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Chester

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Chester Flights as Low as $212

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

Breeze Airways
Thu, Jul 3 - Sun, Jul 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$212 Roundtrip, found 2 days ago
$212
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jul 3 from Orlando Intl. to Stewart Intl., returning Sun, Jul 6, priced at $212 found 2 days ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$217 Roundtrip, found 3 hours ago
$217
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $217 found 3 hours ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$222 Roundtrip, found 1 day ago
$222
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $222 found 1 day ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$222 Roundtrip, found 3 hours ago
$222
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $222 found 3 hours ago
Breeze Airways
Thu, Jul 3 - Sun, Jul 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$224 Roundtrip, found 5 days ago
$224
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jul 3 from Orlando Intl. to Stewart Intl., returning Sun, Jul 6, priced at $224 found 5 days ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$227 Roundtrip, found 1 day ago
$227
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $227 found 1 day ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$227 Roundtrip, found 3 hours ago
$227
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $227 found 3 hours ago
Breeze Airways
Thu, Jul 3 - Sun, Jul 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$229 Roundtrip, found 2 days ago
$229
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Jul 3 from Orlando Intl. to Stewart Intl., returning Sun, Jul 6, priced at $229 found 2 days ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$232 Roundtrip, found 1 day ago
$232
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $232 found 1 day ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$233 Roundtrip, found 3 days ago
$233
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 $233 found 3 days ago
Breeze Airways
Thu, Jul 3 - Sun, Jul 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$234 Roundtrip, found 5 days ago
$234
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jul 3 from Orlando Intl. to Stewart Intl., returning Sun, Jul 6, priced at $234 found 5 days ago
Breeze Airways
Thu, Jul 3 - Sun, Jul 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$235 Roundtrip, found 1 day ago
$235
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Jul 3 from Orlando Intl. to Stewart Intl., returning Sun, Jul 6, priced at $235 found 1 day ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$238 Roundtrip, found 3 days ago
$238
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 $238 found 3 days ago
Breeze Airways
Thu, Sep 25 - Sun, Sep 28
MCO
Orlando Intl.
SWF
Stewart Intl.
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Sep 25 from Orlando Intl. to Stewart Intl., returning Sun, Sep 28, priced at $239 found 1 day ago
Breeze Airways
Thu, Oct 2 - Mon, Oct 6
CVG
Cincinnati - Northern Kentucky Intl.
SWF
Stewart Intl.
$468 Roundtrip, found 1 day ago
$468
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Oct 2 from Cincinnati - Northern Kentucky Intl. to Stewart Intl., returning Mon, Oct 6, priced at $468 found 1 day ago
Fly Play
Fri, Jun 20 - Tue, Jun 24
STN
Stansted
SWF
Stewart Intl.
$835 Roundtrip, found 1 day ago
$835
Roundtrip
found 1 day ago
Select Fly Play flight, departing Fri, Jun 20 from Stansted to Stewart Intl., returning Tue, Jun 24, priced at $835 found 1 day 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 July, 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 $212, 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 $212 right now, why wait?

Chester Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$212

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! (1,002 reviews)
Okay stay.
"It was an okay stay. The was a time where my keycards stopped working before we left. The breakfast was good but the first morning, there were some front desk employees kind of holding up a line in getting their breakfast before customers could get theirs. And the biscuits were not cooked all the ..."

Reviewed on Jun 16, 2025

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Holiday Inn Express Hotel & Suites Chester by IHG
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,016 reviews)
"Hotel was good, fairly clean. Older property. Simple room with plenty of space for 2 people."

Reviewed on Jun 15, 2025

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HYATT house Fishkill/Poughkeepsie
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
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 (976 reviews)
"This extended stay in New Jersey had construction on either side, so there was a lot of construction noise and I think most of the clients are people coming in for work to New Jersey or in and out of there we were there as a pitstop on the way to some somewhere else. It is a very basic room there’s ..."

Reviewed on Jun 14, 2025

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Extended Stay America Suites Ramsey Upper Saddle River
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! (1,006 reviews)
"The room and it's amenities were very well received and appreciated A very nice place to spend a few nights."

Reviewed on Jun 14, 2025

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Sonesta Simply Suites Nanuet
Best Western The Inn At Ramsey
Best Western The Inn At Ramsey
3 out of 5
1315 Route 17 South, Ramsey, NJ
Stay at this 3-star business-friendly hotel in Ramsey. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7.2/10 Good! (1,003 reviews)
"N/A"

Reviewed on Jun 14, 2025

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Best Western The Inn At Ramsey
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! (1,005 reviews)
"Friendly staff"

Reviewed on Jun 16, 2025

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Sleep Inn & Suites Middletown - Goshen
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! (1,001 reviews)
"Nice, great location"

Reviewed on Jun 16, 2025

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Overlook Lodge at Bear Mountain
Wingate by Wyndham Fishkill
Wingate by Wyndham Fishkill
3 out of 5
20 Schuyler Blvd, Fishkill, NY
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.6/10 Good! (414 reviews)
"A"

Reviewed on Jun 15, 2025

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Wingate by Wyndham Fishkill
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.