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Chester

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Chester Flights as Low as $167

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

Breeze Airways
Fri, Jul 25 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$167 Roundtrip, found 4 days ago
$167
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jul 25 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $167 found 4 days ago
Breeze Airways
Fri, Jul 25 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$172 Roundtrip, found 4 days ago
$172
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jul 25 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $172 found 4 days ago
Breeze Airways
Thu, Jul 24 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$175 Roundtrip, found 3 days ago
$175
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jul 24 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $175 found 3 days ago
Breeze Airways
Fri, Jul 25 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$177 Roundtrip, found 4 days ago
$177
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jul 25 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $177 found 4 days ago
Breeze Airways
Fri, Aug 1 - Sun, Aug 3
MCO
Orlando Intl.
SWF
Stewart Intl.
$178 Roundtrip, found 4 days ago
$178
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Stewart Intl., returning Sun, Aug 3, priced at $178 found 4 days ago
Breeze Airways
Thu, Aug 14 - Sun, Aug 17
MCO
Orlando Intl.
SWF
Stewart Intl.
$180 Roundtrip, found 6 hours ago
$180
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Thu, Aug 14 from Orlando Intl. to Stewart Intl., returning Sun, Aug 17, priced at $180 found 6 hours ago
Breeze Airways
Thu, Jul 24 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$182 Roundtrip, found 20 hours ago
$182
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Thu, Jul 24 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $182 found 20 hours ago
Breeze Airways
Fri, Aug 1 - Sun, Aug 3
MCO
Orlando Intl.
SWF
Stewart Intl.
$183 Roundtrip, found 4 days ago
$183
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Stewart Intl., returning Sun, Aug 3, priced at $183 found 4 days ago
Breeze Airways
Fri, Aug 1 - Sun, Aug 3
MCO
Orlando Intl.
SWF
Stewart Intl.
$184 Roundtrip, found 4 days ago
$184
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Stewart Intl., returning Sun, Aug 3, priced at $184 found 4 days ago
Breeze Airways
Thu, Jul 24 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$185 Roundtrip, found 4 days ago
$185
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jul 24 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $185 found 4 days ago
Breeze Airways
Fri, Jul 25 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$186 Roundtrip, found 2 hours ago
$186
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Fri, Jul 25 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $186 found 2 hours ago
Breeze Airways
Thu, Jul 24 - Sun, Jul 27
MCO
Orlando Intl.
SWF
Stewart Intl.
$188 Roundtrip, found 5 hours ago
$188
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Thu, Jul 24 from Orlando Intl. to Stewart Intl., returning Sun, Jul 27, priced at $188 found 5 hours ago
Breeze Airways
Fri, Aug 15 - Mon, Aug 18
CHS
Charleston Intl.
SWF
Stewart Intl.
$190 Roundtrip, found 2 days ago
$190
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Aug 15 from Charleston Intl. to Stewart Intl., returning Mon, Aug 18, priced at $190 found 2 days ago
Fly Play
Sat, Jul 19 - Sun, Jul 20
KEF
Keflavik Intl.
SWF
Stewart Intl.
$371 Roundtrip, found 6 hours ago
$371
Roundtrip
found 6 hours ago
Select Fly Play flight, departing Sat, Jul 19 from Keflavik Intl. to Stewart Intl., returning Sun, Jul 20, priced at $371 found 6 hours ago
World Ticket Ltd
Sat, Jul 19 - Sun, Jul 20
KEF
Keflavik Intl.
SWF
Stewart Intl.
$582 Roundtrip, found 6 hours ago
$582
Roundtrip
found 6 hours ago
Select World Ticket Ltd flight, departing Sat, Jul 19 from Keflavik Intl. to Stewart Intl., returning Sun, Jul 20, priced at $582 found 6 hours ago
Fly Play
Sat, Jul 19 - Sat, Jul 26
CDG
Roissy-Charles de Gaulle
SWF
Stewart Intl.
$783 Roundtrip, found 2 days ago
$783
Roundtrip
found 2 days ago
Select Fly Play flight, departing Sat, Jul 19 from Roissy-Charles de Gaulle to Stewart Intl., returning Sat, Jul 26, priced at $783 found 2 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 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 $167, 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 $167 right now, why wait?

Chester Flight Information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Roundtrip price
$167

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! (1,005 reviews)
"It felt luxurious"

Reviewed on Jun 24, 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! (1,002 reviews)
Business Stay
"Overall the facility was very nice. Breakfast buffet and staff were excellent. The room was clean, but the AC was extremely loud and you could hear water dripping in pipes in the wall. Also, the TV remote was not working and the TV randomly came on at 2am."

Reviewed on Jul 9, 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! (743 reviews)
"Overall had a nice stay"

Reviewed on Jul 8, 2025

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La Quinta Inn & Suites by Wyndham 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! (1,008 reviews)
"Unique and quiet.safe for solo travelers and with companion."

Reviewed on Jul 7, 2025

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Overlook Lodge at Bear Mountain
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! (1,001 reviews)
"NA"

Reviewed on Jun 29, 2025

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Super 8 by Wyndham Mahwah
Hampton Inn Harriman Woodbury
Hampton Inn Harriman Woodbury
2.5 out of 5
60 Centre Dr, Central Valley, NY
Book a stay at this business-friendly hotel in Woodbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,008 reviews)
"Great room and experience overall"

Reviewed on Jul 6, 2025

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Hampton Inn Harriman Woodbury
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)
Worth the stay
"Excellent location right off the highway. Location also good for shopping and places to eat. Safe and quiet area and the cost was very reasonalable. The only drawback is on one side of the building is train tracks.Last time I was there, I did not know that.This time I asked for a room on the other ..."

Reviewed on Jul 7, 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! (1,000 reviews)
"It was very clean. Breakfast buffet was great"

Reviewed on Jun 28, 2025

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Best Western The Inn At Ramsey
See all 989 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.