Flights To Middlesex County - Cheap Flights Starting at CA $261

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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.

Tue, Dec 22 - Tue, Dec 29
DEN
Denver Intl.
BDL
Bradley Intl.
CA $531 Roundtrip, found 5 days ago
CA $531
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Dec 22 from Denver Intl. to Bradley Intl., returning Tue, Dec 29, priced at CA $531 found 5 days ago
Tue, Dec 22 - Wed, Dec 30
DEN
Denver Intl.
BDL
Bradley Intl.
CA $533 Roundtrip, found 2 days ago
CA $533
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Dec 22 from Denver Intl. to Bradley Intl., returning Wed, Dec 30, priced at CA $533 found 2 days ago
Tue, Dec 22 - Tue, Dec 29
DEN
Denver Intl.
BDL
Bradley Intl.
CA $559 Roundtrip, found 5 days ago
CA $559
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Dec 22 from Denver Intl. to Bradley Intl., returning Tue, Dec 29, priced at CA $559 found 5 days ago
Tue, Dec 22 - Tue, Dec 29
DEN
Denver Intl.
BDL
Bradley Intl.
CA $598 Roundtrip, found 21 hours ago
CA $598
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Tue, Dec 22 from Denver Intl. to Bradley Intl., returning Tue, Dec 29, priced at CA $598 found 21 hours ago
Mon, Nov 9 - Sat, Nov 14
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $688 Roundtrip, found 9 hours ago
CA $688
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Mon, Nov 9 from Pearson Intl. to Bradley Intl., returning Sat, Nov 14, priced at CA $688 found 9 hours ago
Mon, Nov 9 - Sat, Nov 14
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $688 Roundtrip, found 9 hours ago
CA $688
Roundtrip
found 9 hours ago
Select Delta flight, departing Mon, Nov 9 from Pearson Intl. to Bradley Intl., returning Sat, Nov 14, priced at CA $688 found 9 hours ago
Tue, Oct 20 - Tue, Oct 27
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $703 Roundtrip, found 3 days ago
CA $703
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Oct 20 from Pearson Intl. to Bradley Intl., returning Tue, Oct 27, priced at CA $703 found 3 days ago
Tue, Oct 20 - Tue, Oct 27
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $703 Roundtrip, found 3 days ago
CA $703
Roundtrip
found 3 days ago
Select United flight, departing Tue, Oct 20 from Pearson Intl. to Bradley Intl., returning Tue, Oct 27, priced at CA $703 found 3 days ago
OriginDestinationTravel datesFlights from*
MCOWindsor LocksOctober 24 to October 29CA $240
TPAWindsor LocksDecember 4 to December 13CA $245
FLLEast HavenNovember 13 to November 15CA $266
FLLWindsor LocksNovember 12 to November 16CA $277
SJUEast HavenNovember 20 to November 28CA $307
ATLEast HavenDecember 7 to December 10CA $325
ORDEast HavenOctober 30 to November 1CA $330
TPAEast HavenOctober 30 to November 1CA $353
SJUWindsor LocksNovember 6 to November 13CA $361
MCOEast HavenOctober 28 to November 1CA $418
LAXWindsor LocksOctober 24 to October 30CA $471
DENWindsor LocksDecember 22 to December 29CA $531
ATLWindsor LocksOctober 23 to October 25CA $732
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
MCOWindsor LocksOctober 10 to October 18CA $502
SJUWindsor LocksOctober 9 to October 19CA $512
TPAWindsor LocksOctober 11 to October 15CA $604
FLLWindsor LocksOctober 10 to October 12CA $673
MCOEast HavenOctober 10 to October 18CA $738
LAXWindsor LocksOctober 10 to October 12CA $799
DENWindsor LocksOctober 9 to October 12CA $1,154
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Mayflower Motel Milford
2.0-star property

Mayflower Motel Milford

Oct 15 - Oct 18

3 night stay

Detroit (DTT) to New Haven (HVN)

Xtra Airways • Roundtrip • Coach
Price was CA $592, price is now CA $536 per person
CA $536
per person
found 7 hours ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Oct 9 - Oct 11

2 night stay

Toronto (YTO) to New Haven (HVN)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $2,518, price is now CA $1,535 per person
CA $1,535
per person
found 1 day ago
Clarion Inn North Haven - New Haven North
3.0-star property

Clarion Inn North Haven - New Haven North

Oct 15 - Oct 18

3 night stay

Detroit (DTT) to New Haven (HVN)

Xtra Airways • Roundtrip • Coach
Price was CA $657, price is now CA $611 per person
CA $611
per person
found 7 hours 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! (1,006 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.
8.8/10 Excellent! (1,001 reviews)
"Scenery was picture postcard perfect! Highly recommend balcony view from the main hotel Room service was excellent and the dining room staff and food were wonderful Only downside. There were no robes in the room and if you drank the bottled water, you were charged. Not really disclosed very well ..."

Reviewed on Oct 5, 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 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! (753 reviews)
"I will definitely book again. Everything about my stay was great! I was very pleased with the overall cleanliness as well."

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 CA $240. 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 16 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, December 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 $240 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 $240 and CA $1,154. 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.