$37 Cheap Flights to Middlebury, CT

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How much is the cheapest flight to Middlebury?

Prices were available within the past 7 days and start at $37 for one-way flights and $74 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Avelo Airlines
Avelo Airlines
Avelo Airlines
Avelo Airlines
Breeze Airways

Tips to find the cheapest flights to Middlebury

The cheapest day to fly

Get started finding a cheap flight to Middlebury on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

The cheapest month to fly

July is the cheapest month to fly to Middlebury. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Middlebury. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute.

The most affordable time to book a flight

Typically, a Sunday can be the cheapest time to book a flight to Middlebury, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation.

The cheapest round-trip tickets to Middlebury

The lowest price for round-trip flights to Middlebury in 2025 starts from from $74, while one-way tickets start from from $37. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Middlebury. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Middlebury

Avelo Airlines, Breeze Airways are just some of the airlines that can typically offer cheap tickets to Middlebury. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Middlebury and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Middlebury, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Middlebury. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia.

Save with a package

With Expedia's amazing package deals, you could save hundreds of dollars by booking your Middlebury plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving.

Date flexibility for the cheapest flights to Middlebury

If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Middlebury.

Stopover savings

The cheapest tickets to Middlebury are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Middlebury. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved.

Get Expedia's Price Drop Protection

Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference*. This gives you peace of mind that you're getting one of the cheapest flights to Middlebury for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members.

*Terms apply.

Use our Price Tracking feature

Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Middlebury. Simply download the free Expedia app to your smart device and activate Middlebury flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices.

Book with Expedia

As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Middlebury. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

What month is the cheapest to fly to Middlebury?
July is usually the least expensive month for flights to Middlebury*. Look out for affordable flights during this time as you could snag a good deal. *Cheapest month to fly is based on the month with the cheapest flight found on Expedia.com in the next 330 days.
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.
Flights to Middlebury information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Destination city name
New Haven
Roundtrip price
$74

Trending flights to Middlebury

Prices were available within the past 7 days and start at $37 for one-way flights and $74 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Avelo Airlines

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*Available to One Key members.