Flights To Middlesex County - Cheap Flights Starting at CA $73

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A rocky beach with large boulders and the ocean in the background.

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.

Tue, Aug 4 - Wed, Aug 5
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $162 Roundtrip, found 13 hours ago
CA $162
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Tue, Aug 4 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Aug 5, priced at CA $162 found 13 hours ago
Thu, Oct 1 - Sun, Oct 4
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $173 Roundtrip, found 19 hours ago
CA $173
Roundtrip
found 19 hours ago
Select Breeze Airways flight, departing Thu, Oct 1 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Oct 4, priced at CA $173 found 19 hours ago
Thu, Aug 27 - Mon, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $178 Roundtrip, found 6 days ago
CA $178
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Aug 27 from Orlando Intl. to Bradley Intl., returning Mon, Aug 31, priced at CA $178 found 6 days ago
Tue, Aug 4 - Wed, Aug 5
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $184 Roundtrip, found 13 hours ago
CA $184
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Tue, Aug 4 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Aug 5, priced at CA $184 found 13 hours ago
Tue, Aug 4 - Thu, Aug 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $203 Roundtrip, found 3 days ago
CA $203
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Aug 4 from Orlando Intl. to Tweed - New Haven Regional, returning Thu, Aug 6, priced at CA $203 found 3 days ago
Fri, Sep 4 - Mon, Sep 7
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $209 Roundtrip, found 6 days ago
CA $209
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Sep 4 from Orlando Intl. to Bradley Intl., returning Mon, Sep 7, priced at CA $209 found 6 days ago
Tue, Aug 4 - Thu, Aug 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $227 Roundtrip, found 13 hours ago
CA $227
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Tue, Aug 4 from Orlando Intl. to Tweed - New Haven Regional, returning Thu, Aug 6, priced at CA $227 found 13 hours ago
Wed, Oct 21 - Sat, Oct 24
MCO
Orlando Intl.
BDL
Bradley Intl.
CA $229 Roundtrip, found 5 days ago
CA $229
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Oct 21 from Orlando Intl. to Bradley Intl., returning Sat, Oct 24, priced at CA $229 found 5 days ago
Tue, Sep 1 - Tue, Sep 22
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $648 Roundtrip, found 19 hours ago
CA $648
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Tue, Sep 1 from Pearson Intl. to Bradley Intl., returning Tue, Sep 22, priced at CA $648 found 19 hours ago
Tue, Sep 1 - Tue, Sep 22
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $648 Roundtrip, found 19 hours ago
CA $648
Roundtrip
found 19 hours ago
Select Delta flight, departing Tue, Sep 1 from Pearson Intl. to Bradley Intl., returning Tue, Sep 22, priced at CA $648 found 19 hours ago
Sat, Jul 25 - Sat, Aug 1
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $732 Roundtrip, found 8 hours ago
CA $732
Roundtrip
found 8 hours ago
Select WestJet flight, departing Sat, Jul 25 from Pearson Intl. to Bradley Intl., returning Sat, Aug 1, priced at CA $732 found 8 hours ago
OriginDestinationTravel datesFlights from*
MCOEast HavenAugust 4 to August 5CA $162
ORDEast HavenAugust 28 to August 30CA $173
MCOWindsor LocksAugust 27 to August 31CA $178
TPAEast HavenSeptember 18 to September 20CA $220
ATLEast HavenSeptember 11 to September 13CA $235
TPAWindsor LocksSeptember 13 to September 17CA $274
ORDWindsor LocksSeptember 2 to September 30CA $285
FLLEast HavenAugust 1 to August 5CA $297
LAXWindsor LocksOctober 16 to October 20CA $361
DENWindsor LocksSeptember 10 to September 16CA $418
SJUWindsor LocksAugust 14 to August 19CA $486
SJUEast HavenAugust 14 to August 19CA $491
ATLWindsor LocksJuly 31 to August 3CA $524
FLLWindsor LocksAugust 1 to August 9CA $549
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
ORDEast HavenJuly 10 to July 12CA $316
MCOWindsor LocksJuly 12 to July 13CA $449
ORDWindsor LocksJuly 11 to July 12CA $715
LAXWindsor LocksJuly 10 to July 12CA $1,467
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
New Haven Hotel
3.5-star property

New Haven Hotel

Oct 4 - Oct 8

4 night stay

Edmonton (YEG) to New Haven (HVN)

WestJet • Non-stop roundtrip • Coach
Price was CA $1,183, price is now CA $988 per person
CA $988
per person
found 17 hours ago
Pier Blue Inn Old Saybrook - Essex
2.0-star property

Pier Blue Inn Old Saybrook - Essex

Jul 25 - Aug 1

7 night stay

Toronto (YTO) to New Haven (HVN)

Air Canada • Roundtrip • Coach
Price was CA $1,451, price is now CA $1,119 per person
CA $1,119
per person
found 1 day ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Aug 3 - Aug 6

3 night stay

Calgary (YYC) to New Haven (HVN)

American Airlines • Non-stop roundtrip • Coach
Price was CA $2,267, price is now CA $1,920 per person
CA $1,920
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! (1,009 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! (604 reviews)
"Pictures are nothing like the actual rooms you'll be staying in. There was black mold growing on cheap tiled ceilings. The air conditioner wasn't working correctly and the whole room had a layer of moisture on everything including the worn down carpet and the bed sheets/pillows. The bathrooms are ..."

Reviewed on Jul 6, 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 CA $162. 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 $162 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 $162 and CA $1,467. 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.