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Chester

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Chester Flights as Low as $170

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

Breeze Airways
Wed, Sep 2 - Sat, Sep 5
TPA
Tampa Intl.
SWF
Stewart Intl.
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Sep 2 from Tampa Intl. to Stewart Intl., returning Sat, Sep 5, priced at $170 found 1 day ago
Breeze Airways
Wed, Sep 2 - Sat, Sep 5
TPA
Tampa Intl.
SWF
Stewart Intl.
$173 Roundtrip, found 1 day ago
$173
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Sep 2 from Tampa Intl. to Stewart Intl., returning Sat, Sep 5, priced at $173 found 1 day ago
Breeze Airways
Wed, Sep 2 - Sat, Sep 5
TPA
Tampa Intl.
SWF
Stewart Intl.
$175 Roundtrip, found 1 day ago
$175
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Sep 2 from Tampa Intl. to Stewart Intl., returning Sat, Sep 5, priced at $175 found 1 day ago
Breeze Airways
Wed, Sep 2 - Sat, Sep 5
TPA
Tampa Intl.
SWF
Stewart Intl.
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Sep 2 from Tampa Intl. to Stewart Intl., returning Sat, Sep 5, priced at $180 found 1 day ago
Breeze Airways
Wed, Sep 2 - Sat, Sep 5
TPA
Tampa Intl.
SWF
Stewart Intl.
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Sep 2 from Tampa Intl. to Stewart Intl., returning Sat, Sep 5, priced at $183 found 1 day ago
Breeze Airways
Tue, Sep 1 - Sat, Sep 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$193 Roundtrip, found 6 hours ago
$193
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando Intl. to Stewart Intl., returning Sat, Sep 5, priced at $193 found 6 hours ago
Breeze Airways
Tue, Sep 1 - Sat, Sep 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$198 Roundtrip, found 6 hours ago
$198
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando Intl. to Stewart Intl., returning Sat, Sep 5, priced at $198 found 6 hours ago
Breeze Airways
Sat, Jun 20 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$201 Roundtrip, found 6 days ago
$201
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sat, Jun 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $201 found 6 days ago
Breeze Airways
Tue, Sep 1 - Sat, Sep 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$203 Roundtrip, found 6 hours ago
$203
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando Intl. to Stewart Intl., returning Sat, Sep 5, priced at $203 found 6 hours ago
Breeze Airways
Sat, Jun 20 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$206 Roundtrip, found 5 days ago
$206
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Jun 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $206 found 5 days ago
Breeze Airways
Sat, Jun 20 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$212 Roundtrip, found 11 hours ago
$212
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Sat, Jun 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $212 found 11 hours ago
Breeze Airways
Sat, Aug 1 - Wed, Aug 5
TPA
Tampa Intl.
SWF
Stewart Intl.
$214 Roundtrip, found 18 hours ago
$214
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Sat, Aug 1 from Tampa Intl. to Stewart Intl., returning Wed, Aug 5, priced at $214 found 18 hours ago
Breeze Airways
Sat, Jun 20 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$217 Roundtrip, found 11 hours ago
$217
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Sat, Jun 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $217 found 11 hours ago
Breeze Airways
Sat, Aug 1 - Wed, Aug 5
TPA
Tampa Intl.
SWF
Stewart Intl.
$219 Roundtrip, found 18 hours ago
$219
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Sat, Aug 1 from Tampa Intl. to Stewart Intl., returning Wed, Aug 5, priced at $219 found 18 hours ago
Breeze Airways
Sat, Jun 20 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$222 Roundtrip, found 11 hours ago
$222
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Sat, Jun 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at $222 found 11 hours ago
Breeze Airways
Tue, Sep 1 - Sat, Sep 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$223 Roundtrip, found 6 hours ago
$223
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando Intl. to Stewart Intl., returning Sat, Sep 5, priced at $223 found 6 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 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 $170, 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 $170 right now, why wait?

Chester Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$170

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! (1,007 reviews)
"Many kids come to this hotel. Pool very nice. Fun things to do a walk away, legoland not far"

Reviewed on Jun 8, 2026

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Holiday Inn Express Hotel & Suites Chester by IHG
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! (124 reviews)
"This is clearly an older building and the carpets looked worn and shabby and hallway could use some paint. But it was very clean, the bed was surprisingly comfortable and the room had all the basics we needed. Breakfast was more limited than most. They served hardboiled eggs that were stone cold ..."

Reviewed on Jun 8, 2026

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Spark by Hilton Fishkill
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd Newburgh NY
Book a stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. ...
7/10 Good! (772 reviews)
"Staff was unavailable most of my stay during the evening hours from their front desk. Window blinds were absolutely disgusting and covered in dust and dead bugs. The rug and one chair in the room was covered in stains ranging from red blood like marks to brown stains. It felt disgusting to walk around ..."

Reviewed on Jun 7, 2026

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The Crossroads Hotel, Newburgh
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! (1,150 reviews)
"A huge hotel! The property was well maintained and clean. Some of the furniture and fixtures were obviously worn out - the headboard was worn out in spots, the refrigerator door did not close, the vanity had lots of scuff marks - but mattress and bedding were comfortable. The pool and gym were great. ..."

Reviewed on Jun 8, 2026

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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! (1,018 reviews)
"Staying at Bear Mountain Inn was amazing. Hessian Lake is beautiful. The park and trails are clean and hiking here is very good. We loved the Bear Mountain Zoo and all the exhibits. Staff here are very good. I highly recommend staying here. The rooms, decor, staff and ambiance are top notch. We will ..."

Reviewed on Jun 7, 2026

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Overlook Lodge at Bear Mountain
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! (1,222 reviews)
"Clean room, helpful and friendly staff"

Reviewed on Jun 7, 2026

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Sonesta Simply Suites Nanuet
Studio 6 Extended Stay Fishkill Route 9 NY

Studio 6 Extended Stay Fishkill Route 9 NY

2.5 out of 5
25 Merritt Blvd Fishkill NY
Stay at this hotel in Fishkill. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Van Wyck Homestead Museum and Fishkill Golf Course ...
6.6/10 (1,005 reviews)
"Kitchen was clean, the room was clean, the bathroom had two tiny soaps, one at the bathtub and one at the sink. More than enough towels. Encountered a couple of very big ants in the bathroom. The reception area was deplorable. The front two floor mats in front of the reception area were disgusting ..."

Reviewed on Jun 8, 2026

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Studio 6 Extended Stay Fishkill Route 9 NY
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 ...
8.8/10 Excellent! (1,008 reviews)
"No room service on day one of my vist as they had weddings everything else was nice breakfast fresh staff lovely"

Reviewed on Jun 1, 2026

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Crowne Plaza Suffern - Mahwah by IHG
See all 1,078 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.