$165 Cheap Flights to Middletown, NY

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How much is the cheapest flight to Middletown?

Prices were available within the past 7 days and start at $165 for one-way flights and $243 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fly Play
Sat, Nov 23 - Mon, Dec 2
KEF
Keflavik Intl.
SWF
Stewart Intl.
$243 Roundtrip, found 3 days ago
$243
Roundtrip
found 3 days ago
Select Fly Play flight, departing Sat, Nov 23 from Keflavik Intl. to Stewart Intl., returning Mon, Dec 2, priced at $243 found 3 days ago
Fly Play
Fri, Sep 27 - Thu, Oct 10
DUB
Dublin
SWF
Stewart Intl.
$279 Roundtrip, found 5 days ago
$279
Roundtrip
found 5 days ago
Select Fly Play flight, departing Fri, Sep 27 from Dublin to Stewart Intl., returning Thu, Oct 10, priced at $279 found 5 days ago
Fly Play
Thu, Sep 26 - Sun, Sep 29
CDG
Roissy-Charles de Gaulle
SWF
Stewart Intl.
$287 Roundtrip, found 9 hours ago
$287
Roundtrip
found 9 hours ago
Select Fly Play flight, departing Thu, Sep 26 from Roissy-Charles de Gaulle to Stewart Intl., returning Sun, Sep 29, priced at $287 found 9 hours ago
Fly Play
Fri, Sep 20 - Fri, Sep 27
CPH
Kastrup
SWF
Stewart Intl.
$292 Roundtrip, found 22 hours ago
$292
Roundtrip
found 22 hours ago
Select Fly Play flight, departing Fri, Sep 20 from Kastrup to Stewart Intl., returning Fri, Sep 27, priced at $292 found 22 hours ago
Fly Play
Mon, Jan 20 - Thu, Jan 30
MAD
Adolfo Suárez Madrid-Barajas
SWF
Stewart Intl.
$306 Roundtrip, found 3 days ago
$306
Roundtrip
found 3 days ago
Select Fly Play flight, departing Mon, Jan 20 from Adolfo Suárez Madrid-Barajas to Stewart Intl., returning Thu, Jan 30, priced at $306 found 3 days ago

Find Your Flights to Middletown POU

Cheap flights to Middletown (POU)

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.

We recommend using the ‘Flexible Dates’ calendar at the top of the page to see the price of plane tickets on the surrounding dates. This allows you to pick the cheapest days to fly if your trip allows flexibility and score cheap flight deals to Middletown.

Roundtrip prices range from $243 - $306, and one-ways to Middletown start as low as $165.

Be aware that choosing a non-stop flight can sometimes be more expensive while saving you time. And routes with connections may be available at a cheaper rate.

Airlines that fly to Middletown (POU)

You have several options for which airline you choose to travel with to Middletown. There are 10 airlines flying into POU: Fly Play. 

Cheap plane tickets may be available from different airlines at different times and with unique terms. It’s best to understand the details of each airline’s offer before judging its value.

For example, if you plan to check a bag or bring a carry-on, check whether the cheap airfare deal includes a baggage allowance. If not, verify whether the baggage fee is higher than the difference of other airline plane ticket deals offering free checked/carry-on baggage in exchange for a slightly higher airfare. 

Additionally, your preferred frequent flyer membership programs may influence your choice of cheap airline. Expedia allows you to enter your membership numbers during checkout to earn points from your airline and Expedia Rewards—all while getting a great deal and planning all your travel in one online platform.

Find the best deals

At Expedia, we source many flight deals from multiple providers, so you can easily find the best deals that are right for you. A great strategy for getting the best deals can be to make sure you book and travel at the optimal times. Airfare to Middletown (POU) varies throughout the year based on seasonal demand. You’ll see the lowest rates for roundtrips to POU in November and in December for one-ways.

Cancellation & flexibility

To change or cancel eligible flights, go to ‘My Trips’ and navigate to your itinerary. If you booked within the last 24-hours, you might be able to cancel your flight for free. Learn more about flight changes or cancellations from our customer service portal. Some plane tickets are available with no change fees, which you can filter for during your search.

Frequently asked questions

How do I find cheap flights to Middletown that have flexible change policies?
At Expedia, we’ve been channeling our inner Olympic gymnast to give you the most flexible airfares available. Simply tick the “No change fee” box directly underneath the “Flexible change policies” heading to find your perfect flight to Middletown.
What is the name of the airport in Middletown?
Book a flight to Middletown and you’ll be arriving at Stewart Intl. Airport (SWF).
Which day of the week is the best day to buy a plane ticket to Middletown?
Sunday is the best day of the week to purchase plane tickets. But there’s more than one way to score a terrific deal. Searching for tickets and being ready to buy several weeks before your departure date will also pay off. Research shows that the optimal booking window for cheap plane tickets ranges from 21 days to about 45 days prior to departure. Settled on your travel dates to Middletown well ahead of time? Monitor when carriers first release their tickets as these are often the lowest fares available. Savings are subject to change and may vary depending on selections made.
What airport is best to fly into Middletown?
There are two major airports that operate in Middletown. EWR is around 85 mi from downtown, while Stewart Intl. Airport (SWF) is approximately 30 mi away. As soon as you find a great price and work out where you’re staying, you’ll better know which to touchdown at.
Which airlines fly to Middletown?
From takeoff to arrival, you can look forward to a comfortable flight with United Airlines. One of 30 airlines that connects Middletown with 161 airports across the globe, it operates the biggest number of services between Orlando and Middletown. Spirit Airlines is another sought-after choice with many travelers.
How many nonstop flights are there to Middletown?
Flying to somewhere new is much more straightforward when there aren’t any stopovers to worry about. If you’re traveling to Middletown, the great news is that there are approximately 3,427 direct flights each week.
Where are the most popular flights to Middletown departing from?
Travelers frequently depart from Orlando, Toronto and Fort Lauderdale airports when heading to Middletown.
Do you have any tips for my flight to Middletown?

  • What you pack in your carry-on bag can make the difference between a comfortable flight, and a restless one. Start with the essentials, such as your passport (or a valid ID) and your travel documents. Once they’re packed, toss in any medications you might need. Next, think about comfort factor. Earphones, a quality neck pillow and a novel will help the hours fly by while you’re cruising at altitude.
  • You’ll also want to check with your airline regarding what you can’t bring on board your flight. Knives, razor blades, swords and batons are among the prohibited items. Anything flammable, explosive or sharp is generally not allowed in your carry-on bags. Remember to pack any sports equipment like baseball bats or tennis rackets only in your checked luggage.

What to wear on a flight:

  • Whether traveling long or short-haul, layering up is key to staying comfortable. Opt for loose, natural fabrics that will keep you fresh and bring a pullover to cope with any changes in cabin temperatures. Your feet will be happiest in a pair of closed-toe shoes or sneakers.
  • Consider wearing compression socks or tights to help prevent deep vein thrombosis (DVT). This condition is a result of blood clotting that can be caused by prolonged periods of sitting, especially on long-haul flights. Performing foot and leg stretches in your seat or wandering around the cabin are good ways to improve your circulation.

How can I get a cheap last-minute flight to Middletown?
The key to finding a cheap, spur-of-the-moment flight to Middletown is being flexible. You can nab a terrific deal if you’re not tied to specific travel dates, flight times and airlines. Also compare the prices of flying out of and into nearby airports if that’s an option for you.
Where can I learn more about changing or canceling my flight to Middletown?
Most flights are free to cancel within 24 hours of making the reservation. However, some flights are non-refundable, and you may receive a flight credit from the airline to use for a future booking. For more information, please visit our Customer Service Portal.
Flights to Middletown information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Destination city name
Newburgh
Roundtrip price
$242
*Available to One Key members.