Cheap Flights to Middlebury from $39

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How Much Does it Cost To Fly To Middlebury?

The cheapest prices found with in the last 7 days for return flights were $76 and $39 for one-way flights to Middlebury for the period specified. Prices and availability are subject to change. Additional terms apply

Sun, Aug 31 - Thu, Sep 4
CHS
Charleston Intl.
HVN
Tweed - New Haven Regional
$78 Roundtrip, found 1 day ago
$78
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, Aug 31 from Charleston Intl. to Tweed - New Haven Regional, returning Thu, Sep 4, priced at $78 found 1 day ago
OriginDestinationTravel DatesFlights From*
TPAEast HavenAugust 31 to September 4$76
MCOEast HavenSeptember 18 to September 21$82
LAXEast HavenOctober 22 to October 27$603
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCOEast HavenAugust 22 to August 24$158
TPAEast HavenAugust 22 to August 25$231
LAXEast HavenAugust 23 to August 26$644
*Prices include taxes and fees

Middlebury Flight Information

Traveling to
Middlebury
Lowest Price
$76
Number of Airlines Serving
Airlines Serving
Breeze Airways
Number of Daily Flights
Airlines with Direct Flights

Best Middlebury Flight and Hotel Packages

Middlebury flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
per person
Oct 9 - Oct 14
found 11 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
Courtyard by Marriott Southington

Courtyard by Marriott Southington

3 out of 5
per person
Oct 9 - Oct 14
found 11 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
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Need a Car For After Your Flight?

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

Which airlines fly to Middlebury?
Don't waste any time.Book your ticket to Middlebury now.There are 11carriers totake your pick of,including:

  • American Airlines
  • Delta Air Lines
  • Avelo Airlines

What airport is best to fly into Middlebury?
If you need to find accommodations in Middlebury only a short distance from where you land, bear in mind that the city is serviced by numerous airports. Be clear on which one you're flying in and out of. Here are the most popular:

  • BDL – 35 mi from downtown
  • Tweed - New Haven Regional Airport – 20 mi from downtown
  • Igor I. Sikorsky Memorial Airport (BDR) – 25 mi from downtown

Where to stay in Middlebury
With 34 fabulous accommodations in Middlebury, you're spoilt for choice. But don't wait around. The sooner you book, the sooner you can start your adventure!Searching for someplace to get some rest in Middlebury? The Tucker Hill Inn and the Hampton Inn Waterbury are our recommended accommodations in the region.
Places to visit in Middlebury
You're certain to have a day of fantastic fun at Quassy Amusement Park, a theme park that's popular with the locals. Want some more ideas? There's no better place to escape from the daily grind than Middlebury Center Historic District. Enjoy a book, kick a ball or simply have a picnic with friends and family in this idyllic urban sanctuary. But that's not all there is. Soak in nature's beauty on the shores of Lake Quassapaug.
How to get through airport security fast when traveling to Middlebury
These practical tips about airport security procedures will save you a lot of time and energy on your way to Middlebury:

  • Keep your travel ID and boarding pass within easy reach. They'll be the first things you'll be told to produce by airport security staff.
  • Remove your shoes and belt before approaching security. Items like these are not allowed in the body scanner.
  • Make sure your electronic devices and laptop are within easy reach. These items need to be put through the X-ray machine in separate trays.
  • When you get to the security checkpoint, you'll be asked to put all creams, liquids and gels in a separate tub for scanning. Make sure they're all stored in containers smaller than 3.4 ounces (100 milliliters) and sealed in a clear zip-lock bag.
  • Consider the type of footwear you want to fly in. Slippers are great because they're super easy to take off when you're at the security checkpoint. Try wearing some on your next flight!
  • Stash any pocketknives or other dangerous items in your checked luggage. Security personnel don't allow these on the aircraft.

Plane Tickets To Middlebury

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Middlebury. Browse through our inventory to explore a wide range of cheap flights to Middlebury to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Middlebury as you anxiously await to exit the plane and explore what Middlebury has to offer. Considering all the amazing local food and culture in Middlebury, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Middlebury to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Middlebury without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Middlebury with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Middlebury today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.