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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
Thu, Jul 10 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$82 Roundtrip, found 1 day ago
$82
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jul 10 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $82 found 1 day ago
Breeze Airways
Thu, Jul 10 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$87 Roundtrip, found 1 day ago
$87
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jul 10 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $87 found 1 day ago
Breeze Airways
Thu, Jul 10 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$92 Roundtrip, found 1 day ago
$92
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jul 10 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $92 found 1 day ago
Frontier Airlines
Tue, May 13 - Sun, May 18
MCO
Orlando Intl.
ISP
MacArthur
$94 Roundtrip, found 5 days ago
$94
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, May 13 from Orlando Intl. to MacArthur, returning Sun, May 18, priced at $94 found 5 days ago
Frontier Airlines
Wed, May 14 - Sun, May 18
MCO
Orlando Intl.
ISP
MacArthur
$96 Roundtrip, found 5 days ago
$96
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, May 14 from Orlando Intl. to MacArthur, returning Sun, May 18, priced at $96 found 5 days ago
Frontier Airlines
Tue, May 13 - Tue, May 13
MCO
Orlando Intl.
ISP
MacArthur
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, May 13 from Orlando Intl. to MacArthur, returning Tue, May 13, priced at $98 found 1 day ago
Frontier Airlines
Wed, Apr 30 - Sun, May 4
MCO
Orlando Intl.
ISP
MacArthur
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Apr 30 from Orlando Intl. to MacArthur, returning Sun, May 4, priced at $100 found 2 days ago
Frontier Airlines
Thu, May 1 - Thu, May 8
MCO
Orlando Intl.
ISP
MacArthur
$108 Roundtrip, found 2 days ago
$108
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, May 1 from Orlando Intl. to MacArthur, returning Thu, May 8, priced at $108 found 2 days ago
Frontier Airlines
Wed, Apr 30 - Thu, May 8
MCO
Orlando Intl.
ISP
MacArthur
$110 Roundtrip, found 2 days ago
$110
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Apr 30 from Orlando Intl. to MacArthur, returning Thu, May 8, priced at $110 found 2 days ago
Frontier Airlines
Fri, Apr 25 - Mon, Apr 28
MCO
Orlando Intl.
ISP
MacArthur
$115 Roundtrip, found 4 days ago
$115
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Apr 25 from Orlando Intl. to MacArthur, returning Mon, Apr 28, priced at $115 found 4 days ago
JetBlue Airways
Fri, May 2 - Sun, May 4
MCO
Orlando Intl.
ISP
MacArthur
$125 Roundtrip, found 2 days ago
$125
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, May 2 from Orlando Intl. to MacArthur, returning Sun, May 4, priced at $125 found 2 days ago
Frontier Airlines
Mon, Apr 28 - Sun, May 4
MCO
Orlando Intl.
ISP
MacArthur
$130 Roundtrip, found 2 days ago
$130
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Apr 28 from Orlando Intl. to MacArthur, returning Sun, May 4, priced at $130 found 2 days ago
JetBlue Airways
Tue, May 13 - Tue, May 13
MCO
Orlando Intl.
ISP
MacArthur
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, May 13 from Orlando Intl. to MacArthur, returning Tue, May 13, priced at $142 found 1 day ago
Breeze Airways
Fri, May 16 - Sun, May 18
MCO
Orlando Intl.
HPN
Westchester County
$153 Roundtrip, just found
$153
Roundtrip
just found
Select Breeze Airways flight, departing Fri, May 16 from Orlando Intl. to Westchester County, returning Sun, May 18, priced at $153 just found
Delta
Fri, May 16 - Sat, May 17
MCO
Orlando Intl.
HPN
Westchester County
$230 Roundtrip, found 1 day ago
$230
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, May 16 from Orlando Intl. to Westchester County, returning Sat, May 17, priced at $230 found 1 day ago
American Airlines
Fri, May 16 - Sun, May 18
MCO
Orlando Intl.
HPN
Westchester County
$261 Roundtrip, just found
$261
Roundtrip
just found
Select American Airlines flight, departing Fri, May 16 from Orlando Intl. to Westchester County, returning Sun, May 18, priced at $261 just found

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
Westchester County
Destination airport IATA code
HPN
Roundtrip price
$190

Last Minute Hotel Deals in Westport

EVEN Hotel Norwalk by IHG
EVEN Hotel Norwalk by IHG
3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
The price is $116 per night from Apr 20 to Apr 21
$116
includes taxes & fees
Apr 20 - Apr 21
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)
"It was pretty gd"

Reviewed on Apr 15, 2025

EVEN Hotel Norwalk by IHG
Amsterdam Hotel
Amsterdam Hotel
2 out of 5
19 Clarks Hill Ave, Stamford, CT
The price is $116 per night from Apr 18 to Apr 19
$116
includes taxes & fees
Apr 18 - Apr 19
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! (1,575 reviews)
"Eric S."

Reviewed on Apr 11, 2025

Amsterdam Hotel
Hyatt Regency Greenwich
Hyatt Regency Greenwich
4 out of 5
1800 E Putnam Avenue, Old Greenwich, CT
The price is $192 per night from May 1 to May 2
$192
includes taxes & fees
May 1 - May 2
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! (836 reviews)
"Great staff, bar was fantastic."

Reviewed on Apr 13, 2025

Hyatt Regency Greenwich
La Quinta Inn & Suites by Wyndham Stamford / New York City
La Quinta Inn & Suites by Wyndham Stamford / New York City
2.5 out of 5
135 Harvard Avenue, Stamford, CT
The price is $100 per night from May 18 to May 19
$100
includes taxes & fees
May 18 - May 19
Book a stay at this 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 (419 reviews)
Overall - it was a good stay.
"Staff was very friendly and attentive. Room was clean and bed was comfortable. Breakfast was good. Biscuits, eggs and make your own waffles. It was close to NY city, which is why we stayed. The only negative, was the elevator was broken. But guest were allowed to use the employee servive ..."

Reviewed on Apr 14, 2025

La Quinta Inn & Suites by Wyndham Stamford / New York City
The Circle Hotel Fairfield
The Circle Hotel Fairfield
3 out of 5
417 Post Road, Fairfield, CT
The price is $171 per night from Apr 20 to Apr 21
$171
includes taxes & fees
Apr 20 - Apr 21
Stay at this 3-star beach hotel in Fairfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
8.8/10 Excellent! (1,329 reviews)
"Wonderful front desk very accommodating"

Reviewed on Apr 16, 2025

The Circle Hotel Fairfield
Hyatt Place Milford / New Haven
Hyatt Place Milford / New Haven
3 out of 5
190 Old Gate Lane, Milford, CT
The price is $137 per night from Apr 23 to Apr 24
$137
includes taxes & fees
Apr 23 - Apr 24
Stay at this 3-star business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,002 reviews)
"The staff was very attentive and super helpful"

Reviewed on Apr 15, 2025

Hyatt Place Milford / New Haven
Norwalk Inn & Conference Center
Norwalk Inn & Conference Center
4 out of 5
99 East Avenue, Norwalk, CT
The price is $154 per night from Apr 20 to Apr 21
$154
includes taxes & fees
Apr 20 - Apr 21
Stay at this 4-star hotel in Norwalk. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the bar in our reviews. Popular ...
8.6/10 Excellent! (1,219 reviews)
"Decent facilities, not too far walking from restaurants and shops."

Reviewed on Apr 14, 2025

Norwalk Inn & Conference Center
The Stamford Hotel
The Stamford Hotel
3.5 out of 5
700 East Main Street, Stamford, CT
The price is $173 per night from Apr 24 to Apr 25
$173
includes taxes & fees
Apr 24 - Apr 25
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 ...
7.8/10 Good! (1,016 reviews)
"Great short stay! We will be back!"

Reviewed on Apr 15, 2025

The Stamford Hotel
See all 1,028 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.