Flights To Middlesex County - Cheap Flights Starting at CA $67

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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.

Mon, Sep 28 - Thu, Oct 1
ILM
Wilmington Intl.
HVN
Tweed - New Haven Regional
CA $115 Roundtrip, found 21 hours ago
CA $115
Roundtrip
found 21 hours ago
Select Avelo Airlines flight, departing Mon, Sep 28 from Wilmington Intl. to Tweed - New Haven Regional, returning Thu, Oct 1, priced at CA $115 found 21 hours ago
Thu, Oct 1 - Sun, Oct 4
ILM
Wilmington Intl.
HVN
Tweed - New Haven Regional
CA $128 Roundtrip, found 1 day ago
CA $128
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Thu, Oct 1 from Wilmington Intl. to Tweed - New Haven Regional, returning Sun, Oct 4, priced at CA $128 found 1 day ago
Thu, Oct 22 - Thu, Oct 29
ILM
Wilmington Intl.
BDL
Bradley Intl.
CA $141 Roundtrip, found 5 days ago
CA $141
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Oct 22 from Wilmington Intl. to Bradley Intl., returning Thu, Oct 29, priced at CA $141 found 5 days ago
Fri, Sep 25 - Mon, Sep 28
ORD
O'Hare Intl.
HVN
Tweed - New Haven Regional
CA $166 Roundtrip, found 18 hours ago
CA $166
Roundtrip
found 18 hours ago
Select Avelo Airlines flight, departing Fri, Sep 25 from O'Hare Intl. to Tweed - New Haven Regional, returning Mon, Sep 28, priced at CA $166 found 18 hours ago
Thu, Sep 10 - Mon, Sep 14
ORD
O'Hare Intl.
HVN
Tweed - New Haven Regional
CA $182 Roundtrip, found 4 days ago
CA $182
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Thu, Sep 10 from O'Hare Intl. to Tweed - New Haven Regional, returning Mon, Sep 14, priced at CA $182 found 4 days ago
Wed, Sep 16 - Wed, Sep 23
ORD
O'Hare Intl.
HVN
Tweed - New Haven Regional
CA $204 Roundtrip, found 4 days ago
CA $204
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Wed, Sep 16 from O'Hare Intl. to Tweed - New Haven Regional, returning Wed, Sep 23, priced at CA $204 found 4 days ago
Thu, Sep 17 - Mon, Sep 21
ORD
O'Hare Intl.
HVN
Tweed - New Haven Regional
CA $213 Roundtrip, found 22 hours ago
CA $213
Roundtrip
found 22 hours ago
Select Avelo Airlines flight, departing Thu, Sep 17 from O'Hare Intl. to Tweed - New Haven Regional, returning Mon, Sep 21, priced at CA $213 found 22 hours ago
Thu, Sep 10 - Sun, Sep 13
ORD
O'Hare Intl.
HVN
Tweed - New Haven Regional
CA $228 Roundtrip, found 2 days ago
CA $228
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Thu, Sep 10 from O'Hare Intl. to Tweed - New Haven Regional, returning Sun, Sep 13, priced at CA $228 found 2 days ago
Sat, Sep 26 - Tue, Sep 29
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $687 Roundtrip, found 2 days ago
CA $687
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 26 from Pearson Intl. to Bradley Intl., returning Tue, Sep 29, priced at CA $687 found 2 days ago
Sat, Sep 26 - Tue, Sep 29
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $687 Roundtrip, found 2 days ago
CA $687
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Sep 26 from Pearson Intl. to Bradley Intl., returning Tue, Sep 29, priced at CA $687 found 2 days ago
Wed, Oct 21 - Wed, Nov 18
YVR
Vancouver Intl.
BDL
Bradley Intl.
CA $732 Roundtrip, found 1 day ago
CA $732
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Oct 21 from Vancouver Intl. to Bradley Intl., returning Wed, Nov 18, priced at CA $732 found 1 day ago
OriginDestinationTravel datesFlights from*
ORDEast HavenSeptember 25 to September 28CA $166
FLLEast HavenSeptember 18 to September 21CA $186
ATLEast HavenNovember 5 to November 11CA $188
TPAEast HavenOctober 2 to October 5CA $190
MCOWindsor LocksSeptember 11 to September 14CA $200
MCOEast HavenSeptember 10 to September 14CA $202
TPAWindsor LocksOctober 29 to November 2CA $224
FLLWindsor LocksOctober 2 to October 6CA $246
ORDWindsor LocksSeptember 19 to October 17CA $358
SJUWindsor LocksSeptember 16 to September 30CA $361
LAXWindsor LocksSeptember 16 to September 23CA $389
ATLWindsor LocksOctober 2 to October 4CA $390
SJUEast HavenSeptember 7 to September 11CA $603
CLTWindsor LocksSeptember 10 to September 14CA $656
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
MCOWindsor LocksAugust 28 to August 31CA $388
TPAWindsor LocksAugust 28 to August 31CA $434
ORDWindsor LocksAugust 28 to September 13CA $531
LAXWindsor LocksAugust 29 to September 5CA $534
SJUWindsor LocksAugust 28 to September 1CA $605
DENWindsor LocksAugust 28 to August 31CA $788
*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 21 - Sep 24

3 night stay

Montreal (YUL) to New Haven (HVN)

Delta • Roundtrip • Coach
Price was CA $981, price is now CA $839 per person
CA $839
per person
found 24 hours ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Oct 15 - Oct 19

4 night stay

Toronto (YYZ) to New Haven (HVN)

Air Canada • Roundtrip • Coach
Price was CA $4,142, price is now CA $1,855 per person
CA $1,855
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 1 day 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! (1,015 reviews)
"Absolute gem really cool giant picnic table in the middle of the room, which is great for kids are just getting work done. The staff is absolutely wonderful. The view is gorgeous. If you stay on the backside of the hotel cannot recommend this place enough. What a surprise incredible bargain."

Reviewed on Aug 23, 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.
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! (293 reviews)
"Excellent alternative to the main Foxwoods hotel."

Reviewed on Aug 23, 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 $115. 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, 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 $115 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 $115 and CA $788. 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.