Flights To Middlesex County - Cheap Flights Starting at CA $384

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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.

Sat, Sep 26 - Tue, Sep 29
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $687 Roundtrip, found 1 day ago
CA $687
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Sep 26 from Pearson Intl. to Bradley Intl., returning Tue, Sep 29, priced at CA $687 found 1 day ago
Sat, Sep 26 - Tue, Sep 29
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $687 Roundtrip, found 1 day ago
CA $687
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 26 from Pearson Intl. to Bradley Intl., returning Tue, Sep 29, priced at CA $687 found 1 day ago
Wed, Sep 16 - Wed, Sep 23
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $702 Roundtrip, found 5 days ago
CA $702
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Sep 16 from Pearson Intl. to Bradley Intl., returning Wed, Sep 23, priced at CA $702 found 5 days ago
Fri, Oct 30 - Mon, Nov 2
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $708 Roundtrip, found 3 days ago
CA $708
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Oct 30 from Pearson Intl. to Bradley Intl., returning Mon, Nov 2, priced at CA $708 found 3 days ago
Sat, Sep 26 - Tue, Sep 29
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $711 Roundtrip, found 1 day ago
CA $711
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 26 from Pearson Intl. to Bradley Intl., returning Tue, Sep 29, priced at CA $711 found 1 day ago
Sat, Sep 26 - Tue, Sep 29
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $722 Roundtrip, found 1 day ago
CA $722
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Sep 26 from Pearson Intl. to Bradley Intl., returning Tue, Sep 29, priced at CA $722 found 1 day ago
Thu, Sep 24 - Tue, Sep 29
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $723 Roundtrip, found 6 days ago
CA $723
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Sep 24 from Pearson Intl. to Bradley Intl., returning Tue, Sep 29, priced at CA $723 found 6 days ago
Sat, Sep 26 - Tue, Sep 29
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $740 Roundtrip, found 1 day ago
CA $740
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 26 from Pearson Intl. to Bradley Intl., returning Tue, Sep 29, priced at CA $740 found 1 day ago
OriginDestinationTravel datesFlights from*
ORDEast HavenSeptember 25 to September 28CA $168
FLLEast HavenSeptember 18 to September 21CA $186
ATLEast HavenNovember 5 to November 11CA $188
MCOEast HavenSeptember 10 to September 14CA $189
TPAEast HavenOctober 2 to October 5CA $190
MCOWindsor LocksSeptember 11 to September 14CA $191
TPAWindsor LocksNovember 12 to November 15CA $224
FLLWindsor LocksOctober 2 to October 6CA $246
SJUEast HavenSeptember 16 to September 21CA $278
SJUWindsor LocksSeptember 16 to September 30CA $314
ORDWindsor LocksSeptember 10 to September 15CA $342
LAXWindsor LocksSeptember 16 to September 23CA $381
ATLWindsor LocksOctober 2 to October 4CA $393
CLTWindsor LocksSeptember 10 to September 14CA $656
DENWindsor LocksOctober 13 to October 18CA $924
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
TPAEast HavenAugust 30 to September 5CA $336
TPAWindsor LocksAugust 28 to August 31CA $361
MCOWindsor LocksAugust 28 to August 31CA $383
LAXWindsor LocksAugust 29 to September 5CA $474
SJUWindsor LocksAugust 28 to September 1CA $551
DENWindsor LocksAugust 28 to August 31CA $724
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Omni New Haven Hotel at Yale
4.0-star property

Omni New Haven Hotel at Yale

Sep 28 - Oct 1

3 night stay

Montreal (YUL) to New Haven (HVN)

Air Canada • Non-stop roundtrip • Coach
Price was CA $967, price is now CA $837 per person
CA $837
per person
found 1 hour ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Sep 3 - Sep 7

4 night stay

Calgary (YYC) to New Haven (HVN)

Delta • Non-stop roundtrip • Coach
Price was CA $4,452, price is now CA $2,718 per person
CA $2,718
per person
found 1 day ago
Head of Pond House
3.0-star property

Head of Pond House

Oct 4 - Oct 10

6 night stay

Toronto (YYZ) to New Haven (HVN)

Delta • Coach

New Haven (HVN) to Toronto (YYZ)

American Airlines • Coach
Price was CA $3,224, price is now CA $2,775 per person
CA $2,775
per person
found 23 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! (1,013 reviews)
"Clean room with crisp cold A/C. If you’re in the area and need a place to stay I would definitely recommend Pier Blue Inn. Helpful friendly staff."

Reviewed on Aug 22, 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! (289 reviews)
"Everything was great. I thought I read the breakfast was amazing, and instead it wasn't as good as Hampton Inn. Rooms were fine, but boring. Everything else was great. Perhaps I had gotten an overly high expectation from the posting."

Reviewed on Aug 22, 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 CA $168. 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 CA $168 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 $168 and CA $924. 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.