Flights To Middlesex County - Cheap Flights Starting at CA $82

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Beautiful sunrise at the mouth of the Connecticut River, Old Saybrook, Connecticut.

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, Aug 27 - Mon, Aug 31
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $164 Roundtrip, found 5 days ago
CA $164
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Thu, Aug 27 from Tampa Intl. to Tweed - New Haven Regional, returning Mon, Aug 31, priced at CA $164 found 5 days ago
Wed, Jul 1 - Mon, Aug 31
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $192 Roundtrip, found 9 hours ago
CA $192
Roundtrip
found 9 hours ago
Select Avelo Airlines flight, departing Wed, Jul 1 from Tampa Intl. to Tweed - New Haven Regional, returning Mon, Aug 31, priced at CA $192 found 9 hours ago
Thu, Jul 30 - Thu, Aug 6
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $209 Roundtrip, found 3 days ago
CA $209
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Thu, Jul 30 from Tampa Intl. to Tweed - New Haven Regional, returning Thu, Aug 6, priced at CA $209 found 3 days ago
Thu, Aug 6 - Sun, Aug 9
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $235 Roundtrip, found 1 day ago
CA $235
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Thu, Aug 6 from Tampa Intl. to Tweed - New Haven Regional, returning Sun, Aug 9, priced at CA $235 found 1 day ago
Mon, Jul 13 - Fri, Jul 17
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $239 Roundtrip, found 5 days ago
CA $239
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Mon, Jul 13 from Tampa Intl. to Tweed - New Haven Regional, returning Fri, Jul 17, priced at CA $239 found 5 days ago
Sat, Jul 4 - Sun, Jul 5
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $240 Roundtrip, found 19 hours ago
CA $240
Roundtrip
found 19 hours ago
Select Avelo Airlines flight, departing Sat, Jul 4 from Tampa Intl. to Tweed - New Haven Regional, returning Sun, Jul 5, priced at CA $240 found 19 hours ago
Sat, Jun 6 - Sun, Jun 7
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
CA $241 Roundtrip, found 1 day ago
CA $241
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Sat, Jun 6 from Tampa Intl. to Tweed - New Haven Regional, returning Sun, Jun 7, priced at CA $241 found 1 day ago
Sun, Sep 20 - Mon, Sep 28
TPA
Tampa Intl.
BDL
Bradley Intl.
CA $245 Roundtrip, found 3 days ago
CA $245
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Sep 20 from Tampa Intl. to Bradley Intl., returning Mon, Sep 28, priced at CA $245 found 3 days ago
Wed, Aug 12 - Wed, Aug 19
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $711 Roundtrip, found 2 days ago
CA $711
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Aug 12 from Pearson Intl. to Bradley Intl., returning Wed, Aug 19, priced at CA $711 found 2 days ago
Thu, Jun 18 - Thu, Jul 16
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $783 Roundtrip, found 1 day ago
CA $783
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Jun 18 from Pearson Intl. to Bradley Intl., returning Thu, Jul 16, priced at CA $783 found 1 day ago
Thu, Jun 18 - Thu, Jul 16
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $783 Roundtrip, found 1 day ago
CA $783
Roundtrip
found 1 day ago
Select United flight, departing Thu, Jun 18 from Pearson Intl. to Bradley Intl., returning Thu, Jul 16, priced at CA $783 found 1 day ago
OriginDestinationTravel datesFlights from*
MCOEast HavenSeptember 5 to September 13CA $154
TPAEast HavenAugust 27 to August 31CA $164
ORDEast HavenJune 12 to June 14CA $169
MCOWindsor LocksAugust 31 to September 1CA $193
TPAWindsor LocksAugust 19 to August 24CA $273
ATLEast HavenJune 25 to June 29CA $310
FLLWindsor LocksAugust 13 to August 22CA $353
FLLEast HavenJune 19 to June 28CA $372
LAXWindsor LocksAugust 27 to August 30CA $373
DCAWindsor LocksJune 8 to June 11CA $429
DENWindsor LocksAugust 12 to August 17CA $447
ORDWindsor LocksJuly 18 to July 20CA $513
ATLWindsor LocksJune 22 to July 6CA $811
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
ORDEast HavenMay 29 to June 1CA $187
FLLEast HavenMay 29 to June 1CA $234
MCOWindsor LocksMay 30 to June 6CA $246
MCOEast HavenMay 29 to May 31CA $310
TPAEast HavenMay 29 to May 31CA $383
TPAWindsor LocksMay 31 to June 4CA $384
LAXWindsor LocksMay 30 to June 1CA $593
ATLWindsor LocksMay 30 to June 6CA $1,180
*Prices include taxes and fees
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

Jul 9 - Jul 13

4 night stay

Toronto (YYZ) to New Haven (HVN)

Porter Airlines • Roundtrip • Coach
Price was CA $1,061, price is now CA $837 per person
CA $837
per person
found 1 day ago
Head of Pond House
3.0-star property

Head of Pond House

Jun 9 - Jun 16

7 night stay

Montreal (YUL) to New Haven (HVN)

Delta • Roundtrip • Coach
Price was CA $3,904, price is now CA $2,796 per person
CA $2,796
per person
found 20 hours ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Jun 27 - Jun 30

3 night stay

Montreal (YUL) to New Haven (HVN)

Porter Airlines • Roundtrip • Coach
Price was CA $2,889, price is now CA $2,118 per person
CA $2,118
per person
found 1 day ago
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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! (1,002 reviews)
"Nice location, well maintained grounds, the buildings are old, old bathrooms, not well controlled temperature in the guest rooms, some of the staff is not very welcoming."

Reviewed on May 23, 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! (1,008 reviews)
"The mold was seen visible in the bathroom and the floors were not clean. Old furniture and asked for a rebate to no avail. Was told the property was updated. Beds are old and furniture is not new. TV has very few stations. Was not satisfied at all."

Reviewed on May 25, 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 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! (154 reviews)
"Nature path"

Reviewed on May 23, 2026

Opens in a new windowPostcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Shubert Theater and White Space Gallery are located nearby.
9.2/10 Wonderful! (2,140 reviews)
"Easy check in. Super clean hotel. Friendly staff."

Reviewed on May 25, 2026

Opens in a new windowNew Haven 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 CA $154. 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 20 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, August 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 CA $154 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 CA $154 and CA $1,180. 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.