$34 Cheap Flights to Westport, CT

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

Popular airlines to Westport

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

How much is the cheapest flight to Westport?

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
Sat, May 23 - Tue, May 26
MCO
Orlando
HVN
New Haven
$73 Roundtrip, found 13 hours ago
$73
Roundtrip
found 13 hours ago
Select Avelo Airlines flight, departing Sat, May 23 from Orlando to New Haven, returning Tue, May 26, priced at $73 found 13 hours ago
Frontier Airlines
Sat, Jun 6 - Tue, Jun 9
MCO
Orlando
ISP
Islip
$88 Roundtrip, found 2 hours ago
$88
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Jun 6 from Orlando to Islip, returning Tue, Jun 9, priced at $88 found 2 hours ago
Breeze Airways
Thu, May 28 - Sat, May 30
MCO
Orlando
HVN
New Haven
$102 Roundtrip, found 7 hours ago
$102
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Thu, May 28 from Orlando to New Haven, returning Sat, May 30, priced at $102 found 7 hours ago
Delta
Wed, Apr 29 - Tue, May 19
MCO
Orlando
HPN
White Plains
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Apr 29 from Orlando to White Plains, returning Tue, May 19, priced at $197 found 5 days ago
American Airlines
Mon, Apr 27 - Sun, May 3
MCO
Orlando
HPN
White Plains
$205 Roundtrip, found 5 hours ago
$205
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Mon, Apr 27 from Orlando to White Plains, returning Sun, May 3, priced at $205 found 5 hours ago

Frequently asked questions

What month is the cheapest to fly to Westport?
Plan your trip for May 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.

*Flight schedules are subject to change.

*Available to One Key members.

 

Travel information

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

Trending flights to Westport

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
Sat, May 23 - Tue, May 26
MCO
Orlando
HVN
New Haven
$73 Roundtrip, found 13 hours ago
$73
Roundtrip
found 13 hours ago
Select Avelo Airlines flight, departing Sat, May 23 from Orlando to New Haven, returning Tue, May 26, priced at $73 found 13 hours ago

Explore a world of travel with Expedia