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Chester

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Chester Flights as Low as $140

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

Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$140 Roundtrip, found 5 days ago
$140
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $140 found 5 days ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$143 Roundtrip, found 3 days ago
$143
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $143 found 3 days ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$145 Roundtrip, found 5 days ago
$145
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $145 found 5 days ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$146 Roundtrip, found 3 days ago
$146
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $146 found 3 days ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$150 Roundtrip, found 5 days ago
$150
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $150 found 5 days ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$153 Roundtrip, found 3 days ago
$153
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $153 found 3 days ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$155 Roundtrip, found 5 days ago
$155
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $155 found 5 days ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$156 Roundtrip, found 2 days ago
$156
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $156 found 2 days ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $157 found 1 day ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$160 Roundtrip, found 5 days ago
$160
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $160 found 5 days ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$161 Roundtrip, found 20 hours ago
$161
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $161 found 20 hours ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$162 Roundtrip, found 11 hours ago
$162
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $162 found 11 hours ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$165 Roundtrip, found 5 days ago
$165
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $165 found 5 days ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$166 Roundtrip, found 20 hours ago
$166
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $166 found 20 hours ago
Breeze Airways
Fri, Apr 25 - Mon, Apr 28
CHS
Charleston Intl.
SWF
Stewart Intl.
$168 Roundtrip, found 11 hours ago
$168
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Fri, Apr 25 from Charleston Intl. to Stewart Intl., returning Mon, Apr 28, priced at $168 found 11 hours ago
Breeze Airways
Thu, Jul 17 - Sun, Jul 20
ROC
Greater Rochester Intl.
SWF
Stewart Intl.
$583 Roundtrip, found 12 hours ago
$583
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Thu, Jul 17 from Greater Rochester Intl. to Stewart Intl., returning Sun, Jul 20, priced at $583 found 12 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 May, 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 $140, 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 $140 right now, why wait?

Chester Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$139

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 $166 per night from Apr 20 to Apr 21
$166
includes taxes & fees
Apr 20 - Apr 21
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! (1,002 reviews)
"I only stayed for the night but the front desk was nice and quick. Area is very quiet and peaceful."

Reviewed on Apr 11, 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 $135 per night from Apr 20 to Apr 21
$135
includes taxes & fees
Apr 20 - Apr 21
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! (1,000 reviews)
"Very friendly staff. Rooms are clean."

Reviewed on Apr 12, 2025

Overlook Lodge at Bear Mountain
Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - Goshen
2.5 out of 5
3491 Route 6, Middletown, NY
The price is $152 per night from Apr 30 to May 1
$152
includes taxes & fees
Apr 30 - May 1
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! (1,010 reviews)
"Room was clean, quiet property"

Reviewed on Apr 12, 2025

Sleep Inn & Suites Middletown - Goshen
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 $153 per night from Apr 27 to Apr 28
$153
includes taxes & fees
Apr 27 - Apr 28
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! (669 reviews)
"Clean place easy check in and out no issues"

Reviewed on Apr 10, 2025

La Quinta Inn & Suites by Wyndham Middletown
DoubleTree by Hilton Hotel Nanuet
DoubleTree by Hilton Hotel Nanuet
4 out of 5
425 E Route 59, Nanuet, NY
The price is $138 per night from Apr 27 to Apr 28
$138
includes taxes & fees
Apr 27 - Apr 28
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! (1,002 reviews)
"after a long trip it was very welcoming and comfortable. The staff was wonderful"

Reviewed on Apr 1, 2025

DoubleTree by Hilton Hotel Nanuet
Sonesta Simply Suites Nanuet
Sonesta Simply Suites Nanuet
2.5 out of 5
20 Overlook Blvd, Nanuet, NY
The price is $119 per night from May 11 to May 12
$119
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! (1,005 reviews)
"I"

Reviewed on Apr 12, 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 $133 per night from Apr 27 to Apr 28
$133
includes taxes & fees
Apr 27 - Apr 28
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! (1,005 reviews)
Great stay
"Renovated n looks bright n clean"

Reviewed on Apr 11, 2025

Hampton Inn Harriman Woodbury
Extended Stay America Suites Ramsey Upper Saddle River
Extended Stay America Suites Ramsey Upper Saddle River
2.5 out of 5
112 State Hwy. 17, Ramsey, NJ
The price is $121 per night from May 3 to May 4
$121
includes taxes & fees
May 3 - May 4
Book a stay at this business-friendly hotel in Ramsey. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
6.6/10 (920 reviews)
"Amazing"

Reviewed on Apr 7, 2025

Extended Stay America Suites Ramsey Upper Saddle River
See all 988 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.