$48 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 $48 One Way, $98 Round Trip

$98 return flights and $48 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.

Wed, Aug 26 - Thu, Aug 27
MCO
Orlando
HVN
New Haven
$98 Roundtrip, just found
$98
Roundtrip
just found
Select Avelo Airlines flight, departing Wed, Aug 26 from Orlando to New Haven, returning Thu, Aug 27, priced at $98 just found
Tue, Sep 1 - Tue, Sep 1
MCO
Orlando
HVN
New Haven
$111 Roundtrip, found 4 hours ago
$111
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando to New Haven, returning Tue, Sep 1, priced at $111 found 4 hours ago
Wed, Sep 2 - Sun, Sep 6
MCO
Orlando
HVN
New Haven
$112 Roundtrip, found 3 hours ago
$112
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Wed, Sep 2 from Orlando to New Haven, returning Sun, Sep 6, priced at $112 found 3 hours ago
Wed, Oct 14 - Wed, Oct 21
ORD
Chicago
HVN
New Haven
$118 Roundtrip, just found
$118
Roundtrip
just found
Select Avelo Airlines flight, departing Wed, Oct 14 from Chicago to New Haven, returning Wed, Oct 21, priced at $118 just found
Wed, Sep 9 - Sun, Sep 13
ORD
Chicago
HVN
New Haven
$119 Roundtrip, just found
$119
Roundtrip
just found
Select Avelo Airlines flight, departing Wed, Sep 9 from Chicago to New Haven, returning Sun, Sep 13, priced at $119 just found
Mon, Aug 31 - Tue, Sep 1
MCO
Orlando
BDL
Hartford
$128 Roundtrip, found 1 day ago
$128
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Aug 31 from Orlando to Hartford, returning Tue, Sep 1, priced at $128 found 1 day ago
Fri, Aug 21 - Mon, Aug 24
ORD
Chicago
HVN
New Haven
$130 Roundtrip, just found
$130
Roundtrip
just found
Select Avelo Airlines flight, departing Fri, Aug 21 from Chicago to New Haven, returning Mon, Aug 24, priced at $130 just found
Thu, Aug 27 - Fri, Aug 28
ORD
Chicago
HVN
New Haven
$132 Roundtrip, found 1 hour ago
$132
Roundtrip
found 1 hour ago
Select Avelo Airlines flight, departing Thu, Aug 27 from Chicago to New Haven, returning Fri, Aug 28, priced at $132 found 1 hour ago
Fri, Sep 11 - Sun, Sep 20
MCO
Orlando
BDL
Hartford
$135 Roundtrip, found 3 hours ago
$135
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, Sep 11 from Orlando to Hartford, returning Sun, Sep 20, priced at $135 found 3 hours ago
Fri, Aug 14 - Mon, Aug 24
ORD
Chicago
HVN
New Haven
$136 Roundtrip, found 1 day ago
$136
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Fri, Aug 14 from Chicago to New Haven, returning Mon, Aug 24, priced at $136 found 1 day ago
Thu, Aug 20 - Mon, Aug 24
ORD
Chicago
HVN
New Haven
$140 Roundtrip, found 4 hours ago
$140
Roundtrip
found 4 hours ago
Select Avelo Airlines flight, departing Thu, Aug 20 from Chicago to New Haven, returning Mon, Aug 24, priced at $140 found 4 hours ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
ATLEast HavenAugust 7 to August 8$171
FLLEast HavenAugust 8 to August 22$174
TPAEast HavenAugust 8 to August 24$230
SJUWindsor LocksAugust 8 to August 26$263
TPAWindsor LocksAugust 8 to August 18$267
MCOWindsor LocksAugust 7 to August 13$283
MCOEast HavenAugust 8 to August 12$295
CLTWindsor LocksAugust 8 to August 15$325
ATLWindsor LocksAugust 8 to September 13$328
ORDWindsor LocksAugust 8 to August 12$351
DCAWindsor LocksAugust 7 to August 9$353
FLLWindsor LocksAugust 8 to August 16$359
LAXWindsor LocksAugust 8 to August 22$385
DENWindsor LocksAugust 8 to August 15$417
SJUEast HavenAugust 7 to August 10$523
*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
$104 nightly
The price is $120 total per night from Aug 4 to Aug 5
$120 total
Aug 4 - Aug 5
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! (1,005 reviews)
"The room was nice and very well renovated, HOWEVER the floor was so dirty that it left out socks black after walking around the room. The bed was clean and the location was good but the cleanliness of the room in general left something to be desired."

Reviewed on Jul 31, 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
$264 nightly
The price is $304 total per night from Aug 31 to Sep 1
$304 total
Aug 31 - Sep 1
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! (1,010 reviews)
"Nothing"

Reviewed on Jul 31, 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
$224 nightly
The price is $258 total per night from Aug 30 to Aug 31
$258 total
Aug 30 - Aug 31
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! (173 reviews)
"It was clean and private with cute surprises around. The s'mores box for two and camping wood already to go into the pit such a nice touch."

Reviewed on Jul 26, 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
$134 nightly
The price is $154 total per night from Aug 13 to Aug 14
$154 total
Aug 13 - Aug 14
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! (135 reviews)
"Food was not good bartender was friendly"

Reviewed on Jul 31, 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?

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

Finding cheap flights to Middlesex County is easy when you have Orbitz at your fingertips. Not only does Orbitz offer great deals on Middlesex County flights, but we also include some special extras to make booking a breeze. Just check out our:

Mobile Site and Apps

With Orbitz’s mobile site, m.orbitz.com, you can book your flights to Middlesex County through your smartphone or tablet’s Web browser. Plus, our free downloadable apps for Android and iPhone mean it’s just a simple click to access your flight updates and alerts. You can even book exclusive mobile-only deals on hotels to go with your flights to Middlesex County—even on the same day.

Pick and Choose or Book Full Vacation Packages

Don’t just be satisfied with great deals on Middlesex County flights—go for the full package! With Orbitz, you can also find fantastic savings on the perfect hotel, car rental, cruise, and even activities, so you don’t waste your trip waiting in line but have the time to enjoy your trip. Pick and choose the add-ons you need, or book an entire vacation package for greater overall discounts.

Rewards That Are Miles Better

Booking directly with an airline earns you air miles or points, and you can get those same rewards with booking on Orbitz too. When you book qualifying flights to Middlesex County with Orbitz, just add in your frequent flyer number during your online booking and your details will be sent to your program.

Great Deals Every Day

Add in our extra savings on packages, free nights, and other discounts, and you know you are in good hands.

Frequently asked questions

Which airlines fly to Middlesex County?
Search, compare and book flights from 22 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 $98 and $523. If you were traveling one-way from Orlando (MCO), you could have snapped up prices from just $48.
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.