the building with no elevator. There were 14 steep steps that had to be climbed. My husband (84) had trouble doing this. We were not notified of the steps when we made our reservations. When I asked for a different room, I was told they were ..."

Reviewed on Jul 10, 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! (612 reviews)
"The room was clean. No issues."

Reviewed on Jul 10, 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 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, 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 $561. 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.