$34 Cheap Flights to Middlebury, CT

View $34 flight on Tue, Jun 9, 2026Opens in a new window

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Popular airlines to Middlebury

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How much is the cheapest flight to Middlebury?

Prices were available within the past 7 days and start at $34 for one-way flights and $73 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Avelo Airlines
Tue, Jun 9 - Sat, Jun 13
MCO
Orlando
HVN
New Haven
$73 Roundtrip, found 6 hours ago
$73
Roundtrip
found 6 hours ago
Select Avelo Airlines flight, departing Tue, Jun 9 from Orlando to New Haven, returning Sat, Jun 13, priced at $73 found 6 hours ago
Avelo Airlines
Thu, May 7 - Mon, May 11
TPA
Tampa
HVN
New Haven
$78 Roundtrip, found 1 hour ago
$78
Roundtrip
found 1 hour ago
Select Avelo Airlines flight, departing Thu, May 7 from Tampa to New Haven, returning Mon, May 11, priced at $78 found 1 hour ago
Avelo Airlines
Fri, Jun 5 - Fri, Jun 12
LAL
Lakeland
HVN
New Haven
$87 Roundtrip, found 3 hours ago
$87
Roundtrip
found 3 hours ago
Select Avelo Airlines flight, departing Fri, Jun 5 from Lakeland to New Haven, returning Fri, Jun 12, priced at $87 found 3 hours ago
Avelo Airlines
Fri, Aug 14 - Sat, Aug 22
TPA
Tampa
HVN
New Haven
$88 Roundtrip, found 3 days ago
$88
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Fri, Aug 14 from Tampa to New Haven, returning Sat, Aug 22, priced at $88 found 3 days ago
Breeze Airways
Thu, May 28 - Sun, May 31
MCO
Orlando
HVN
New Haven
$102 Roundtrip, just found
$102
Roundtrip
just found
Select Breeze Airways flight, departing Thu, May 28 from Orlando to New Haven, returning Sun, May 31, priced at $102 just found

Alternative airports near Middlebury

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Tweed - New Haven Regional HVN. Average driving time to city center is 41 minutes. Flights from $758
HVN
Tweed - New Haven Regional
Average driving time to city center41 min
Flights from $758

Frequently asked questions

What month is the cheapest to fly to Middlebury?
Plan your trip for June if you want to land a deal on your fare. It's the cheapest month to fly to Middlebury. Try to avoid traveling during peak periods such as major public holidays or during big events.
Which US cities have the cheapest flights to Middlebury?
Usually, Washington, Chicago and Orlando offer cheap flights to Middlebury. However, being flexible is always key to landing the best prices. Plan your escape during the off-peak season or midweek to keep costs as low as possible.
Which US cities fly direct to Middlebury?
Pick from 32 US cities that have direct flights to Middlebury. While booking on Expedia, check the "Direct flights only" box to compare nonstop routes. Fly to Middlebury from any of these cities:

  • Washington
  • Chicago
  • Orlando
  • Atlanta
  • Charlotte

How to find a cheap flight to Middlebury?
If you're eager to find cheap flights to Middlebury, consider traveling in the low season. Booking in advance is also likely to save you money. Or, look for departures on a different day — Thursday flights are on average 16% cheaper than Sunday departures.* Sign up to receive price alerts on the Expedia app and get notifications when fares fall.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Middlebury?
It's possible to get good deals on last-minute flights to Middlebury, especially if your travel plans aren't set in stone. Consider flying from a different hub, changing your trip dates or picking an alternative carrier to get a cheap flight to Middlebury.
How far in advance should I book a flight to Middlebury?
Lock in your flight to Middlebury two to four months ahead if you're visiting from an international destination. For domestic travel, the recommendation is around 28 days in advance. Lower prices and a wider variety of travel dates, schedules and seating options are just some of the perks of booking early.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Middlebury?
Sundays are generally the best day to book a cheap flight to Middlebury, with savings of around 8% on average compared to Fridays. If you decide to buy tickets on a Friday, expect to spend more as this is typically the most expensive day.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Middlebury?
A total of 10 carriers connect 34 airports all over the world to Middlebury. Here are some of the top airlines to Middlebury, where Bradley Intl. Airport (BDL) is the major gateway:

  • Delta Air Lines
  • American Airlines
  • United Airlines
  • JetBlue Airways

Where do you fly into Middlebury?
Middlebury's main gateway is Tweed - New Haven Regional Airport (HVN). If you want other nearby options when flying to Middlebury, check out Hartford, CT (HFD-Hartford - Brainard), Bradley Intl. Airport (BDL) or Westchester County Airport (HPN). You can also fly to Middlebury through MacArthur Airport (ISP).
How far is the airport from central Middlebury?
You'll be roughly 20 mi southeast of central Middlebury after jetting into Tweed - New Haven Regional Airport (HVN).
Can I save money by booking a Middlebury trip package?
Book a Middlebury flight and hotel package deal on Expedia, and you could benefit from significant savings. It's simple to bundle your accommodations and flights, and you can add activities and car rentals to create your own customized Middlebury vacation. Plus, there's nothing like the convenience of booking everything in one place.
Can I change or cancel my flight to Middlebury?
It's often possible to cancel or change your flight to Middlebury. Many airlines let you cancel your flights for free within 24 hours of making your booking. However, some flights are non-refundable, and airlines may issue you credit for a future flight in place of a direct refund. To secure affordable flights to Middlebury with flexible change policies, check the "No cancel fee" or "Changes included" filters during your search. Need more information? Head to our Customer Service Portal.

*Flight schedules are subject to change.

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Travel information

Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Destination city name
New Haven
Roundtrip price
$73

Trending flights to Middlebury

Prices were available within the past 7 days and start at $34 for one-way flights and $73 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Avelo Airlines
Tue, Jun 9 - Sat, Jun 13
MCO
Orlando
HVN
New Haven
$73 Roundtrip, found 6 hours ago
$73
Roundtrip
found 6 hours ago
Select Avelo Airlines flight, departing Tue, Jun 9 from Orlando to New Haven, returning Sat, Jun 13, priced at $73 found 6 hours ago

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