Flights To Middlesex County - Cheap Flights Starting at CA $72

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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, Jun 4 - Sun, Jun 7
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
CA $174 Roundtrip, found 5 days ago
CA $174
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jun 4 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Jun 7, priced at CA $174 found 5 days ago
Thu, Jun 4 - Sun, Jun 7
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
CA $181 Roundtrip, found 5 days ago
CA $181
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jun 4 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Jun 7, priced at CA $181 found 5 days ago
Thu, May 28 - Fri, May 29
ORF
Norfolk Intl.
BDL
Bradley Intl.
CA $183 Roundtrip, found 2 days ago
CA $183
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, May 28 from Norfolk Intl. to Bradley Intl., returning Fri, May 29, priced at CA $183 found 2 days ago
Thu, Jun 4 - Sun, Jun 7
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
CA $188 Roundtrip, found 5 days ago
CA $188
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jun 4 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, Jun 7, priced at CA $188 found 5 days ago
Thu, May 28 - Sun, May 31
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
CA $244 Roundtrip, found 1 day ago
CA $244
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, May 28 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 31, priced at CA $244 found 1 day ago
Thu, May 28 - Sun, May 31
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
CA $259 Roundtrip, found 1 day ago
CA $259
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, May 28 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 31, priced at CA $259 found 1 day ago
Thu, May 28 - Sun, May 31
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
CA $266 Roundtrip, found 11 hours ago
CA $266
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Thu, May 28 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 31, priced at CA $266 found 11 hours ago
Thu, May 28 - Sun, May 31
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
CA $274 Roundtrip, found 1 hour ago
CA $274
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, May 28 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 31, priced at CA $274 found 1 hour ago
Wed, Aug 12 - Wed, Aug 19
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $711 Roundtrip, found 10 hours ago
CA $711
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Wed, Aug 12 from Pearson Intl. to Bradley Intl., returning Wed, Aug 19, priced at CA $711 found 10 hours ago
Wed, Jun 24 - Tue, Jun 30
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $777 Roundtrip, found 4 days ago
CA $777
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jun 24 from Pearson Intl. to Bradley Intl., returning Tue, Jun 30, priced at CA $777 found 4 days ago
Mon, Jul 20 - Wed, Jul 29
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $867 Roundtrip, found 8 hours ago
CA $867
Roundtrip
found 8 hours ago
Select WestJet flight, departing Mon, Jul 20 from Pearson Intl. to Bradley Intl., returning Wed, Jul 29, priced at CA $867 found 8 hours ago
OriginDestinationTravel datesFlights from*
TPAEast HavenAugust 27 to August 31CA $164
ORDEast HavenJune 12 to June 14CA $168
MCOEast HavenJune 18 to July 5CA $178
TPAWindsor LocksAugust 27 to September 6CA $206
MCOWindsor LocksJune 6 to June 10CA $212
ATLEast HavenJune 25 to June 29CA $310
FLLEast HavenJune 13 to June 18CA $345
DCAWindsor LocksJuly 9 to July 16CA $350
LAXWindsor LocksAugust 27 to August 30CA $373
FLLWindsor LocksJune 17 to June 22CA $395
ORDWindsor LocksJuly 24 to July 27CA $510
DENWindsor LocksAugust 25 to August 31CA $515
SJUWindsor LocksJune 19 to June 24CA $723
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
TPAEast HavenMay 29 to May 31CA $370
TPAWindsor LocksMay 31 to June 4CA $384
LAXWindsor LocksMay 29 to June 9CA $441
*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

Aug 10 - Aug 15

5 night stay

Detroit (DTW) to New Haven (HVN)

Delta • Roundtrip • Coach
Price was CA $955, price is now CA $694 per person
CA $694
per person
found 14 hours ago
Three Ducks
2.0-star property

Three Ducks

Aug 10 - Aug 15

5 night stay

Detroit (DTW) to Westhampton (FOK)

Delta • Roundtrip • Coach
Price was CA $3,876, price is now CA $2,658 per person
CA $2,658
per person
found 14 hours ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Jun 5 - Jun 9

4 night stay

Toronto (YYZ) to New Haven (HVN)

Air Canada • Roundtrip • Coach
Price was CA $3,636, price is now CA $2,648 per person
CA $2,648
per person
found 11 hours 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! (1,001 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! (1,002 reviews)
"Comfortable for a nights stay. Close to nice restaurants and shopping."

Reviewed on May 21, 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! (152 reviews)
"The most peaceful mothers day weekend ever"

Reviewed on May 16, 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 Louis' Lunch are located nearby.
9.2/10 Wonderful! (2,135 reviews)
"The complimentary coffee was much appreciated. The staff were so great and helpful, and genuinely want your stay to be as perfect as possible. One thing that was repeatedly bothersome, even at 7:00 a.m., was the overly loud music in the back of the lobby area, and it was not calming music, it was ..."

Reviewed on May 22, 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 $164. 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, June 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 $164 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 $164 and CA $867. 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.