Cheap Flights to Middletown, VA

Popular airlines to Middletown

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Frequently asked questions

What month is the cheapest to fly to Middletown?
is the cheapest month to fly to Middletown. Demand is lower then, so you're likely to get a good deal. Planning your trip outside of school breaks and major holidays could also help you save.
Which US cities have the cheapest flights to Middletown?
Land cheap flights to Middletown from Boston, Chicago and Atlanta. These cities generally offer the lowest fares to this unique destination. But bear in mind that holiday periods, stopovers and demand also influence rates, so remain flexible and book when prices are right.
Which US cities fly direct to Middletown?
You can fly to Middletown without any stops from 92 US destinations. To find a nonstop route, select "Direct flights only" when searching for flights to Middletown on Expedia. Then, explore the options and find the best departure from one of these cities:

  • Boston
  • Chicago
  • Atlanta
  • New York
  • Orlando

How to find a cheap flight to Middletown?
Book early to snag cheap flights to Middletown. Also, consider traveling during off-peak months like January and February. If you jet off on a Thursday, you'll save 16% on average compared to departing on a Sunday.* Save time checking every day and track your flight prices using the Expedia app. We'll let you know when fares change.*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 Middletown?
Although booking in advance is usually the easiest way to save cash, don't worry if your Middletown trip is last minute. It's still possible to find cheap flights to Middletown, especially if your plans have a little wiggle room. Try switching up your travel dates, looking at different ticket types or jetting out of another airport.
How far in advance should I book a flight to Middletown?
To pick up the best deals on domestic journeys, book your flight to Middletown 28 days ahead of your travel dates. For international flights, it's between two and four months in advance. This boosts your chances of securing the departure dates and seats you want.**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 Middletown?
You can usually get cheap flights to Middletown on Sundays. You can save about 8% on average compared to those who book on a Friday, which is often the most expensive day for tickets.**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 Middletown?
A total of 38 carriers connect 125 airports all over the world to Middletown. Here are a few of the key airlines to Middletown, where Washington Dulles Intl. Airport (IAD) is the major gateway:

  • United Airlines
  • Delta Air Lines
  • American Airlines
  • Southern Airways Express

Where do you fly into Middletown?
When you're flying to Middletown, the main airport to touch down at is Washington Dulles Intl. Airport (IAD). You can also head to nearby hubs like Hagerstown Regional Airport (HGR), Charlottesville-Albemarle Airport (CHO) or Front Royal, VA (FRR-Front Royal - Warren County). Another great option to think about when you fly to Middletown is Winchester, VA (WGO-Winchester Regional).
How far is the airport from central Middletown?
You'll be around 45 mi east of the center of Middletown after touching down at Washington Dulles Intl. Airport (IAD).
Can I save money by booking a Middletown trip package?
Bundle your flight and hotel and you could save hundreds of dollars. What's more, you can add extras like activities and car rentals to your Middletown flight and hotel package deal. With Expedia, it's easy to book all your Middletown travel arrangements in one place.
Can I change or cancel my flight to Middletown?
If you booked your flight to Middletown within the last 24 hours, you can typically change or cancel it without fees. After that, additional costs may apply depending on the airline's rules and restrictions. For more information, head to our Customer Service Portal. Bear in mind that some flights are non-refundable, so you may be offered a credit toward a future flight rather than a direct refund. During your search on Expedia, use the "No cancel fee" or "Changes included" filters to compare tickets with flexible change policies.

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Tips to find the cheapest flights to Middletown

The cheapest day to fly

Get started finding a cheap flight to Middletown 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

is the cheapest month to fly to Middletown. 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 Middletown. 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 Middletown, 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 Middletown

The lowest price for round-trip flights to Middletown in 2025 starts from , while one-way tickets start from . 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 Middletown. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Middletown

are just some of the airlines that can typically offer cheap tickets to Middletown. 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 Middletown and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Middletown, 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 Middletown. 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 Middletown 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 Middletown

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 Middletown.

Stopover savings

The cheapest tickets to Middletown are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Middletown. 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 Middletown 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 Middletown. Simply download the free Expedia app to your smart device and activate Middletown 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 Middletown. 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.

Tips to find the cheapest flights to Middletown

Travel information

Destination airport
Middletown
Destination airport IATA code
WGO

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*Available to One Key members.