$51 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

rocks at low tide on beach at Harkness State Park
FlightsFlights
FlightsFlights

Old Saybrook

Old Saybrook

Cheap flights to Middlesex County from $51 One Way, $102 Round Trip

$102 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.

Thu, Sep 3 - Tue, Sep 8
MCO
Orlando
HVN
New Haven
$102 Roundtrip, found 6 days ago
$102
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando to New Haven, returning Tue, Sep 8, priced at $102 found 6 days ago
Sat, Sep 5 - Tue, Sep 8
MCO
Orlando
HVN
New Haven
$112 Roundtrip, found 6 days ago
$112
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sat, Sep 5 from Orlando to New Haven, returning Tue, Sep 8, priced at $112 found 6 days ago
Tue, Sep 1 - Sun, Sep 6
MCO
Orlando
HVN
New Haven
$118 Roundtrip, found 5 days ago
$118
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando to New Haven, returning Sun, Sep 6, priced at $118 found 5 days ago
Thu, Sep 3 - Sun, Sep 6
MCO
Orlando
HVN
New Haven
$120 Roundtrip, found 1 day ago
$120
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando to New Haven, returning Sun, Sep 6, priced at $120 found 1 day ago
Tue, Sep 1 - Sun, Sep 6
MCO
Orlando
HVN
New Haven
$130 Roundtrip, found 5 days ago
$130
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando to New Haven, returning Sun, Sep 6, priced at $130 found 5 days ago
Thu, Aug 27 - Sun, Aug 30
CVG
Cincinnati
BDL
Hartford
$132 Roundtrip, found 4 hours ago
$132
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Thu, Aug 27 from Cincinnati to Hartford, returning Sun, Aug 30, priced at $132 found 4 hours ago
Wed, Sep 2 - Sat, Sep 5
MCO
Orlando
BDL
Hartford
$134 Roundtrip, found 2 days ago
$134
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Sep 2 from Orlando to Hartford, returning Sat, Sep 5, priced at $134 found 2 days ago
Tue, Aug 25 - Sun, Aug 30
CVG
Cincinnati
BDL
Hartford
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Aug 25 from Cincinnati to Hartford, returning Sun, Aug 30, priced at $137 found 1 day ago
Tue, Aug 25 - Sun, Aug 30
CVG
Cincinnati
BDL
Hartford
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Aug 25 from Cincinnati to Hartford, returning Sun, Aug 30, priced at $142 found 1 day ago
Sun, Aug 16 - Tue, Aug 18
CVG
Cincinnati
BDL
Hartford
$147 Roundtrip, found 6 days ago
$147
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sun, Aug 16 from Cincinnati to Hartford, returning Tue, Aug 18, priced at $147 found 6 days ago
Wed, Aug 26 - Tue, Sep 1
LAX
Los Angeles
BDL
Hartford
$239 Roundtrip, found 5 days ago
$239
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Aug 26 from Los Angeles to Hartford, returning Tue, Sep 1, priced at $239 found 5 days ago
Thu, Aug 6 - Sun, Aug 9
CVG
Cincinnati
BDL
Hartford
$254 Roundtrip, found 3 hours ago
$254
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Aug 6 from Cincinnati to Hartford, returning Sun, Aug 9, priced at $254 found 3 hours ago
Loading

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
MCOEast HavenJune 20 to July 1$215
TPAEast HavenJune 20 to July 5$232
MCOWindsor LocksJune 20 to June 22$274
ORDWindsor LocksJune 20 to September 29$331
TPAWindsor LocksJune 20 to June 24$331
FLLEast HavenJune 19 to June 26$333
ATLEast HavenJune 19 to June 28$347
FLLWindsor LocksJune 20 to June 22$366
CLTWindsor LocksJune 20 to June 23$373
ATLWindsor LocksJune 20 to June 22$380
DCAWindsor LocksJune 19 to June 21$383
SJUWindsor LocksJune 21 to August 21$399
DENWindsor LocksJune 21 to June 26$450
LAXWindsor LocksJune 20 to June 24$589
SJUEast HavenJune 20 to June 22$773
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Middlesex County Accommodation Deals

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
The price is $361 total per night from Jun 17 to Jun 18
$361 total
per night
Jun 17 - Jun 18
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)
"The resort was very nice and well maintained. I would say the staff wasn't that great. I've much better experiences. I enjoyed my massage and spa. The only complaint I have is that at a room near mine room was very loud and woke me up at 11:30. I couldn't get a response from dialing 0 and I tried ..."

Reviewed on Jun 14, 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
Fully refundable
The price is $126 total per night from Jun 18 to Jun 19
$126 total
per night
Jun 18 - Jun 19
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! (1,006 reviews)
"very nice stay"

Reviewed on Jun 15, 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
The price is $212 total per night from Jul 16 to Jul 17
$212 total
per night
Jul 16 - Jul 17
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 ...
9.6/10 Exceptional! (156 reviews)
"Def not up to the Marriott Bonvoy brand. These aren’t cabins - they’re tiny homes/mobile homes. They are super small. Mine didn’t have AC and it was a hot muggy weekend. In town for a funeral and the room has no hair dryer, no mirror - at all nevermind a full length, no closet and no bathroom sink, ..."

Reviewed on Jun 8, 2026

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
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is $127 total per night from Jun 29 to Jun 30
$127 total
per night
Jun 29 - Jun 30
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 ...
9.2/10 Wonderful! (2,197 reviews)
"Always feel back home when I see the smiles of the front desk staffs. Great location, convenient to everything! Clean rooms with decent space for travelers like me."

Reviewed on Jun 16, 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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Middlesex County

Snag some “suite” deals when you add cheap hotel rooms to Middlesex County flights at Orbitz. You can score tickets to ballgames, concerts and other activities while planning your low fare flights. For non-stop air tickets or planned layovers, Orbitz is your discount travel resource.

Budget Prices, Luxury Life

Find mobile-only bargains on your home away from home with Orbitz cutting-edge mobile tools. Search domestic and international hotels at Orbitz On the Go. Find free travel planning apps for your iPhone, Android or iPad. You’ll always get our guaranteed low prices on your favorite hotels and flights to Middlesex County.

Fun for All

While shopping Orbitz sales on Middlesex County flights, remember to throw in some fun. Ticket sales for music, theatre, sports and more can be found on the Activities page. Just tell us what you want to do, and Orbitz will save your seat.

Non-Stop or Stop and Visit

Will you be flying round-trip or one-way? Going directly from Point A to Point B? Maybe you’d like to have dinner with family and friends along the way. Whether you need non-stop flights to {destination.name} or lowest cost layovers on Middlesex County flights, you will always find the best air travel prices at Orbitz.

All in One

Now you can custom design the perfect travel package with Orbitz and save more when booking your flights to Middlesex County. Do you have a favorite airline, hotel or car rental company? Every page at Orbitz gives you complete freedom to create your travel plans according to your unique wants and needs. Orbitz is designed to meet your discount travel planning needs completely and conveniently.

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 $102 and $773. 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.