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Westport

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Westport Flights as Low as $82

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Wed, Jul 9 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$82 Roundtrip, just found
$82
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Jul 9 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $82 just found
Breeze Airways
Wed, Jul 9 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$87 Roundtrip, just found
$87
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Jul 9 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $87 just found
Breeze Airways
Wed, Jul 9 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$92 Roundtrip, just found
$92
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Jul 9 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $92 just found
Avelo Airlines
Fri, Jun 13 - Mon, Jun 30
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$97 Roundtrip, found 1 hour ago
$97
Roundtrip
found 1 hour ago
Select Avelo Airlines flight, departing Fri, Jun 13 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Jun 30, priced at $97 found 1 hour ago
Breeze Airways
Fri, Jun 13 - Mon, Jun 30
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$99 Roundtrip, found 1 hour ago
$99
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Fri, Jun 13 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Jun 30, priced at $99 found 1 hour ago
Avelo Airlines
Fri, Jun 13 - Mon, Jun 30
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$102 Roundtrip, found 1 hour ago
$102
Roundtrip
found 1 hour ago
Select Avelo Airlines flight, departing Fri, Jun 13 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Jun 30, priced at $102 found 1 hour ago
Breeze Airways
Fri, Jun 13 - Mon, Jun 30
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$103 Roundtrip, found 1 hour ago
$103
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Fri, Jun 13 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Jun 30, priced at $103 found 1 hour ago
Breeze Airways
Fri, Jun 13 - Mon, Jun 30
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$104 Roundtrip, found 1 hour ago
$104
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Fri, Jun 13 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Jun 30, priced at $104 found 1 hour ago
Breeze Airways
Sat, Jun 14 - Wed, Jul 2
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$107 Roundtrip, found 1 hour ago
$107
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Jun 14 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Jul 2, priced at $107 found 1 hour ago
Breeze Airways
Fri, Jun 13 - Mon, Jun 30
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$109 Roundtrip, found 1 hour ago
$109
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Fri, Jun 13 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Jun 30, priced at $109 found 1 hour ago
Frontier Airlines
Tue, Aug 19 - Wed, Aug 27
MCO
Orlando Intl.
ISP
MacArthur
$149 Roundtrip, found 3 hours ago
$149
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Tue, Aug 19 from Orlando Intl. to MacArthur, returning Wed, Aug 27, priced at $149 found 3 hours ago
Breeze Airways
Thu, Jun 12 - Fri, Jun 13
MCO
Orlando Intl.
HPN
Westchester County
$176 Roundtrip, found 2 days ago
$176
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jun 12 from Orlando Intl. to Westchester County, returning Fri, Jun 13, priced at $176 found 2 days ago
JetBlue Airways
Tue, Jun 17 - Tue, Jun 24
MCO
Orlando Intl.
HPN
Westchester County
$181 Roundtrip, found 1 hour ago
$181
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Tue, Jun 17 from Orlando Intl. to Westchester County, returning Tue, Jun 24, priced at $181 found 1 hour ago
American Airlines
Tue, Aug 26 - Sun, Aug 31
ATL
Hartsfield-Jackson Atlanta Intl.
HPN
Westchester County
$192 Roundtrip, found 17 hours ago
$192
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Tue, Aug 26 from Hartsfield-Jackson Atlanta Intl. to Westchester County, returning Sun, Aug 31, priced at $192 found 17 hours ago
Delta
Tue, Aug 26 - Sun, Aug 31
ATL
Hartsfield-Jackson Atlanta Intl.
HPN
Westchester County
$197 Roundtrip, found 17 hours ago
$197
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Aug 26 from Hartsfield-Jackson Atlanta Intl. to Westchester County, returning Sun, Aug 31, priced at $197 found 17 hours ago
Frontier Airlines
Mon, Jun 23 - Thu, Jun 26
ATL
Hartsfield-Jackson Atlanta Intl.
ISP
MacArthur
$286 Roundtrip, found 1 hour ago
$286
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Jun 23 from Hartsfield-Jackson Atlanta Intl. to MacArthur, returning Thu, Jun 26, priced at $286 found 1 hour ago

Cheap Flights to Westport

Fall in love at first flight with your vacation to Westport by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Westport on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Westport, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Westport

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Westport with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the HPN airport.

What is the cheapest month to fly to Westport?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Westport are in July, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Westport?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Westport.

What airport is best to fly into Westport?

When you’re planning your trip to Westport, convenience is the name of the game. Luckily, Westport Igor I. Sikorsky Memorial Airport is nearby so you can deplane and get going on checking off everything on your Westport must-do list.

How much are flights to Westport?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Westport on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $82, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Westport?

The trick to saving a stack of cash on your flight to Westport? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $82 right now, why wait?

Westport Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$81

Last Minute Hotel Deals in Westport

Inn at Longshore
Inn at Longshore
2.5 out of 5
260 Compo Rd S, Westport, CT
Book a stay at this golf hotel in Westport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (142 reviews)
"The location was beautiful, the staff was great, and it almost felt like staying with a friend. Loved my stay... Also I'm craving the cinnamon scones from breakfast. Yum!"

Reviewed on May 20, 2025

Get rates
Inn at Longshore
EVEN Hotel Norwalk by IHG
EVEN Hotel Norwalk by IHG
3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
Stay at this 3.5-star business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,001 reviews)
"Great check-in process. Staff was friendly!"

Reviewed on May 28, 2025

Get rates
EVEN Hotel Norwalk by IHG
Amsterdam Hotel
Amsterdam Hotel
2 out of 5
19 Clarks Hill Ave, Stamford, CT
Book a stay at this business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (1,594 reviews)
"The rooms were large and comfortable. Close off highway 95 and food available within walking distance. Very convenient."

Reviewed on May 27, 2025

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Amsterdam Hotel
Hyatt Regency Greenwich
Hyatt Regency Greenwich
4 out of 5
1800 E Putnam Avenue, Old Greenwich, CT
Book a stay at this eco-certified hotel in Old Greenwich. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (922 reviews)
"Great"

Reviewed on May 29, 2025

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Hyatt Regency Greenwich
The Stamford Hotel
The Stamford Hotel
3.5 out of 5
700 East Main Street, Stamford, CT
Stay at this 3.5-star business-friendly hotel in Stamford. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff ...
7.6/10 Good! (1,040 reviews)
Great place!
"This hotel was wonderful. Very clean and excellent service. We also loved the food. The only downfall was that the downtown location is pretty noisy at night. This might be okay for many people, but I’m not used to the city noises."

Reviewed on May 25, 2025

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The Stamford Hotel
La Quinta Inn & Suites by Wyndham Stamford / New York City
La Quinta Inn & Suites by Wyndham Stamford / New York City
3 out of 5
135 Harvard Avenue, Stamford, CT
Stay at this 3-star business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6.4/10 (501 reviews)
"Clean great amenities.great pricing"

Reviewed on May 29, 2025

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La Quinta Inn & Suites by Wyndham Stamford / New York City
The Watershed
The Watershed
3.5 out of 5
353 Main Ave, Norwalk, CT
Stay at this 3.5-star business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,000 reviews)
Best hotel option in the Norwalk area
"We stayed here about 18 months ago prior to renovation. We were back and really enjoyed the new look and accommodations. The rooms were well appointed, very clean and comfortable. The quality of the bedding and shower were characteristic of a premium hotel. Would recommend for those who visit the ..."

Reviewed on May 28, 2025

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The Watershed
Ethan Allen Hotel
Ethan Allen Hotel
3.5 out of 5
21 Lake Avenue Extension, I-84 at Exit 4, Danbury, CT
Stay at this 3.5-star business-friendly hotel in Danbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (1,009 reviews)
"The restaurant food and bar tender are awful."

Reviewed on May 26, 2025

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Ethan Allen Hotel
See all 1,053 properties in Westport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.