Search Cheap Flights to
Ossining

Photo by Linda Zanetti

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Ossining Flights as Low as $165

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

Breeze Airways
Thu, Jun 12 - Mon, Jun 16
CHS
Charleston Intl.
HPN
Westchester County
$165 Roundtrip, found 5 days ago
$165
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jun 12 from Charleston Intl. to Westchester County, returning Mon, Jun 16, priced at $165 found 5 days ago
Delta
Sat, Jun 7 - Mon, Jun 9
RSW
Southwest Florida Intl.
LGA
LaGuardia
$167 Roundtrip, found 3 days ago
$167
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Jun 7 from Southwest Florida Intl. to LaGuardia, returning Mon, Jun 9, priced at $167 found 3 days ago
Spirit Airlines
Tue, May 6 - Wed, May 7
CHS
Charleston Intl.
LGA
LaGuardia
$169 Roundtrip, found 13 hours ago
$169
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Tue, May 6 from Charleston Intl. to LaGuardia, returning Wed, May 7, priced at $169 found 13 hours ago
Delta
Wed, Jun 4 - Mon, Jun 9
RSW
Southwest Florida Intl.
LGA
LaGuardia
$170 Roundtrip, found 3 days ago
$170
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jun 4 from Southwest Florida Intl. to LaGuardia, returning Mon, Jun 9, priced at $170 found 3 days ago
Breeze Airways
Thu, Jun 12 - Mon, Jun 16
CHS
Charleston Intl.
HPN
Westchester County
$176 Roundtrip, found 5 days ago
$176
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jun 12 from Charleston Intl. to Westchester County, returning Mon, Jun 16, priced at $176 found 5 days ago
Delta
Sat, Jun 7 - Sun, Jun 8
RSW
Southwest Florida Intl.
LGA
LaGuardia
$177 Roundtrip, found 3 days ago
$177
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Jun 7 from Southwest Florida Intl. to LaGuardia, returning Sun, Jun 8, priced at $177 found 3 days ago
Delta
Thu, May 29 - Fri, May 30
RSW
Southwest Florida Intl.
LGA
LaGuardia
$179 Roundtrip, found 4 days ago
$179
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, May 29 from Southwest Florida Intl. to LaGuardia, returning Fri, May 30, priced at $179 found 4 days ago
Delta
Sun, Jun 8 - Wed, Jun 11
RSW
Southwest Florida Intl.
LGA
LaGuardia
$181 Roundtrip, found 3 days ago
$181
Roundtrip
found 3 days ago
Select Delta flight, departing Sun, Jun 8 from Southwest Florida Intl. to LaGuardia, returning Wed, Jun 11, priced at $181 found 3 days ago
Delta
Wed, May 28 - Thu, May 29
RSW
Southwest Florida Intl.
LGA
LaGuardia
$183 Roundtrip, found 4 days ago
$183
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, May 28 from Southwest Florida Intl. to LaGuardia, returning Thu, May 29, priced at $183 found 4 days ago
Bargain Flight
Wed, May 14 - Mon, May 19
CHS
Charleston Intl.
LGA
LaGuardia
$190 Roundtrip, found 5 days ago
$190
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Wed, May 14 from Charleston Intl. to LaGuardia, returning Mon, May 19, priced at $190 found 5 days ago
JetBlue Airways
Mon, Jun 9 - Sat, Jun 14
RSW
Southwest Florida Intl.
HPN
Westchester County
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Jun 9 from Southwest Florida Intl. to Westchester County, returning Sat, Jun 14, priced at $197 found 1 day ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$209 Roundtrip, found 11 hours ago
$209
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $209 found 11 hours ago
American Airlines
Wed, May 14 - Mon, May 19
CHS
Charleston Intl.
LGA
LaGuardia
$257 Roundtrip, found 5 days ago
$257
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, May 14 from Charleston Intl. to LaGuardia, returning Mon, May 19, priced at $257 found 5 days ago
American Airlines
Tue, Jun 3 - Tue, Jun 3
SEA
Seattle - Tacoma Intl.
LGA
LaGuardia
$261 Roundtrip, found 8 hours ago
$261
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Tue, Jun 3 from Seattle - Tacoma Intl. to LaGuardia, returning Tue, Jun 3, priced at $261 found 8 hours ago
American Airlines
Wed, May 21 - Fri, May 30
SEA
Seattle - Tacoma Intl.
HPN
Westchester County
$307 Roundtrip, found 10 hours ago
$307
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Wed, May 21 from Seattle - Tacoma Intl. to Westchester County, returning Fri, May 30, priced at $307 found 10 hours ago
Alaska Airlines
Wed, May 21 - Sat, May 31
SEA
Seattle - Tacoma Intl.
HPN
Westchester County
$424 Roundtrip, found 10 hours ago
$424
Roundtrip
found 10 hours ago
Select Alaska Airlines flight, departing Wed, May 21 from Seattle - Tacoma Intl. to Westchester County, returning Sat, May 31, priced at $424 found 10 hours ago

Cheap Flights to Ossining

Fall in love at first flight with your vacation to Ossining 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 Ossining on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Ossining, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Ossining

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Ossining 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 LGA airport.

What is the cheapest month to fly to Ossining?

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 Ossining are in June, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Ossining?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Ossining.

What airport is best to fly into Ossining?

When you’re planning your trip to Ossining, convenience is the name of the game. Luckily, Ossining Westchester County Airport is nearby so you can deplane and get going on checking off everything on your Ossining must-do list.

How much are flights to Ossining?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Ossining on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $165, 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 Ossining?

The trick to saving a stack of cash on your flight to Ossining? 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 $165 right now, why wait?

Ossining Flight Information
Destination airport
LaGuardia
Destination airport IATA code
LGA
Roundtrip price
$77

Last Minute Hotel Deals in Ossining

Hampton Inn & Suites Yonkers
Hampton Inn & Suites Yonkers
2.5 out of 5
160 Corporate Blvd, Yonkers, NY
The price is $149 per night from May 4 to May 5
$149
includes taxes & fees
May 4 - May 5
Book a stay at this business-friendly hotel in Yonkers. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,380 reviews)
"Over all the place was great and convenient."

Reviewed on Apr 28, 2025

Hampton Inn & Suites Yonkers
Amsterdam Hotel
Amsterdam Hotel
2 out of 5
19 Clarks Hill Ave, Stamford, CT
The price is $116 per night from May 4 to May 5
$116
includes taxes & fees
May 4 - May 5
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! (1,591 reviews)
"I like the quietness of the property and my dislike was not having a pool."

Reviewed on Apr 26, 2025

Amsterdam Hotel
Hyatt Regency Greenwich
Hyatt Regency Greenwich
4 out of 5
1800 E Putnam Avenue, Old Greenwich, CT
The price is $201 per night from May 25 to May 26
$201
includes taxes & fees
May 25 - May 26
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! (871 reviews)
"Since last visiting in 2022, the property has been updated and is quite nice for the price of the rooms. You get so much for what you are paying and the staff is delightful."

Reviewed on Apr 28, 2025

Hyatt Regency Greenwich
Royal Regency Hotel
Royal Regency Hotel
3.5 out of 5
165 Tuckahoe Rd, Yonkers, NY
The price is $138 per night from Jun 1 to Jun 2
$138
includes taxes & fees
Jun 1 - Jun 2
Book a stay at this business-friendly hotel in Yonkers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant ...
8.2/10 Very Good! (2,077 reviews)
"The breakfast was good and the staff were very nice. When I put out the DND sign, they still followed up with me later to make sure I didn't need anything. Great service!"

Reviewed on Apr 24, 2025

Royal Regency Hotel
Ramada by Wyndham Bronx
Ramada by Wyndham Bronx
3 out of 5
1000 Baychester Ave, Bronx, NY
The price is $144 per night from May 4 to May 5
$144
includes taxes & fees
May 4 - May 5
Stay at this 3-star business-friendly hotel in Bronx. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (1,002 reviews)
"small space. Toilet is very low. Really clean"

Reviewed on Apr 29, 2025

Ramada by Wyndham Bronx
Sonesta White Plains Downtown
Sonesta White Plains Downtown
4 out of 5
66 Hale Ave, White Plains, NY
The price is $219 per night from May 26 to May 27
$219
includes taxes & fees
May 26 - May 27
Book a stay at this business-friendly hotel in White Plains. Enjoy breakfast (surcharge), free airport pick-up, and room service. Our guests praise the bar and ...
8.6/10 Excellent! (1,111 reviews)
My Fave Hotel in White Plains
"From check-in to check-out, I was very pleased with my entire experience, and would recommend the Sonesta White Plains to anyone visiting this very nice and quaint city. The overall ambience of the entrance, lobby bar, restaurant, and pool, were clean, contemporary, and classy. My room was perfect ..."

Reviewed on Apr 29, 2025

Sonesta White Plains Downtown
Overlook Lodge at Bear Mountain
Overlook Lodge at Bear Mountain
2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
The price is $141 per night from May 4 to May 5
$141
includes taxes & fees
May 4 - May 5
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (1,001 reviews)
"The staff, room and property were lovely. The view from the porch? Spectacular !!!"

Reviewed on Apr 28, 2025

Overlook Lodge at Bear Mountain
Hilltop Inn & Suites
Hilltop Inn & Suites
2.5 out of 5
125 Tuckahoe Rd, Yonkers, NY
The price is $127 per night from May 4 to May 5
$127
includes taxes & fees
May 4 - May 5
Book a stay at this business-friendly hotel in Yonkers. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Westchester's Ridge Hill and ...
7/10 Good! (111 reviews)
"I enjoyed my stay."

Reviewed on Apr 27, 2025

Hilltop Inn & Suites
See all 1,165 properties in Ossining
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.