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Westport

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Westport Flights as Low as $311

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

Delta
Wed, Feb 5 - Tue, Feb 18
ORD
O'Hare Intl.
HPN
Westchester County
$311 Roundtrip, found 17 hours ago
$311
Roundtrip
found 17 hours ago
Select Delta flight, departing Wed, Feb 5 from O'Hare Intl. to Westchester County, returning Tue, Feb 18, priced at $311 found 17 hours ago
Delta
Wed, Feb 5 - Tue, Feb 18
MDW
Midway Intl.
HPN
Westchester County
$311 Roundtrip, found 17 hours ago
$311
Roundtrip
found 17 hours ago
Select Delta flight, departing Wed, Feb 5 from Midway Intl. to Westchester County, returning Tue, Feb 18, priced at $311 found 17 hours ago
Delta
Mon, Feb 10 - Tue, Feb 18
MDW
Midway Intl.
HPN
Westchester County
$331 Roundtrip, found 17 hours ago
$331
Roundtrip
found 17 hours ago
Select Delta flight, departing Mon, Feb 10 from Midway Intl. to Westchester County, returning Tue, Feb 18, priced at $331 found 17 hours ago
Delta
Wed, Feb 5 - Wed, Feb 12
MDW
Midway Intl.
HPN
Westchester County
$333 Roundtrip, found 17 hours ago
$333
Roundtrip
found 17 hours ago
Select Delta flight, departing Wed, Feb 5 from Midway Intl. to Westchester County, returning Wed, Feb 12, priced at $333 found 17 hours ago
Delta
Sat, Feb 8 - Wed, Feb 12
MDW
Midway Intl.
HPN
Westchester County
$346 Roundtrip, found 17 hours ago
$346
Roundtrip
found 17 hours ago
Select Delta flight, departing Sat, Feb 8 from Midway Intl. to Westchester County, returning Wed, Feb 12, priced at $346 found 17 hours ago
Delta
Wed, Feb 5 - Fri, Feb 14
MDW
Midway Intl.
HPN
Westchester County
$348 Roundtrip, found 17 hours ago
$348
Roundtrip
found 17 hours ago
Select Delta flight, departing Wed, Feb 5 from Midway Intl. to Westchester County, returning Fri, Feb 14, priced at $348 found 17 hours ago
Delta
Thu, Feb 6 - Tue, Feb 18
ORD
O'Hare Intl.
HPN
Westchester County
$349 Roundtrip, found 17 hours ago
$349
Roundtrip
found 17 hours ago
Select Delta flight, departing Thu, Feb 6 from O'Hare Intl. to Westchester County, returning Tue, Feb 18, priced at $349 found 17 hours ago
Delta
Wed, Feb 5 - Sun, Feb 9
ORD
O'Hare Intl.
HPN
Westchester County
$353 Roundtrip, found 17 hours ago
$353
Roundtrip
found 17 hours ago
Select Delta flight, departing Wed, Feb 5 from O'Hare Intl. to Westchester County, returning Sun, Feb 9, priced at $353 found 17 hours ago
Delta
Sat, Feb 8 - Fri, Feb 14
MDW
Midway Intl.
HPN
Westchester County
$361 Roundtrip, found 17 hours ago
$361
Roundtrip
found 17 hours ago
Select Delta flight, departing Sat, Feb 8 from Midway Intl. to Westchester County, returning Fri, Feb 14, priced at $361 found 17 hours ago
Delta
Wed, Feb 5 - Mon, Feb 17
MDW
Midway Intl.
HPN
Westchester County
$362 Roundtrip, found 17 hours ago
$362
Roundtrip
found 17 hours ago
Select Delta flight, departing Wed, Feb 5 from Midway Intl. to Westchester County, returning Mon, Feb 17, priced at $362 found 17 hours ago
American Airlines
Sat, Feb 8 - Mon, Feb 10
ORD
O'Hare Intl.
HPN
Westchester County
$365 Roundtrip, found 17 hours ago
$365
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sat, Feb 8 from O'Hare Intl. to Westchester County, returning Mon, Feb 10, priced at $365 found 17 hours ago
American Airlines
Sun, Dec 29 - Mon, Jan 13
ATL
Hartsfield-Jackson Atlanta Intl.
HPN
Westchester County
$366 Roundtrip, found 3 hours ago
$366
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Sun, Dec 29 from Hartsfield-Jackson Atlanta Intl. to Westchester County, returning Mon, Jan 13, priced at $366 found 3 hours ago
Delta
Fri, Feb 7 - Fri, Feb 14
MDW
Midway Intl.
HPN
Westchester County
$368 Roundtrip, found 17 hours ago
$368
Roundtrip
found 17 hours ago
Select Delta flight, departing Fri, Feb 7 from Midway Intl. to Westchester County, returning Fri, Feb 14, priced at $368 found 17 hours ago
Delta
Wed, Feb 5 - Thu, Feb 13
MDW
Midway Intl.
HPN
Westchester County
$372 Roundtrip, found 17 hours ago
$372
Roundtrip
found 17 hours ago
Select Delta flight, departing Wed, Feb 5 from Midway Intl. to Westchester County, returning Thu, Feb 13, priced at $372 found 17 hours ago
Delta
Fri, Feb 7 - Sun, Feb 9
ORD
O'Hare Intl.
HPN
Westchester County
$373 Roundtrip, found 17 hours ago
$373
Roundtrip
found 17 hours ago
Select Delta flight, departing Fri, Feb 7 from O'Hare Intl. to Westchester County, returning Sun, Feb 9, priced at $373 found 17 hours ago
American Airlines
Sat, Feb 8 - Mon, Feb 10
ORD
O'Hare Intl.
HPN
Westchester County
$375 Roundtrip, found 17 hours ago
$375
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sat, Feb 8 from O'Hare Intl. to Westchester County, returning Mon, Feb 10, priced at $375 found 17 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 February, 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 $311, 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 $311 right now, why wait?

Westport Flight Information
Destination airport
Westchester County
Destination airport IATA code
HPN
Roundtrip price
$310

Last Minute Hotel Deals in Westport

Inn at Longshore
Inn at Longshore
2.5 out of 5
260 Compo Rd S, Westport, CT
The price is $183 per night from Dec 29 to Dec 30
$183
includes taxes & fees
Dec 29 - Dec 30
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! (131 reviews)
"Very clean and pleasant staff. Clean room. Affordable pricing"

Reviewed on Nov 24, 2024

Inn at Longshore
EVEN Hotel Norwalk, an IHG Hotel
EVEN Hotel Norwalk, an IHG Hotel
3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
The price is $111 per night from Jan 23 to Jan 24
$111
includes taxes & fees
Jan 23 - Jan 24, 2025
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 ...
8/10 Very Good! (1,007 reviews)
"Great stay"

Reviewed on Dec 15, 2024

EVEN Hotel Norwalk, an IHG Hotel
Amsterdam Hotel
Amsterdam Hotel
2 out of 5
19 Clarks Hill Ave, Stamford, CT
The price is $116 per night from Dec 25 to Dec 26
$116
includes taxes & fees
Dec 25 - Dec 26
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 ...
8.2/10 Very Good! (1,518 reviews)
"The hotel is in the downtown area conveniently located and within walking distance of the mall and restaurants. The staff was very friendly and helpful and the parking lot big and private. The hotel is old and in need of renovation but is clean and comfortable."

Reviewed on Dec 22, 2024

Amsterdam Hotel
Hyatt Regency Greenwich
Hyatt Regency Greenwich
4 out of 5
1800 E Putnam Avenue, Old Greenwich, CT
The price is $224 per night from Jan 10 to Jan 11
$224
includes taxes & fees
Jan 10 - Jan 11, 2025
Book a stay at this eco-certified hotel in Old Greenwich. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
7.6/10 Good! (1,004 reviews)
"The staff was AMAZING!"

Reviewed on Dec 21, 2024

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 $113 per night from Dec 29 to Dec 30
$113
includes taxes & fees
Dec 29 - Dec 30
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 ...
6/10 (282 reviews)
"Would recommend the hotel for a comfortable nights sleep"

Reviewed on Dec 20, 2024

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
The price is $116 per night from Dec 30 to Dec 31
$116
includes taxes & fees
Dec 30 - Dec 31
Stay at this 3-star business-friendly hotel in Shelton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
7.6/10 Good! (1,003 reviews)
"People are very kind the staff are very respectful they take care of us and the communication was very good."

Reviewed on Dec 21, 2024

Hilton Garden Inn Shelton
The Circle Hotel Fairfield
The Circle Hotel Fairfield
3 out of 5
417 Post Road, Fairfield, CT
The price is $160 per night from Jan 18 to Jan 19
$160
includes taxes & fees
Jan 18 - Jan 19, 2025
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! (1,261 reviews)
"We’ve stayed at this hotel several times and never been disappointed. Rooms are very clean, beds are comfortable. The only issue I had this time was, we asked for later check out (12:00) and housekeeping came knocking on our door and tried to enter at 9:30 am. 😕 They should know if people have checked ..."

Reviewed on Dec 21, 2024

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 $107 per night from Jan 3 to Jan 4
$107
includes taxes & fees
Jan 3 - Jan 4, 2025
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 ...
8.4/10 Very Good! (1,005 reviews)
"Super friendly staff and very easy check in."

Reviewed on Dec 22, 2024

Hyatt Place Milford / New Haven
See all 979 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.