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Westport

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Westport Flights as Low as $122

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

Breeze Airways
Wed, May 27 - Sat, Jun 6
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$122 Roundtrip, found 3 hours ago
$122
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Wed, May 27 from Raleigh - Durham Intl. to Westchester County, returning Sat, Jun 6, priced at $122 found 3 hours ago
Breeze Airways
Wed, May 27 - Sat, Jun 6
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$127 Roundtrip, found 3 hours ago
$127
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Wed, May 27 from Raleigh - Durham Intl. to Westchester County, returning Sat, Jun 6, priced at $127 found 3 hours ago
Breeze Airways
Wed, May 27 - Sat, Jun 6
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$132 Roundtrip, found 3 hours ago
$132
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Wed, May 27 from Raleigh - Durham Intl. to Westchester County, returning Sat, Jun 6, priced at $132 found 3 hours ago
Avelo Airlines
Mon, Apr 13 - Wed, Apr 22
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, Apr 22, priced at $138 found 1 day ago
Frontier Airlines
Sat, May 2 - Sun, May 3
ATL
Hartsfield-Jackson Atlanta Intl.
ISP
MacArthur
$140 Roundtrip, found 19 hours ago
$140
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, May 2 from Hartsfield-Jackson Atlanta Intl. to MacArthur, returning Sun, May 3, priced at $140 found 19 hours ago
Frontier Airlines
Sun, May 3 - Mon, May 4
ATL
Hartsfield-Jackson Atlanta Intl.
ISP
MacArthur
$153 Roundtrip, found 6 days ago
$153
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sun, May 3 from Hartsfield-Jackson Atlanta Intl. to MacArthur, returning Mon, May 4, priced at $153 found 6 days ago
Frontier Airlines
Sat, May 2 - Sun, May 3
ATL
Hartsfield-Jackson Atlanta Intl.
ISP
MacArthur
$160 Roundtrip, found 19 hours ago
$160
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, May 2 from Hartsfield-Jackson Atlanta Intl. to MacArthur, returning Sun, May 3, priced at $160 found 19 hours ago
Frontier Airlines
Wed, Apr 29 - Sun, May 3
ATL
Hartsfield-Jackson Atlanta Intl.
ISP
MacArthur
$162 Roundtrip, found 1 day ago
$162
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Apr 29 from Hartsfield-Jackson Atlanta Intl. to MacArthur, returning Sun, May 3, priced at $162 found 1 day ago
Avelo Airlines
Mon, Apr 13 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$164 Roundtrip, found 1 day ago
$164
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $164 found 1 day ago
Avelo Airlines
Mon, Apr 13 - Thu, Apr 23
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$172 Roundtrip, found 2 days ago
$172
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Thu, Apr 23, priced at $172 found 2 days ago
Frontier Airlines
Tue, May 5 - Sat, May 9
ATL
Hartsfield-Jackson Atlanta Intl.
ISP
MacArthur
$173 Roundtrip, found 6 days ago
$173
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, May 5 from Hartsfield-Jackson Atlanta Intl. to MacArthur, returning Sat, May 9, priced at $173 found 6 days ago
Breeze Airways
Sun, May 31 - Sat, Jun 13
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$176 Roundtrip, found 1 day ago
$176
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, May 31 from Raleigh - Durham Intl. to Westchester County, returning Sat, Jun 13, priced at $176 found 1 day ago
American Airlines
Wed, Apr 22 - Tue, Apr 28
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$211 Roundtrip, found 22 hours ago
$211
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Wed, Apr 22 from Raleigh - Durham Intl. to Westchester County, returning Tue, Apr 28, priced at $211 found 22 hours ago
Delta
Wed, May 27 - Sat, Jun 6
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$222 Roundtrip, found 3 hours ago
$222
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, May 27 from Raleigh - Durham Intl. to Westchester County, returning Sat, Jun 6, priced at $222 found 3 hours ago
Delta
Fri, Jun 5 - Tue, Jun 16
ATL
Hartsfield-Jackson Atlanta Intl.
HPN
Westchester County
$272 Roundtrip, found 4 hours ago
$272
Roundtrip
found 4 hours ago
Select Delta flight, departing Fri, Jun 5 from Hartsfield-Jackson Atlanta Intl. to Westchester County, returning Tue, Jun 16, priced at $272 found 4 hours ago
JetBlue Airways
Thu, May 7 - Wed, May 27
ATL
Hartsfield-Jackson Atlanta Intl.
HPN
Westchester County
$345 Roundtrip, found 1 day ago
$345
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, May 7 from Hartsfield-Jackson Atlanta Intl. to Westchester County, returning Wed, May 27, priced at $345 found 1 day 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 May, 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 $122, 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 $122 right now, why wait?

Westport Flight Information
Destination airport
MacArthur
Destination airport IATA code
ISP
Roundtrip price
$88

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! (46 reviews)
Beautiful Hotel! EVERYONE was kind, friendly and helpful. You have an amazing staff!!!! Exceeded my expectations. The Lobby smells wonderful !!! We will be back and will highly recommend your Hotel. Especially loved the wall with the woman in black dresses! ( You should make post cards and prints ...

Reviewed on Apr 6, 2026

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Delamar Westport
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 Silver Sands State Park ...
6.2/10 (1,001 reviews)
Buena ubicación

Reviewed on Apr 5, 2026

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Motel 6 Milford, CT
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane Milford CT
Book a stay at this 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! (1,291 reviews)
The breakfast is excellent. A lot of choices. The room is spacious and clean. The staff are nice.

Reviewed on Apr 6, 2026

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Hyatt Place Milford / New Haven
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! (1,002 reviews)
The room was eh at best… our mattress was coming apart, the sheets were too small for the mattress & didn’t fit, there were stains on the ill fitting bed skirts, there was no garbage pail in the room, only the bathroom, the wood flooring in the vanity area was water logged and sagging, the sink didn’t ...

Reviewed on Apr 7, 2026

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Trumbull Marriott Shelton
Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue Norwalk CT
Book a stay at this business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff ...
8.8/10 Excellent! (1,453 reviews)
Noisy. Can hear someone talking in other rooms

Reviewed on Apr 8, 2026

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Norwalk Inn & Conference Center
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 ...
8.4/10 Very Good! (1,002 reviews)
The room was very clean. There was very loud music in the middle of the night that seemed to come from the atrium but it eventually stopped so we were finally able to get some sleep. That was the only slightly bad thing we could say and it wasn't the hotels fault. Everything else was terrific.

Reviewed on Apr 8, 2026

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Hyatt Regency Greenwich
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 ...
Get rates
Amsterdam Hotel
Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
Book a stay at this business-friendly hotel in Bethel. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our ...
7.8/10 Good! (1,007 reviews)
Hotel was nice, breakfast was rather good, but bed was easy to hard for my liking.

Reviewed on Apr 6, 2026

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Best Western Danbury/Bethel
See all 1,106 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.