$52 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 $52 One Way, $102 Round Trip

$102 return flights and $52 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, Sep 2 - Sun, Sep 6
MCO
Orlando
HVN
New Haven
$102 Roundtrip, found 4 days ago
$102
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Sep 2 from Orlando to New Haven, returning Sun, Sep 6, priced at $102 found 4 days ago
Tue, Sep 1 - Wed, Sep 2
MCO
Orlando
HVN
New Haven
$112 Roundtrip, just found
$112
Roundtrip
just found
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando to New Haven, returning Wed, Sep 2, priced at $112 just found
Tue, Sep 1 - Tue, Sep 8
MCO
Orlando
HVN
New Haven
$117 Roundtrip, found 2 days ago
$117
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando to New Haven, returning Tue, Sep 8, priced at $117 found 2 days ago
Mon, Aug 31 - Mon, Aug 31
TPA
Tampa
HVN
New Haven
$118 Roundtrip, found 1 day ago
$118
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Mon, Aug 31 from Tampa to New Haven, returning Mon, Aug 31, priced at $118 found 1 day ago
Sat, Aug 29 - Mon, Aug 31
MCO
Orlando
BDL
Hartford
$121 Roundtrip, found 8 hours ago
$121
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Aug 29 from Orlando to Hartford, returning Mon, Aug 31, priced at $121 found 8 hours ago
Sat, Sep 19 - Mon, Sep 28
TPA
Tampa
BDL
Hartford
$142 Roundtrip, found 1 hour ago
$142
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Sep 19 from Tampa to Hartford, returning Mon, Sep 28, priced at $142 found 1 hour ago
Fri, Oct 23 - Mon, Oct 26
FLL
Fort Lauderdale
BDL
Hartford
$164 Roundtrip, found 2 days ago
$164
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Oct 23 from Fort Lauderdale to Hartford, returning Mon, Oct 26, priced at $164 found 2 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
FLLWindsor LocksJuly 4 to July 13$242
MCOEast HavenJuly 4 to July 11$242
ORDEast HavenJuly 3 to July 20$248
MCOWindsor LocksJuly 4 to July 10$255
SJUWindsor LocksJuly 4 to July 21$272
FLLEast HavenJuly 3 to July 9$303
TPAWindsor LocksJuly 3 to July 7$304
TPAEast HavenJuly 3 to July 17$324
ATLEast HavenJuly 5 to July 9$370
DCAWindsor LocksJuly 3 to July 5$412
SJUEast HavenJuly 4 to August 3$426
DENWindsor LocksJuly 5 to July 25$430
LAXWindsor LocksJuly 4 to July 8$466
CLTWindsor LocksJuly 3 to July 12$487
ATLWindsor LocksJuly 5 to July 8$620
*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
$340 nightly
The price is $391 total per night from Jul 21 to Jul 22
$391 total
Jul 21 - Jul 22
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! (1,000 reviews)
"we stayed for weekend had a great time beautiful room comfortable bed amazing spa tub restraunt food and bar convenient & delicious staff very nice"

Reviewed on Jun 25, 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 refundableReserve now, pay when you stay
$102 nightly
The price is $117 total per night from Jul 7 to Jul 8
$117 total
Jul 7 - Jul 8
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! (1,001 reviews)
"staff and parking"

Reviewed on Jun 22, 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
$184 nightly
The price is $212 total per night from Jul 30 to Jul 31
$212 total
Jul 30 - Jul 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 ...
9.6/10 Exceptional! (160 reviews)
"I stayed here, but there was no lantern or scissors provided, and the lantern in my friend’s unit was broken too. So I asked for a replacement, but I was told there wasn’t one available and to just deal with it. I asked them to help resolve the issue, but all they said was to talk to the manager ..."

Reviewed on Jun 26, 2026

Opens in a new windowPostcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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Best Western Mystic Hotel

Best Western Mystic Hotel

2.5 out of 5
48 Whitehall Ave Mystic CT
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $158 total per night from Jul 19 to Jul 20
$158 total
Jul 19 - Jul 20
Total with taxes and fees
Book a stay at this business-friendly hotel in Mystic. Enjoy free parking, an outdoor pool, and a fitness center. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (595 reviews)
"Yes very nice"

Reviewed on Jun 30, 2026

Opens in a new windowBest Western Mystic 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

Start your search for cheap flights to Middlesex County on Orbitz. Orbitz is where you will discover guaranteed low prices on Middlesex County flights, as well as all of the following conveniences:

Travel Updates on Your Mobile Device

Orbitz offers cutting-edge mobile tools for your smartphone. Whether you own an iPhone or an Android phone, you can benefit from Orbitz’s flight status updates and even book your future Middlesex County flights. You can also review and reserve hotel rooms for when your Middlesex County flights land and see other special offers.

Low Prices Guaranteed on Flights to Middlesex County

Orbitz offers large discounts on a wide range of Middlesex County flights. Through our easy-to-use site, you can find, plan, and reserve your desired flights to Middlesex County while taking advantage of the lowest fares around.

Customer Care When You Need It

Orbitz is dedicated to making your flight booking experience as stress-free as possible. If you need to cancel your reservation, you can do so at your own convenience by going to the Orbitz website. If you need to change your flights to Middlesex County to another time or date, you can contact our customer service representatives by phone, and they help you make the flight adjustments you need.

Loyalty Program Participation Opportunities

Orbitz lets you add your loyalty or frequent flyer account numbers when you book qualifying flights to Middlesex County. So don’t worry about missing out on earning miles or points simply because you aren’t booking with the airline directly. You can save on your flights, and rack up miles too.

Frequently asked questions

Which airlines fly to Middlesex County?
Search, compare and book flights from 14 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 $620. If you were traveling one-way from Orlando (MCO), you could have snapped up prices from just $52.
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.