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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
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$164 Roundtrip, found 3 days ago
$164
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $164 found 3 days ago
Breeze Airways
Thu, Aug 7 - Sun, Aug 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$173 Roundtrip, found 5 days ago
$173
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Aug 7 from Orlando Intl. to Stewart Intl., returning Sun, Aug 10, priced at $173 found 5 days ago
Breeze Airways
Thu, Aug 7 - Sun, Aug 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$176 Roundtrip, found 5 days ago
$176
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Aug 7 from Orlando Intl. to Stewart Intl., returning Sun, Aug 10, priced at $176 found 5 days ago
Breeze Airways
Thu, Aug 7 - Sun, Aug 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$178 Roundtrip, found 5 days ago
$178
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Aug 7 from Orlando Intl. to Stewart Intl., returning Sun, Aug 10, priced at $178 found 5 days ago
Breeze Airways
Thu, Aug 7 - Sun, Aug 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$183 Roundtrip, found 5 days ago
$183
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Aug 7 from Orlando Intl. to Stewart Intl., returning Sun, Aug 10, priced at $183 found 5 days ago
Breeze Airways
Thu, Aug 7 - Sun, Aug 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$186 Roundtrip, found 5 days ago
$186
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Aug 7 from Orlando Intl. to Stewart Intl., returning Sun, Aug 10, priced at $186 found 5 days ago
Breeze Airways
Fri, Aug 15 - Sat, Aug 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$189 Roundtrip, found 5 hours ago
$189
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Orlando Intl. to Stewart Intl., returning Sat, Aug 23, priced at $189 found 5 hours ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$189 Roundtrip, found 6 hours ago
$189
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $189 found 6 hours ago
Breeze Airways
Fri, Aug 8 - Sun, Aug 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$192 Roundtrip, found 3 days ago
$192
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Aug 8 from Orlando Intl. to Stewart Intl., returning Sun, Aug 10, priced at $192 found 3 days ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$194 Roundtrip, found 6 hours ago
$194
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $194 found 6 hours ago
Breeze Airways
Fri, Aug 8 - Sun, Aug 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Aug 8 from Orlando Intl. to Stewart Intl., returning Sun, Aug 10, priced at $197 found 3 days ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$199 Roundtrip, found 5 days ago
$199
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $199 found 5 days ago
Breeze Airways
Fri, Aug 15 - Sat, Aug 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$199 Roundtrip, found 5 days ago
$199
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Aug 15 from Orlando Intl. to Stewart Intl., returning Sat, Aug 23, priced at $199 found 5 days ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$203 Roundtrip, found 5 days ago
$203
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $203 found 5 days ago
Breeze Airways
Fri, Aug 15 - Sat, Aug 23
MCO
Orlando Intl.
SWF
Stewart Intl.
$204 Roundtrip, found 5 days ago
$204
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Aug 15 from Orlando Intl. to Stewart Intl., returning Sat, Aug 23, priced at $204 found 5 days ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$208 Roundtrip, found 5 days ago
$208
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $208 found 5 days 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 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 $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
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! (1,000 reviews)
"Very clean and breakfast was worthy."

Reviewed on Jul 28, 2025

Get rates
Holiday Inn Express Hotel & Suites Chester by IHG
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd, Suffern, NY
Stay at this 3.5-star business-friendly hotel in Suffern. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,025 reviews)
"Beautiful hotel.. great ambiance .. good staff .. Would definitely recommend"

Reviewed on Jul 27, 2025

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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
Stay at this 3-star 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! (771 reviews)
"Place was great have stayed here many times."

Reviewed on Jul 30, 2025

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La Quinta Inn & Suites by Wyndham Middletown-Goshen
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 ...
8.2/10 Very Good! (1,017 reviews)
"Only complaints: No tea or coffee station, no breakfast included, fridge and dishwasher dated but other than that slept well, accessible to family and staff helpful."

Reviewed on Jul 29, 2025

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Sonesta Simply Suites Nanuet
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
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! (1,011 reviews)
"It’s very beautiful place.Gift shop it was amazing.My wife loved it and we bought bunch of gifts."

Reviewed on Jul 27, 2025

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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
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! (1,029 reviews)
"good friendly staff"

Reviewed on Jul 28, 2025

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Sleep Inn & Suites Middletown - Goshen
Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah

2.5 out of 5
290 Rt 17s, Mahwah, NJ
Book a stay at this business-friendly hotel in Mahwah. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,270 reviews)
"The bed was comfortable and the room was clean. Had everything we needed for one night. The building could use a little sprucing, but for an overnight stay, it is fine. Unfortunately, the breakfast was not good. Had many Hampton Inn breakfasts over the years and this one was seriously lacking. Coffee ..."

Reviewed on Jul 28, 2025

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Hampton Inn & Suites Mahwah
Super 8 by Wyndham Mahwah

Super 8 by Wyndham Mahwah

2.5 out of 5
160 State Route 17 South, Mahwah, NJ
Book a stay at this business-friendly hotel in Mahwah. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (1,007 reviews)
Pick the suite
"We reserved one of their family suites. It was so fun!"

Reviewed on Jul 26, 2025

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Super 8 by Wyndham Mahwah
See all 997 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.