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Chester

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Chester Flights as Low as $164

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

Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 2 days ago
$164
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $164 found 2 days ago
Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $169 found 2 days ago
Breeze Airways
Sun, Jun 15 - Thu, Jun 19
MCO
Orlando Intl.
SWF
Stewart Intl.
$174 Roundtrip, found 2 days ago
$174
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Jun 15 from Orlando Intl. to Stewart Intl., returning Thu, Jun 19, priced at $174 found 2 days ago
Breeze Airways
Fri, Jun 6 - Mon, Jun 9
MCO
Orlando Intl.
SWF
Stewart Intl.
$195 Roundtrip, found 1 day ago
$195
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jun 6 from Orlando Intl. to Stewart Intl., returning Mon, Jun 9, priced at $195 found 1 day ago
Breeze Airways
Fri, Jun 6 - Mon, Jun 9
MCO
Orlando Intl.
SWF
Stewart Intl.
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jun 6 from Orlando Intl. to Stewart Intl., returning Mon, Jun 9, priced at $200 found 1 day ago
Breeze Airways
Fri, Jun 6 - Mon, Jun 9
MCO
Orlando Intl.
SWF
Stewart Intl.
$205 Roundtrip, found 1 day ago
$205
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jun 6 from Orlando Intl. to Stewart Intl., returning Mon, Jun 9, priced at $205 found 1 day ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$209 Roundtrip, found 15 hours ago
$209
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $209 found 15 hours ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$214 Roundtrip, found 15 hours ago
$214
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $214 found 15 hours ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$219 Roundtrip, found 15 hours ago
$219
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $219 found 15 hours ago
Breeze Airways
Thu, Jun 19 - Mon, Jun 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$225 Roundtrip, found 3 days ago
$225
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jun 19 from Orlando Intl. to Stewart Intl., returning Mon, Jun 23, priced at $225 found 3 days ago
Breeze Airways
Fri, Jun 20 - Tue, Jun 24
MCO
Orlando Intl.
SWF
Stewart Intl.
$230 Roundtrip, found 3 days ago
$230
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Jun 20 from Orlando Intl. to Stewart Intl., returning Tue, Jun 24, priced at $230 found 3 days ago
Breeze Airways
Thu, Jun 26 - Sun, Jun 29
MCO
Orlando Intl.
SWF
Stewart Intl.
$231 Roundtrip, found 2 days ago
$231
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jun 26 from Orlando Intl. to Stewart Intl., returning Sun, Jun 29, priced at $231 found 2 days ago
Breeze Airways
Thu, Jun 19 - Mon, Jun 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$235 Roundtrip, found 3 days ago
$235
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jun 19 from Orlando Intl. to Stewart Intl., returning Mon, Jun 23, priced at $235 found 3 days ago
Breeze Airways
Fri, Jun 20 - Tue, Jun 24
MCO
Orlando Intl.
SWF
Stewart Intl.
$240 Roundtrip, found 3 days ago
$240
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Jun 20 from Orlando Intl. to Stewart Intl., returning Tue, Jun 24, priced at $240 found 3 days ago
Breeze Airways
Thu, Jun 26 - Sun, Jun 29
MCO
Orlando Intl.
SWF
Stewart Intl.
$241 Roundtrip, found 2 days ago
$241
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jun 26 from Orlando Intl. to Stewart Intl., returning Sun, Jun 29, priced at $241 found 2 days ago
Breeze Airways
Thu, May 15 - Mon, May 19
CVG
Cincinnati - Northern Kentucky Intl.
SWF
Stewart Intl.
$524 Roundtrip, found 11 hours ago
$524
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Thu, May 15 from Cincinnati - Northern Kentucky Intl. to Stewart Intl., returning Mon, May 19, priced at $524 found 11 hours ago

Cheap Flights to Chester

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

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

Frequently Asked Questions About flights to Chester

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

What is the cheapest month to fly to Chester?

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

How many airlines fly to Chester?

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 Chester.

What airport is best to fly into Chester?

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

How much are flights to Chester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $164, 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 Chester?

The trick to saving a stack of cash on your flight to Chester? 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 $164 right now, why wait?

Chester Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$163

Last Minute Hotel Deals in Chester

Holiday Inn Express Hotel & Suites Chester by IHG
Holiday Inn Express Hotel & Suites Chester by IHG
2.5 out of 5
2 Bryle Place, Chester, NY
The price is $122 per night from May 4 to May 5
$122
includes taxes & fees
May 4 - May 5
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,001 reviews)
"Room is big and clean, bed is comfortable. About a 5-min drive away from Legoland. Would definitely stay here again if given the opportunity."

Reviewed on Apr 29, 2025

Holiday Inn Express Hotel & Suites Chester by IHG
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
La Quinta Inn & Suites by Wyndham Middletown
La Quinta Inn & Suites by Wyndham Middletown
2.5 out of 5
551 Route 211 E, Middletown, NY
The price is $150 per night from May 6 to May 7
$150
includes taxes & fees
May 6 - May 7
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (685 reviews)
Clean, friendly service, lots of parking
"Just an overnight stop but this place was perfect! It was quiet, clean, Elora at the front desk was lovely and it was reasonably priced."

Reviewed on Apr 28, 2025

La Quinta Inn & Suites by Wyndham Middletown
Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - Goshen
2.5 out of 5
3491 Route 6, Middletown, NY
The price is $134 per night from May 26 to May 27
$134
includes taxes & fees
May 26 - May 27
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,000 reviews)
"Great property close to legoland. We saw some ants coming out from an outlet into our room on the second day. We quickly made sure to put our food items in the fridge."

Reviewed on Apr 28, 2025

Sleep Inn & Suites Middletown - Goshen
DoubleTree by Hilton Hotel Nanuet
DoubleTree by Hilton Hotel Nanuet
4 out of 5
425 E Route 59, Nanuet, NY
The price is $133 per night from May 26 to May 27
$133
includes taxes & fees
May 26 - May 27
Book a stay at this golf hotel in Nanuet. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (1,000 reviews)
"Will recommand!"

Reviewed on Apr 27, 2025

DoubleTree by Hilton Hotel Nanuet
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
The price is $124 per night from May 11 to May 12
$124
includes taxes & fees
May 11 - May 12
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,000 reviews)
"Super clean"

Reviewed on Apr 28, 2025

HYATT house Fishkill/Poughkeepsie
Sonesta Simply Suites Nanuet
Sonesta Simply Suites Nanuet
2.5 out of 5
20 Overlook Blvd, Nanuet, NY
The price is $126 per night from May 11 to May 12
$126
includes taxes & fees
May 11 - May 12
Book a stay at this business-friendly hotel in Nanuet. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,004 reviews)
"Clean, quiet and comfortable with a well-appointed room and convenient location."

Reviewed on Apr 29, 2025

Sonesta Simply Suites Nanuet
Hampton Inn Harriman Woodbury
Hampton Inn Harriman Woodbury
2.5 out of 5
60 Centre Dr, Central Valley, NY
The price is $161 per night from May 4 to May 5
$161
includes taxes & fees
May 4 - May 5
Book a stay at this business-friendly hotel in Woodbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,001 reviews)
"Clean, comfortable. Good value."

Reviewed on Apr 27, 2025

Hampton Inn Harriman Woodbury
See all 977 properties in Chester
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.