$62 Cheap flights to Middlesex County

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Top places to visit in Middlesex County

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

Old Saybrook

Old Saybrook

Cheap flights to Middlesex County from $62 One Way, $128 Round Trip

$128 return flights and $62 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.

Sat, Dec 5 - Sat, Dec 12
MCO
Orlando
HVN
New Haven
$128 Roundtrip, found 9 hours ago
$128
Roundtrip
found 9 hours ago
Select Avelo Airlines flight, departing Sat, Dec 5 from Orlando to New Haven, returning Sat, Dec 12, priced at $128 found 9 hours ago
Fri, Jan 8 - Mon, Jan 11
TPA
Tampa
HVN
New Haven
$130 Roundtrip, found 3 hours ago
$130
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Fri, Jan 8 from Tampa to New Haven, returning Mon, Jan 11, priced at $130 found 3 hours ago
Wed, Nov 18 - Sat, Dec 5
MCO
Orlando
HVN
New Haven
$134 Roundtrip, found 3 days ago
$134
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Wed, Nov 18 from Orlando to New Haven, returning Sat, Dec 5, priced at $134 found 3 days ago
Fri, Jan 8 - Mon, Jan 11
TPA
Tampa
HVN
New Haven
$139 Roundtrip, found 3 hours ago
$139
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Fri, Jan 8 from Tampa to New Haven, returning Mon, Jan 11, priced at $139 found 3 hours ago
Thu, Dec 3 - Mon, Dec 7
MCO
Orlando
BDL
Hartford
$149 Roundtrip, found 1 day ago
$149
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Dec 3 from Orlando to Hartford, returning Mon, Dec 7, priced at $149 found 1 day ago
Fri, Jan 22 - Sun, Feb 7
TPA
Tampa
BDL
Hartford
$163 Roundtrip, found 2 days ago
$163
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jan 22 from Tampa to Hartford, returning Sun, Feb 7, priced at $163 found 2 days ago
Loading

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
MCOEast HavenNovember 7 to November 10$162
SJUEast HavenNovember 6 to November 14$169
ATLEast HavenNovember 7 to November 11$178
FLLEast HavenNovember 6 to November 9$196
MCOWindsor LocksNovember 7 to November 14$203
TPAWindsor LocksNovember 7 to November 14$225
TPAEast HavenNovember 6 to November 8$247
FLLWindsor LocksNovember 7 to November 11$268
SJUWindsor LocksNovember 6 to November 8$289
LAXWindsor LocksNovember 7 to November 10$378
ORDWindsor LocksNovember 6 to November 9$415
DCAWindsor LocksNovember 6 to November 7$418
ATLWindsor LocksNovember 8 to November 10$451
DENWindsor LocksNovember 8 to November 12$455
CLTWindsor LocksNovember 6 to November 8$946
*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 refundable
$76 nightly
The price is $88 total per night from Nov 1 to Nov 2
$88 total
Nov 1 - Nov 2
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! (1,004 reviews)
"I'm not sure how this hotel has good ratings. It is run down and in disrepair. My door would not even open per the front desk clerk so she walked me to my room where the door was open slightly and said here's your key but you can't really use it because the door is so stiff it won't open from the ..."

Reviewed on Oct 30, 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
Fully refundableReserve now, pay when you stay
$200 nightly
The price is $230 total per night from Nov 29 to Nov 30
$230 total
Nov 29 - Nov 30
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 ...
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
$167 nightly
The price is $192 total per night from Nov 30 to Dec 1
$192 total
Nov 30 - Dec 1
Total with taxes and fees
Stay at this cabin in East Haddam. Enjoy free parking and patios. Popular attractions Machimoodus State Park and Amasa Day House are located nearby.
Opens in a new windowPostcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Two Trees Inn

Two Trees Inn

2.5 out of 5
240 Indiantown Rd Mashantucket CT
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $120 total per night from Nov 8 to Nov 9
$120 total
Nov 8 - Nov 9
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 ...
8.6/10 Excellent! (981 reviews)
"It was awesome ty"

Reviewed on Oct 30, 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

$21

$130 total
found 1 day ago
Compact Nissan Versa

Standard Pickup Regular Cab

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

$22

$133 total
found 1 day ago
Standard Pickup Regular Cab Toyota Tacoma

Midsize

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

$22

$134 total
found 1 day ago
Midsize Toyota Corolla

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

$23

$140 total
found 1 day ago
Special Vehicle determined upon pick-up Compact or Larger

Middlesex County

End your search for discount fares on flights to Middlesex County. Orbitz has all the best prices on Middlesex County flights. With Orbitz, you can expect:

Cheap Deals on Flights to Middlesex County

We offer big discounts and last-minute savings on Middlesex County flights. We make it easy for you to research, plan, and book your flight to Middlesex County — all while offering great low fares. With guaranteed low prices and cutting-edge mobile tools, the perfect trip begins on Orbitz.

Travel Convenience on the Go

Get alerts, updates, or book your Middlesex County flight or other flights wherever you are. Download our free apps for iPhone, Android, and iPad or visit our mobile site at m.orbitz.com to conveniently review or change your air travel plans. We can also send free alerts about your Middlesex County flight to your email or mobile phone, so you get advance warning about potential disruptions and flight delays. Need to book a hotel with your Middlesex County flight? Access exclusive, mobile-only deals via our mobile site and free apps – even on the same day.

Great Customer Care

We want to make your travel booking experience smooth and easy, from planning and researching Middlesex County flights to the actual booking. If you want to cancel your flight to Middlesex County, many tickets can be conveniently cancelled online. Contact our Customer Service to make changes to your air ticket.

Miles or Points Toward Frequent Flyer Programs

Much like booking with an airline directly, you can earn frequent flyer miles or points on qualified flights to Middlesex County with Orbitz. When completing your booking, just fill in your frequent flyer number for the airline you are flying with or for one of its available partner airlines.

Frequently asked questions

Which airlines fly to Middlesex County?
Search, compare and book flights from 12 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 $128 and $946. If you were traveling one-way from Tampa (TPA), you could have snapped up prices from just $62.
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.