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Chester

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Chester Flights as Low as $163

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 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 $163, 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 $163 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
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! (1,003 reviews)
The AC didn't work. It was a terrible night!

Reviewed on Apr 25, 2026

Holiday Inn Express Hotel & Suites Chester by IHG
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! (1,008 reviews)
Everything was great, smart TVs with app control would go long way 😀

Reviewed on Apr 26, 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! (1,107 reviews)
Large room at the very rear of the building overlooking the parking lot.

Reviewed on Apr 25, 2026

DoubleTree by Hilton Hotel Nanuet
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! (1,003 reviews)
I had reserved a room in the Lodge but without warning was shifted to the Summit Stone Cottage. Not very clean. The bathroom door hit the vanity so it would only open halfway. Had to sneak in sideways. Dumb installation. Not happy.

Reviewed on Apr 26, 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 ...
8/10 Very Good! (74 reviews)
The staff, especially Rosseanne, was the best. She was very friendly, attentive, and made sure that if we needed anything, we knew where to get it or who to get it from. Great property!

Reviewed on Apr 21, 2026

Spark by Hilton Fishkill
Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

2.5 out of 5
20 Overlook Blvd Nanuet NY
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 ...
8.4/10 Very Good! (1,181 reviews)
the room was nice and in good location. not much else outside the room to offer.

Reviewed on Apr 25, 2026

Sonesta Simply Suites Nanuet
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! (1,003 reviews)
Yes

Reviewed on Apr 23, 2026

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3 out of 5
24 Crystal Run Xing Middletown NY
Stay at this hotel in Middletown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
8.4/10 Very Good! (1,001 reviews)
Sufficient

Reviewed on Apr 25, 2026

Courtyard by Marriott Middletown Goshen
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.