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Cheshire

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Cheshire Flights as Low as $146

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

Avelo Airlines
Mon, Jun 9 - Fri, Jun 13
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$146 Roundtrip, found 1 day ago
$146
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Mon, Jun 9 from Raleigh - Durham Intl. to Albany Intl., returning Fri, Jun 13, priced at $146 found 1 day ago
American Airlines
Mon, Jun 9 - Tue, Jun 10
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$187 Roundtrip, found 5 days ago
$187
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Jun 9 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Tue, Jun 10, priced at $187 found 5 days ago
Bargain Flight
Mon, Jun 9 - Fri, Jun 13
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Mon, Jun 9 from Raleigh - Durham Intl. to Albany Intl., returning Fri, Jun 13, priced at $198 found 1 day ago
Delta
Tue, Jun 3 - Tue, Jun 10
BUF
Buffalo Niagara Intl.
ALB
Albany Intl.
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 3 from Buffalo Niagara Intl. to Albany Intl., returning Tue, Jun 10, priced at $200 found 1 day ago
JetBlue Airways
Thu, Jun 12 - Mon, Jun 16
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$201 Roundtrip, found 5 days ago
$201
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Thu, Jun 12 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Mon, Jun 16, priced at $201 found 5 days ago
American Airlines
Wed, Jun 4 - Thu, Jun 5
BUF
Buffalo Niagara Intl.
ALB
Albany Intl.
$205 Roundtrip, found 11 hours ago
$205
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Jun 4 from Buffalo Niagara Intl. to Albany Intl., returning Thu, Jun 5, priced at $205 found 11 hours ago
JetBlue Airways
Fri, Jun 6 - Sun, Jun 8
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$207 Roundtrip, found 5 days ago
$207
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Fri, Jun 6 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Jun 8, priced at $207 found 5 days ago
Delta
Tue, Jun 3 - Thu, Jun 12
BUF
Buffalo Niagara Intl.
ALB
Albany Intl.
$208 Roundtrip, found 1 day ago
$208
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 3 from Buffalo Niagara Intl. to Albany Intl., returning Thu, Jun 12, priced at $208 found 1 day ago
American Airlines
Wed, Jun 4 - Thu, Jun 5
BUF
Buffalo Niagara Intl.
ALB
Albany Intl.
$214 Roundtrip, found 11 hours ago
$214
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Jun 4 from Buffalo Niagara Intl. to Albany Intl., returning Thu, Jun 5, priced at $214 found 11 hours ago
United
Wed, Jun 4 - Thu, Jun 5
BUF
Buffalo Niagara Intl.
ALB
Albany Intl.
$215 Roundtrip, found 11 hours ago
$215
Roundtrip
found 11 hours ago
Select United flight, departing Wed, Jun 4 from Buffalo Niagara Intl. to Albany Intl., returning Thu, Jun 5, priced at $215 found 11 hours ago
Breeze Airways
Sun, Jun 8 - Thu, Jun 12
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$234 Roundtrip, found 6 days ago
$234
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sun, Jun 8 from Raleigh - Durham Intl. to Albany Intl., returning Thu, Jun 12, priced at $234 found 6 days ago
American Airlines
Sat, Aug 9 - Sat, Aug 16
OMA
Eppley Field
ALB
Albany Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Aug 9 from Eppley Field to Albany Intl., returning Sat, Aug 16, priced at $237 found 1 day ago
Delta
Mon, Jul 7 - Fri, Jul 11
IAH
George Bush Intercontinental
ALB
Albany Intl.
$287 Roundtrip, found 6 days ago
$287
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Jul 7 from George Bush Intercontinental to Albany Intl., returning Fri, Jul 11, priced at $287 found 6 days ago
Delta
Tue, Jun 3 - Sat, Jun 7
ABQ
Albuquerque Intl. Sunport
ALB
Albany Intl.
$288 Roundtrip, found 1 day ago
$288
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 3 from Albuquerque Intl. Sunport to Albany Intl., returning Sat, Jun 7, priced at $288 found 1 day ago
American Airlines
Sat, Jul 5 - Fri, Jul 11
HOU
William P. Hobby
ALB
Albany Intl.
$507 Roundtrip, found 6 days ago
$507
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Jul 5 from William P. Hobby to Albany Intl., returning Fri, Jul 11, priced at $507 found 6 days ago
Alaska Airlines
Fri, Jun 6 - Sun, Jun 8
ABQ
Albuquerque Intl. Sunport
ALB
Albany Intl.
$1,073 Roundtrip, found 1 day ago
$1,073
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Fri, Jun 6 from Albuquerque Intl. Sunport to Albany Intl., returning Sun, Jun 8, priced at $1,073 found 1 day ago

Cheap Flights to Cheshire

Fall in love at first flight with your vacation to Cheshire 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 Cheshire on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Cheshire, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Cheshire

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Cheshire 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 ALB airport.

What is the cheapest month to fly to Cheshire?

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 Cheshire are in June, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Cheshire?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Cheshire.

What airport is best to fly into Cheshire?

When you’re planning your trip to Cheshire, convenience is the name of the game. Luckily, Cheshire Pittsfield Municipal Airport is nearby so you can deplane and get going on checking off everything on your Cheshire must-do list.

How much are flights to Cheshire?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Cheshire on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $146, 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 Cheshire?

The trick to saving a stack of cash on your flight to Cheshire? 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 $146 right now, why wait?

Last Minute Hotel Deals in Cheshire

Hotel Downstreet, Ascend Hotel Collection
Hotel Downstreet, Ascend Hotel Collection
3 out of 5
40 Main St, North Adams, MA
The price is $150 per night from May 19 to May 20
$150
includes taxes & fees
May 19 - May 20
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,000 reviews)
"Clean hotel but the price for the time of year was high in my opinion."

Reviewed on May 7, 2025

Hotel Downstreet, Ascend Hotel Collection
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is $149 per night from May 22 to May 23
$149
includes taxes & fees
May 22 - May 23
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (580 reviews)
"Really nice"

Reviewed on May 6, 2025

Life House Berkshires
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
The price is $123 per night from May 18 to May 19
$123
includes taxes & fees
May 18 - May 19
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
9/10 Wonderful! (1,000 reviews)
"Pleasant stay. Great staff. Really good Indian restaurant in the hotel. Peaceful and relaxing"

Reviewed on May 6, 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
The price is $113 per night from May 18 to May 19
$113
includes taxes & fees
May 18 - May 19
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,001 reviews)
"I had a wonderful stay at The Yankee, Trademark Collection by Wyndham. The room was beautiful and comfortable, making for a very relaxing experience. The staff was incredibly kind, welcoming, and made check-in and check-out effortless. However, during my visit, there was construction happening nearby, ..."

Reviewed on May 7, 2025

The Yankee, Trademark Collection by Wyndham
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
The price is $133 per night from May 11 to May 12
$133
includes taxes & fees
May 11 - May 12
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in ...
8.6/10 Excellent! (1,798 reviews)
"It was off season and quiet. Great price :)"

Reviewed on May 3, 2025

Vacation Village in the Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
The price is $144 per night from May 11 to May 12
$144
includes taxes & fees
May 11 - May 12
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (630 reviews)
"I enjoyed the place. Good staff and very helpful."

Reviewed on May 5, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Williams Inn
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
The price is $334 per night from May 11 to May 12
$334
includes taxes & fees
May 11 - May 12
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (448 reviews)
"."

Reviewed on May 1, 2025

The Williams Inn
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
The price is $211 per night from May 12 to May 13
$211
includes taxes & fees
May 12 - May 13
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,003 reviews)
"we stayed in the Stevens house. The driveway could use some attention."

Reviewed on Apr 30, 2025

The Red Lion Inn
See all 979 properties in Cheshire
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.