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Westport

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Westport Flights as Low as $160

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

Avelo Airlines
Thu, Jun 11 - Mon, Jun 15
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$160 Roundtrip, found 1 day ago
$160
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Thu, Jun 11 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Jun 15, priced at $160 found 1 day ago
Avelo Airlines
Thu, Jun 11 - Mon, Jun 15
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$167 Roundtrip, found 4 days ago
$167
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Thu, Jun 11 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Jun 15, priced at $167 found 4 days ago
Breeze Airways
Thu, Jul 30 - Sun, Aug 2
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$214 Roundtrip, found 2 hours ago
$214
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, Jul 30 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sun, Aug 2, priced at $214 found 2 hours ago
JetBlue Airways
Sat, May 16 - Sat, May 23
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$217 Roundtrip, found 8 hours ago
$217
Roundtrip
found 8 hours ago
Select JetBlue Airways flight, departing Sat, May 16 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Sat, May 23, priced at $217 found 8 hours ago
JetBlue Airways
Wed, May 20 - Tue, May 26
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$222 Roundtrip, found 22 hours ago
$222
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Wed, May 20 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Tue, May 26, priced at $222 found 22 hours ago
Breeze Airways
Thu, Jul 30 - Sun, Aug 2
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$224 Roundtrip, found 2 hours ago
$224
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, Jul 30 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sun, Aug 2, priced at $224 found 2 hours ago
Breeze Airways
Thu, Jul 30 - Sun, Aug 2
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$230 Roundtrip, found 2 hours ago
$230
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, Jul 30 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sun, Aug 2, priced at $230 found 2 hours ago
Delta
Sat, May 16 - Sat, May 23
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$237 Roundtrip, found 8 hours ago
$237
Roundtrip
found 8 hours ago
Select Delta flight, departing Sat, May 16 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Sat, May 23, priced at $237 found 8 hours ago
JetBlue Airways
Mon, May 18 - Tue, May 19
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$237 Roundtrip, found 22 hours ago
$237
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Mon, May 18 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Tue, May 19, priced at $237 found 22 hours ago
Avelo Airlines
Wed, Jul 29 - Thu, Jul 30
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$239 Roundtrip, found 6 days ago
$239
Roundtrip
found 6 days ago
Select Avelo Airlines flight, departing Wed, Jul 29 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Thu, Jul 30, priced at $239 found 6 days ago
Delta
Wed, May 20 - Tue, May 26
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$242 Roundtrip, found 22 hours ago
$242
Roundtrip
found 22 hours ago
Select Delta flight, departing Wed, May 20 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Tue, May 26, priced at $242 found 22 hours ago
Delta
Sat, May 16 - Sat, May 23
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$247 Roundtrip, found 8 hours ago
$247
Roundtrip
found 8 hours ago
Select Delta flight, departing Sat, May 16 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Sat, May 23, priced at $247 found 8 hours ago
American Airlines
Sat, May 16 - Sat, May 23
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$257 Roundtrip, found 8 hours ago
$257
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Sat, May 16 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Sat, May 23, priced at $257 found 8 hours ago
Frontier Airlines
Thu, Apr 30 - Mon, May 4
CLE
Hopkins Intl.
ISP
MacArthur
$262 Roundtrip, found 3 days ago
$262
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Hopkins Intl. to MacArthur, returning Mon, May 4, priced at $262 found 3 days ago
JetBlue Airways
Wed, May 13 - Sat, May 16
FLL
Fort Lauderdale - Hollywood Intl.
ISP
MacArthur
$273 Roundtrip, found 4 days ago
$273
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, May 13 from Fort Lauderdale - Hollywood Intl. to MacArthur, returning Sat, May 16, priced at $273 found 4 days ago
Delta
Mon, May 4 - Thu, May 7
CLE
Hopkins Intl.
HPN
Westchester County
$379 Roundtrip, found 8 hours ago
$379
Roundtrip
found 8 hours ago
Select Delta flight, departing Mon, May 4 from Hopkins Intl. to Westchester County, returning Thu, May 7, priced at $379 found 8 hours 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 $160, 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 $160 right now, why wait?

Westport Flight Information
Destination airport
MacArthur
Destination airport IATA code
ISP
Roundtrip price
$74

Last Minute Hotel Deals in Westport

Delamar Westport

Delamar Westport

4 out of 5
1595 Post Rd E Westport CT
Stay at this hotel in Westport. Enjoy free breakfast, free valet parking, and free train station pick-up. Popular attractions Southport Beach and Burying Hill ...
9.6/10 Exceptional! (63 reviews)
Wonderful hotel with a great bar/restaurant and wonderful and friendly staff.

Reviewed on Apr 25, 2026

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Delamar Westport
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
Book a stay at this business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.4/10 Very Good! (1,100 reviews)
Room was spotless. Plenty of space. Great parking. Friendly staff.

Reviewed on Apr 26, 2026

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EVEN Hotel Norwalk by IHG
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
Book a stay at this business-friendly hotel in Old Greenwich. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff ...
8.6/10 Excellent! (1,015 reviews)
I only used my cell phone. I didn't go to the bar. You must realize not everyone has a cell phone and can figure out how to access a QR code handed to them on a card at check in. I find this VERY!!!! frustrating. At check in, I think you should ask people if getting hotel info from that card is ok ...

Reviewed on Apr 28, 2026

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Hyatt Regency Greenwich
Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
111 Schoolhouse Road Milford CT
Book a stay at this business-friendly motel in Milford. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Hartford HealthCare Amphitheater ...
6.4/10 (1,008 reviews)
The hallway smelled like smoke, the elevator was broken

Reviewed on Apr 27, 2026

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Motel 6 Milford, CT
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! (1,749 reviews)
Very friendly workers , safe place to stay , walking distance to some places . U get what u pay for but it is actually a nice place . Would 100 percent stay there again if I’m back in that area .

Reviewed on Apr 27, 2026

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Amsterdam Hotel
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
Stay at this hotel in Trumbull. Enjoy an outdoor pool, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
8/10 Very Good! (1,000 reviews)
Great

Reviewed on Apr 28, 2026

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Trumbull Marriott Shelton
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 hotel in Stamford. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
6.8/10 (1,283 reviews)
I really like the people who work there. They always strived to help us and we felt well taken care of. Their breakfast in the morning was delicious......with so many choices ....... scrambled eggs, hard-boiled eggs, waffles, bagels, toast, muffins, fresh apples and oranges, and fresh hot coffee. ...

Reviewed on Apr 28, 2026

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La Quinta Inn & Suites by Wyndham Stamford / New York City
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
25 Old Stratford Rd Shelton CT
Book a stay at this business-friendly hotel in Shelton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8/10 Very Good! (1,119 reviews)
Everything was fine, except the coffee machine in the room did not work.

Reviewed on Apr 27, 2026

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Hilton Garden Inn Shelton
See all 1,109 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.