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Chester

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Chester Flights as Low as $112

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

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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 September, 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 $112, 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 $112 right now, why wait?

Chester Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$111

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
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 ...
8.6/10 Excellent! (1,001 reviews)
"Excellent breakfast. Very clean rooms. Bathrooms/shower needs to be updated."

Reviewed on Jun 30, 2026

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 NY
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 ...
8.4/10 Very Good! (1,009 reviews)
"Eh… understaffed, depressing. loud rooms (stone cottages) - could hear other rooms’ conversations and snoring and doors SLAMMING… as well as LOUD vehicles on adjacent road continuously.. we are learning where to stay for our kid at West Point …. This was trial 1 at a local “hotel”"

Reviewed on Jun 30, 2026

Overlook Lodge at Bear Mountain
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Book a stay at this golf hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
8.2/10 Very Good! (148 reviews)
"No cups in the room. Ants in the breakfast area."

Reviewed on Jun 30, 2026

Spark by Hilton Fishkill
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
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 ...
8.8/10 Excellent! (1,046 reviews)
"Rooms were clean. Pool was great. Breakfast was nice variety. Only thing there was bridal or wedding party going on all night across the hall way. People were very loud and disrespectful. Even staff had to warn them several times. That was only frustrating part, I couldn’t truly enjoy my stay with ..."

Reviewed on Jul 1, 2026

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
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. ...
9/10 Wonderful! (1,160 reviews)
"Parfait"

Reviewed on Jun 28, 2026

DoubleTree by Hilton Hotel Nanuet
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd Suffern NY
Book a stay at this business-friendly hotel in Suffern. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,000 reviews)
"The hotel was updated and clean and perfect to accompany a small dog. They can have more electric chargers."

Reviewed on Jun 30, 2026

Crowne Plaza Suffern - Mahwah by IHG
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
551 Route 211 E Middletown NY
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 ...
9.4/10 Exceptional! (1,007 reviews)
"My family and I had a wonderful stay here! It was conveniently located close to LEGOLAND, which made our trip so much easier. The boys absolutely loved the pool, and the complimentary breakfast was surprisingly phenomenal with plenty of great options. The gym was perfect for me to do a bit of strength ..."

Reviewed on Jun 30, 2026

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Days Inn by Wyndham Nanuet / Spring Valley

Days Inn by Wyndham Nanuet / Spring Valley

2 out of 5
367 W Route 59 Nanuet NY
Book a stay at this business-friendly motel in Nanuet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
7/10 Good! (1,004 reviews)
"Friendly staff. Clean room."

Reviewed on Jun 28, 2026

Days Inn by Wyndham Nanuet / Spring Valley
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.