$51 Cheap flights to Middlesex County

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Top places to visit in Middlesex County

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

Old Saybrook

Cheap flights to Middlesex County from $51 One Way, $100 Round Trip

$100 return flights and $51 one-way flights to Middlesex County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Dec 4 - Fri, Dec 11
MCO
Orlando
BDL
Hartford
$100 Roundtrip, found 16 hours ago
$100
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Fri, Dec 4 from Orlando to Hartford, returning Fri, Dec 11, priced at $100 found 16 hours ago
Fri, Dec 4 - Sat, Dec 12
MCO
Orlando
BDL
Hartford
$102 Roundtrip, found 16 hours ago
$102
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Fri, Dec 4 from Orlando to Hartford, returning Sat, Dec 12, priced at $102 found 16 hours ago
Thu, Jan 21 - Sun, Jan 31
MCO
Orlando
HVN
New Haven
$106 Roundtrip, found 1 hour ago
$106
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Jan 21 from Orlando to New Haven, returning Sun, Jan 31, priced at $106 found 1 hour ago
Thu, Nov 5 - Sun, Nov 8
MCO
Orlando
BDL
Hartford
$109 Roundtrip, found 17 hours ago
$109
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, Nov 5 from Orlando to Hartford, returning Sun, Nov 8, priced at $109 found 17 hours ago
Thu, Jan 14 - Sun, Jan 17
MCO
Orlando
HVN
New Haven
$122 Roundtrip, found 8 hours ago
$122
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Thu, Jan 14 from Orlando to New Haven, returning Sun, Jan 17, priced at $122 found 8 hours ago
Thu, Oct 29 - Mon, Nov 2
MCO
Orlando
BDL
Hartford
$129 Roundtrip, found 1 day ago
$129
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Oct 29 from Orlando to Hartford, returning Mon, Nov 2, priced at $129 found 1 day ago
Fri, Jan 29 - Mon, Feb 1
TPA
Tampa
HVN
New Haven
$136 Roundtrip, found 2 hours ago
$136
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Fri, Jan 29 from Tampa to New Haven, returning Mon, Feb 1, priced at $136 found 2 hours ago
Fri, Dec 4 - Mon, Dec 7
TPA
Tampa
HVN
New Haven
$149 Roundtrip, found 1 day ago
$149
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Dec 4 from Tampa to New Haven, returning Mon, Dec 7, priced at $149 found 1 day ago
Thu, Jan 7 - Sun, Jan 10
TPA
Tampa
HVN
New Haven
$157 Roundtrip, found 22 hours ago
$157
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Thu, Jan 7 from Tampa to New Haven, returning Sun, Jan 10, priced at $157 found 22 hours ago
Fri, Jan 29 - Mon, Feb 1
TPA
Tampa
HVN
New Haven
$157 Roundtrip, found 2 hours ago
$157
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Fri, Jan 29 from Tampa to New Haven, returning Mon, Feb 1, priced at $157 found 2 hours ago
Fri, Jan 22 - Sun, Jan 31
TPA
Tampa
HVN
New Haven
$158 Roundtrip, found 20 hours ago
$158
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Fri, Jan 22 from Tampa to New Haven, returning Sun, Jan 31, priced at $158 found 20 hours ago
Sat, Oct 31 - Sat, Nov 7
TPA
Tampa
BDL
Hartford
$170 Roundtrip, found 2 days ago
$170
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Oct 31 from Tampa to Hartford, returning Sat, Nov 7, priced at $170 found 2 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
ATLEast HavenSeptember 19 to September 26$171
TPAEast HavenSeptember 19 to September 25$181
MCOEast HavenSeptember 19 to September 22$182
FLLEast HavenSeptember 19 to September 28$216
SJUEast HavenSeptember 19 to September 28$242
MCOWindsor LocksSeptember 19 to September 21$292
FLLWindsor LocksSeptember 19 to September 23$331
SJUWindsor LocksSeptember 18 to September 21$332
DCAWindsor LocksSeptember 18 to September 21$369
TPAWindsor LocksSeptember 18 to September 24$374
ORDWindsor LocksSeptember 19 to September 23$445
CLTWindsor LocksSeptember 18 to September 19$477
LAXWindsor LocksSeptember 19 to September 25$487
ATLWindsor LocksSeptember 19 to September 23$506
DENWindsor LocksSeptember 18 to September 20$993
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Middlesex County Accommodation Deals

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $104 total per night from Sep 22 to Sep 23
$104 total
Sep 22 - Sep 23
Total with taxes and fees
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. ...
8/10 Very Good! (1,009 reviews)
"Room need complete makeover"

Reviewed on Sep 15, 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
$218 nightly
The price is $251 total per night from Oct 7 to Oct 8
$251 total
Oct 7 - Oct 8
Total with taxes and fees
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 ...
8.8/10 Excellent! (1,002 reviews)
"Everything is perfect of what we need for short getaway to wind down labor day weekend. Short ride to New York . Thank you Waters edge resort and Spa . Westbrook Ct ."

Reviewed on Sep 12, 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
$179 nightly
The price is $206 total per night from Sep 16 to Sep 17
$206 total
Sep 16 - Sep 17
Total with taxes and fees
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 ...
9.4/10 Exceptional! (189 reviews)
"I went to post card cabins multiple times before Marriott takes over. I was very disappointed. The moment I entered I found used towels hanging! The sheets were so wrinkled I wasn’t sure if they changed it specially when I saw dirty towels. They left us s’mores but there was no stick. I called and ..."

Reviewed on Sep 15, 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
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $111 total per night from Sep 22 to Sep 23
$111 total
Sep 22 - Sep 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Mashantucket. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Foxwoods Resort Casino and ...
8.4/10 Very Good! (526 reviews)
"two trees is nice , nice grounds , pool, continental breakfast , have stayed before, will be back again."

Reviewed on Sep 15, 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.

Need a Car For After Your Flight?

Compact

Nissan Versa
  • 5 people
  • Unlimited mileage
Windsor Locks, Connecticut, USA
Nissan Versa

$27

$156 total
found 3 days ago
Compact Nissan Versa

Special

Vehicle determined upon pick-up Compact or Larger
  • 5 people
  • Unlimited mileage
Windsor Locks, Connecticut, USA
Vehicle determined upon pick-up Compact or Larger

$27

$157 total
found 3 days ago
Special Vehicle determined upon pick-up Compact or Larger

Economy

Mitsubishi Mirage
  • 4 people
  • Unlimited mileage
Windsor Locks, Connecticut, USA
Mitsubishi Mirage

$27

$156 total
found 3 days ago
Economy Mitsubishi Mirage

Midsize

Toyota Corolla
  • 5 people
  • Unlimited mileage
Windsor Locks, Connecticut, USA
Toyota Corolla

$27

$159 total
found 3 days ago
Midsize Toyota Corolla
Lowest prices found within the past 3 days. Prices and availability subject to change. Additional terms may apply.

Middlesex County

If you are looking for discount prices on flights to Middlesex County then look no further than Orbitz. With some of the best deals available, cutting-edge technology, and great customer service, Orbitz makes booking Middlesex County flights easy and affordable.

Booking Made Easy

With Orbitz’s Display Matrix, booking flights to Middlesex County is simple. Just one glance gives you all the pricing information you need, including your discounts and savings. View all your options before selecting and booking your perfect Middlesex County flights.

Manage Travel Plans on the Move

By using Orbitz’s free apps for iPhone and Android, and an easy-to-use mobile browser at m.orbitz.com, booking flights to Middlesex County has never been so convenient. Check for updates and alerts wherever you are, or manage your booking quickly. And we also offer mobile exclusive deals on hotels, so don’t delay—book right away.

The Complete Package

Orbitz makes it stress-free to book Middlesex County flights, and we can also help you figure out the rest of your trip just as easily. If you need great deals on hotels and car rentals following your flights to Middlesex County, just add the details to your booking and search for the cheapest deals out there. And why waste time lining up for admission to attractions and events? With Orbitz, you can book tickets in advance and waltz straight in.

Low Price Guarantee

Booking your Middlesex County flights with Orbitz guarantees low prices every day, all day—no matter when and where you book. You will always find the best deals available, coupled with extra great savings and discounts for all around great value.

Frequently asked questions

Which airlines fly to Middlesex County?
Search, compare and book flights from 24 airlines offering services to Middlesex County. So buckle up. Your flight to Bradley Intl. Airport (BDL) is ready for boarding with one of these leading carriers:

  • Air Canada - 17 flights to Middlesex County per month
  • JetBlue - 16 flights to Middlesex County per month

What is the best airport to fly to in Middlesex County?
Jet into Hartford, CT (HFD-Hartford - Brainard), the main gateway to Middlesex County. Organizing your flight to this region doesn't get much easier.
How much is a flight to Middlesex County?
The cost for a return flight to Middlesex County this week fluctuated between $100 and $993. If you were traveling one-way from Orlando (MCO), you could have snapped up prices from just $51.
How to book the cheapest flight to Middlesex County?
With some of the most amazing flight deals around, you'll always bag a bargain with Orbitz. The following suggestions will help you find cheap flights to Middlesex County — and leave you with more money to play with:

  • Consider taking off from or landing at other airports to save on your flight. Enter your preferred departure and arrival airports in the form fields, then choose the 'Nearby airports' function below. It will list your options, if any.
  • If your travel plans aren't set in stone, click on the 'Show flexible dates' option to view the flight deals for a range of departure dates. You may find an amazing fare.
  • To optimize your results, hit 'Show options.' You can search based on airlines, seating class, nonstop flights and refundable flights. You can also choose whether you want to fly in the morning, afternoon or evening under 'Sort & Filter' to the left.
  • The early bird catches the most rewarding savings, so book as soon as you know your travel dates. The cheapest fares get snapped up fast and prices generally rise as the departure date gets closer.
  • Think about bundling your flights, hotels and car rentals into a package with Orbitz to make your dollar go further.
  • Don't travel during peak seasons if possible. By steering clear of school vacations and summer, you can save plenty on your airfare.

What is the best time to book a flight to Middlesex County?
Book in January, February or August for the most competitive fares to Middlesex County. Once you've tracked down a bargain, lock it in — cheap flights tend to appear and vanish at the tap of a button.
What day of the week is the cheapest to book a flight to Middlesex County?
In general, Tuesdays, Wednesdays and Saturdays are the cheapest days to book flights to Middlesex County. If you're looking for the best airfares, search across those days and you just might land yourself a terrific flight deal.
What is the cheapest day of the week to fly to Middlesex County?
If you're after cheap flights to Middlesex County, depart at the start of the week. Orbitz data from 2020 shows Monday is the most affordable day to travel, followed by Tuesday. Saturday has the most expensive fares, so avoid this day and do your bank account a favor.
What is the cheapest month to fly to Middlesex County?
To secure cheap flights to Middlesex County, you should pack your bags and take off in August. Orbitz data has found that this is generally a great month to save on your ticket. If you're eager to fly to Middlesex County during June, bear in mind that this is the least affordable time of year to take a trip.
Which airlines allow free cancellation?
Plans change, and we think your ticket should be able to as well. That's why Orbitz makes it a cinch to search for flights with no change fees and free cancellation. Simply enter your departure and arrival destinations and then select "Filter by flexible change policies." How's that for peace of mind?
What do I need for the flight to Middlesex County?
From onboard activities to travel essentials like earplugs, there are a few things a seasoned flyer won't leave home without. To ensure you're organized for your journey, check out this handy list:

  • You'll need to take all relevant travel documents and identification. How much is dependent on where you're taking off from. When you book, you should always use the correct name, gender and birth date listed on your government-issued ID.
  • Stock your carry-on bag with activities and snacks and watch time whiz by on this medium-haul flight. Where possible, jump on the airport's Wi-Fi and download your favorite playlist or podcast to your phone prior to take off.
  • Plane cabins can often get quite cold. If you decide to travel during the peak of the Middlesex County summer, be sure to carry some extra layers of clothing to keep comfortable.

How do I get cheap first-class/business deals to Middlesex County?
If you think a business or first-class fare is out of your price range, think again. Here are some terrific tips to help you score a premium flight to Middlesex County for less:

  • Flexibility is important. By being open to a variety of travel dates, you'll have a better chance of picking up a deal on business or first-class airfares.
  • Find a low-cost carrier that has seats in business class. They often come with more legroom and a glass of Champagne — but without the premium price.
  • Bid for an upgrade in online auctions (if available) or upgrade your seat through your frequent flyer program.

What is the best time to go to Middlesex County?
If you'd like to soak up the unique vibe of Middlesex County in the tourist season, March, May and July are the prime months to visit. June 20 heralds the onset of the summer season in the Northern Hemisphere and is an awesome time to go if you relish the great outdoors. Around this time of the year, average daily temperatures range from 65 ºF to 80 ºF.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.