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Westport

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Westport Flights as Low as $227

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

American Airlines
Tue, Jun 3 - Tue, Jun 10
TPA
Tampa Intl.
HPN
Westchester County
$227 Roundtrip, found 3 days ago
$227
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Jun 3 from Tampa Intl. to Westchester County, returning Tue, Jun 10, priced at $227 found 3 days ago
Delta
Tue, Jun 3 - Tue, Jun 10
TPA
Tampa Intl.
HPN
Westchester County
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jun 3 from Tampa Intl. to Westchester County, returning Tue, Jun 10, priced at $237 found 3 days ago
American Airlines
Tue, Jun 3 - Tue, Jun 10
TPA
Tampa Intl.
HPN
Westchester County
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Jun 3 from Tampa Intl. to Westchester County, returning Tue, Jun 10, priced at $237 found 3 days ago
Breeze Airways
Sun, Apr 13 - Thu, Apr 17
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$237 Roundtrip, found 11 hours ago
$237
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Sun, Apr 13 from Tampa Intl. to Tweed - New Haven Regional, returning Thu, Apr 17, priced at $237 found 11 hours ago
Delta
Wed, Jun 4 - Wed, Jun 11
TPA
Tampa Intl.
HPN
Westchester County
$239 Roundtrip, found 3 days ago
$239
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jun 4 from Tampa Intl. to Westchester County, returning Wed, Jun 11, priced at $239 found 3 days ago
Delta
Wed, Jun 4 - Wed, Jun 11
TPA
Tampa Intl.
HPN
Westchester County
$240 Roundtrip, found 3 days ago
$240
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jun 4 from Tampa Intl. to Westchester County, returning Wed, Jun 11, priced at $240 found 3 days ago
Breeze Airways
Sun, Apr 13 - Thu, Apr 17
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$242 Roundtrip, found 11 hours ago
$242
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Sun, Apr 13 from Tampa Intl. to Tweed - New Haven Regional, returning Thu, Apr 17, priced at $242 found 11 hours ago
American Airlines
Wed, Jun 4 - Wed, Jun 11
TPA
Tampa Intl.
HPN
Westchester County
$245 Roundtrip, found 3 days ago
$245
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Jun 4 from Tampa Intl. to Westchester County, returning Wed, Jun 11, priced at $245 found 3 days ago
American Airlines
Tue, Jun 3 - Tue, Jun 10
TPA
Tampa Intl.
HPN
Westchester County
$247 Roundtrip, found 3 days ago
$247
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Jun 3 from Tampa Intl. to Westchester County, returning Tue, Jun 10, priced at $247 found 3 days ago
Breeze Airways
Sun, Apr 13 - Thu, Apr 17
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$247 Roundtrip, found 11 hours ago
$247
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Sun, Apr 13 from Tampa Intl. to Tweed - New Haven Regional, returning Thu, Apr 17, priced at $247 found 11 hours ago
Breeze Airways
Sun, Apr 13 - Thu, Apr 17
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$251 Roundtrip, found 11 hours ago
$251
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Sun, Apr 13 from Tampa Intl. to Tweed - New Haven Regional, returning Thu, Apr 17, priced at $251 found 11 hours ago
Delta
Tue, Jun 3 - Tue, Jun 10
TPA
Tampa Intl.
HPN
Westchester County
$252 Roundtrip, found 3 days ago
$252
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jun 3 from Tampa Intl. to Westchester County, returning Tue, Jun 10, priced at $252 found 3 days ago
American Airlines
Wed, Jun 4 - Wed, Jun 11
TPA
Tampa Intl.
HPN
Westchester County
$256 Roundtrip, found 3 days ago
$256
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Jun 4 from Tampa Intl. to Westchester County, returning Wed, Jun 11, priced at $256 found 3 days ago
Delta
Tue, Jun 3 - Tue, Jun 10
TPA
Tampa Intl.
HPN
Westchester County
$268 Roundtrip, found 3 days ago
$268
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jun 3 from Tampa Intl. to Westchester County, returning Tue, Jun 10, priced at $268 found 3 days ago
American Airlines
Tue, Jun 3 - Tue, Jun 10
TPA
Tampa Intl.
HPN
Westchester County
$272 Roundtrip, found 3 days ago
$272
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Jun 3 from Tampa Intl. to Westchester County, returning Tue, Jun 10, priced at $272 found 3 days ago
JetBlue Airways
Wed, Jun 4 - Wed, Jun 11
TPA
Tampa Intl.
HPN
Westchester County
$276 Roundtrip, found 3 days ago
$276
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Jun 4 from Tampa Intl. to Westchester County, returning Wed, Jun 11, priced at $276 found 3 days 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 June, 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 $227, 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 $227 right now, why wait?

Westport Flight Information
Destination airport
MacArthur
Destination airport IATA code
ISP
Roundtrip price
$98

Last Minute Hotel Deals in Westport

Amsterdam Hotel
Amsterdam Hotel
2 out of 5
19 Clarks Hill Ave, Stamford, CT
The price is $116 per night from Apr 2 to Apr 3
$116
includes taxes & fees
Apr 2 - Apr 3
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! (1,578 reviews)
"Easy access. Great staff"

Reviewed on Mar 25, 2025

Amsterdam Hotel
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 $134 per night from Apr 2 to Apr 3
$134
includes taxes & fees
Apr 2 - Apr 3
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! (1,008 reviews)
"Good location."

Reviewed on Mar 28, 2025

EVEN Hotel Norwalk by IHG
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 $94 per night from Apr 28 to Apr 29
$94
includes taxes & fees
Apr 28 - Apr 29
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 ...
6.2/10 (385 reviews)
Good enough to sleep
"It is a no frills type of hotel. This is a place just for sleep, clean, safe, dated. Great location getting in and out of the highway and only 8min drive to/from the Stanford MTA station. The area itself is a little sketchy but mainly due to the industrial feel. Don’t expect much for your stay. You ..."

Reviewed on Mar 29, 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 $126 per night from Apr 23 to Apr 24
$126
includes taxes & fees
Apr 23 - Apr 24
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! (1,307 reviews)
Sort stay
"Bed was comfortable and the room was clean, would have been nice if there were eggs for breakfast"

Reviewed on Mar 26, 2025

The Circle Hotel Fairfield
Hyatt Regency Greenwich
Hyatt Regency Greenwich
4 out of 5
1800 E Putnam Avenue, Old Greenwich, CT
The price is $192 per night from Apr 13 to Apr 14
$192
includes taxes & fees
Apr 13 - Apr 14
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! (821 reviews)
"The room's bathroom and HVAC system needs updating."

Reviewed on Mar 25, 2025

Hyatt Regency Greenwich
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 7 to Apr 8
$137
includes taxes & fees
Apr 7 - Apr 8
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! (1,003 reviews)
"It was clean and price wa reasonable."

Reviewed on Mar 28, 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! (1,208 reviews)
"Very comfortable."

Reviewed on Mar 30, 2025

Norwalk Inn & Conference Center
Motel 6 Milford, CT
Motel 6 Milford, CT
2 out of 5
111 Schoolhouse Road, Milford, CT
The price is $85 per night from Apr 6 to Apr 7
$85
includes taxes & fees
Apr 6 - Apr 7
Book a stay at this business-friendly motel in Milford. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Silver Sands State Park ...
6.2/10 (1,003 reviews)
"Relaxing"

Reviewed on Mar 24, 2025

Motel 6 Milford, CT
See all 1,040 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.