$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, found 16 hours ago
$98
Roundtrip
found 16 hours ago
Select Avelo Airlines flight, departing Wed, Aug 26 from Orlando to New Haven, returning Thu, Aug 27, priced at $98 found 16 hours ago
Wed, Sep 2 - Sat, Sep 5
MCO
Orlando
HVN
New Haven
$101 Roundtrip, found 9 hours ago
$101
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Sep 2 from Orlando to New Haven, returning Sat, Sep 5, priced at $101 found 9 hours ago
Wed, Sep 2 - Sat, Sep 5
MCO
Orlando
HVN
New Haven
$106 Roundtrip, found 9 hours ago
$106
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Sep 2 from Orlando to New Haven, returning Sat, Sep 5, priced at $106 found 9 hours ago
Wed, Sep 2 - Sat, Sep 5
MCO
Orlando
HVN
New Haven
$111 Roundtrip, found 9 hours ago
$111
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Sep 2 from Orlando to New Haven, returning Sat, Sep 5, priced at $111 found 9 hours ago
Wed, Oct 7 - Wed, Oct 14
MCO
Orlando
HVN
New Haven
$114 Roundtrip, found 9 hours ago
$114
Roundtrip
found 9 hours ago
Select Avelo Airlines flight, departing Wed, Oct 7 from Orlando to New Haven, returning Wed, Oct 14, priced at $114 found 9 hours ago
Fri, Sep 11 - Sun, Sep 20
MCO
Orlando
BDL
Hartford
$135 Roundtrip, just found
$135
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Sep 11 from Orlando to Hartford, returning Sun, Sep 20, priced at $135 just found

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
ORDEast HavenAugust 7 to August 17$165
ATLEast HavenAugust 7 to August 8$171
TPAEast HavenAugust 8 to August 24$230
MCOEast HavenAugust 9 to August 12$272
FLLEast HavenAugust 7 to August 12$298
FLLWindsor LocksAugust 8 to August 12$315
SJUWindsor LocksAugust 9 to August 31$322
TPAWindsor LocksAugust 8 to August 9$324
MCOWindsor LocksAugust 9 to August 12$335
ATLWindsor LocksAugust 8 to August 9$355
DCAWindsor LocksAugust 8 to August 9$391
DENWindsor LocksAugust 8 to August 17$416
CLTWindsor LocksAugust 8 to August 9$436
SJUEast HavenAugust 8 to August 14$557
LAXWindsor LocksAugust 7 to August 15$603
*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 25 to Aug 26
$120 total
Aug 25 - Aug 26
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. ...
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
$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! (1,004 reviews)
"Very clean room, some hidden costs added during check in. Resort fee tax and town or state"

Reviewed on Aug 3, 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
$215 nightly
The price is $247 total per night from Sep 2 to Sep 3
$247 total
Sep 2 - Sep 3
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 ...
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 Aug 16 to Aug 17
$158 total
Aug 16 - Aug 17
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! (661 reviews)
"The rooms my family stayed in both smelled and clearly had mold issues. The staff were nice. However, I would not stay there again due to air quality in the rooms and hallway."

Reviewed on Aug 3, 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

Orbitz is your one stop for guaranteed low prices on Middlesex County flights, as well as budget deals on hotels and rental cars. Use our state of the art mobile tools to get great deals and constant updates on the status of your trip.

Save Big On Car Rentals Too

Orbitz will find you discount air fare for flights to Middlesex County and you can rent a car at the same time. With Orbitzyou will get a discount on the rental and have your car waiting for you when you land.

Get Free Travel Advice By Calling the Orbitz Hotline

Our experts will make things even easier by helping you to find the best budget flights to Middlesex County Just call our toll free hotline at 1-800-649-9920 and one of our travel advisors will be happy to assist you with everything from your flight to hotel room.

Book Travel on the Fly with Orbitz on the Go

Our state of the art mobile apps will allow you to book cheap flights to Middlesex County from your smartphone too. Discount airfare is not all; you can also find mobile-only hotel deals or check the status of your flight using this free app. So, when you’re on the go, why not take Orbitz with you?

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 $98 and $603. 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.