$29 Cheap Flights to Westport, CT

Popular airlines to Westport

How much is the cheapest flight to Westport?

Prices were available within the past 7 days and start at $29 for one-way flights and $58 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Breeze Airways
JetBlue Airways
Southwest Airlines
American Airlines

Find the cheapest month to fly from Columbus (CMH) to White Plains (HPN)

April is typically the cheapest month to fly

From $180 - $406 per traveler.

Alternative airports near Westport

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

Tips to find the cheapest flights to Westport

The cheapest day to fly

Get started finding a cheap flight to Westport 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

December is the cheapest month to fly to Westport. 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 Westport. 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 Westport, 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 Westport

The lowest price for round-trip flights to Westport in 2025 starts from from $58, while one-way tickets start from from $29. 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 Westport. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Westport

Frontier Airlines, Breeze Airways, JetBlue Airways, Southwest Airlines, American Airlines are just some of the airlines that can typically offer cheap tickets to Westport. 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 Westport and countless more destinations worldwide.

The most affordable airports to fly into

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

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 Westport.

Stopover savings

The cheapest tickets to Westport are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Westport. 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 Westport 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 Westport. Simply download the free Expedia app to your smart device and activate Westport 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 Westport. 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 Westport?
Plan your trip for December if you're looking for a good price on your fare. It's the cheapest month to fly to Westport. If possible, avoid traveling during busy periods such as public holidays or major events.
Which US cities have the cheapest flights to Westport?
Score cheap flights to Westport from Los Angeles, San Francisco and Boston. These cities generally offer the best fares to this top destination. But bear in mind that holiday periods, demand and stopovers will also have an impact on rates, so stay flexible and book when you spot a bargain.
Which US cities fly direct to Westport?
Pick from 58 US cities that have direct flights to Westport. While booking on Expedia, select the "Direct flights only" filter to compare nonstop options. Fly to Westport from any of these leading cities:

  • Los Angeles
  • San Francisco
  • Boston
  • Miami
  • Orlando

How to find a cheap flight to Westport?
Book your trip early to snag cheap flights to Westport. Also, consider traveling during off-peak months like February and June. If you jet off on a Thursday, you'll save an average of 16% compared to those departing on a Sunday.* Save time searching every day and create a price alert on the Expedia app. We'll let you know when fares drop.*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 Westport?
Staying flexible about your plans might help you to find last-minute deals on cheap flights to Westport. To view all the available options, try exploring different ticket types, tweaking your Westport trip dates, jetting out of an alternative airport or going with another airline.
How far in advance should I book a flight to Westport?
Get the travel dates you want and a price that works with your budget by booking your domestic flight to Westport up to 28 days in advance. Search for tickets two to four months ahead if you're flying to Westport from an international destination.**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 Westport?
You can save an average of 8% if you purchase tickets on a Sunday instead of Fridays, which tend to be the most expensive day to book.* When it comes to scoring a cheap flight to Westport, timing makes a difference.*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 Westport?
There are 72 airlines that connect Westport with 168 airports worldwide. The key point of arrival to this city is John F. Kennedy Intl. Airport (JFK). Book a fare with any of these popular airlines to Westport:

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

Where do you fly into Westport?
The main airport when you fly to Westport is Westchester County Airport (HPN), but there are other nearby options like Tweed - New Haven Regional Airport (HVN) and MacArthur Airport (ISP). You can also arrive at LaGuardia Airport (LGA) and John F. Kennedy Intl. Airport (JFK) when flying to Westport.
How far is the airport from central Westport?
You'll be roughly 19 mi west of the center of Westport after arriving at Westchester County Airport (HPN).
Can I save money by booking a Westport trip package?
Bundle your accommodations and flights and you could save hundreds of dollars. Better still, you can add extras like tours and car rentals to your Westport flight and hotel package deal. With Expedia, it's easy to organize all your Westport travel plans in the same place.
Can I change or cancel my flight to Westport?
It's usually possible to cancel or change your flight to Westport. Many airlines let you cancel your flight for free within 24 hours of booking. However, some flights are non-refundable, and airlines may issue you a credit toward a future trip instead of a direct refund. To secure affordable flights to Westport with flexible change policies, check "Changes included" or "No cancel fee" when you search. Need more information? Head to our Customer Service Portal.
Flights to Westport information
Destination airport
MacArthur
Destination airport IATA code
ISP
Destination city name
Islip
Roundtrip price
$57

Trending flights to Westport

Prices were available within the past 7 days and start at $29 for one-way flights and $58 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines

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*Available to One Key members.