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Cheshire

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Cheshire Flights as Low as $221

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

American Airlines
Fri, Jun 6 - Wed, Jun 11
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$221 Roundtrip, found 11 hours ago
$221
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Fri, Jun 6 from Dallas-Fort Worth Intl. to Albany Intl., returning Wed, Jun 11, priced at $221 found 11 hours ago
Delta
Sun, Jun 8 - Tue, Jun 10
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$241 Roundtrip, found 11 hours ago
$241
Roundtrip
found 11 hours ago
Select Delta flight, departing Sun, Jun 8 from Dallas-Fort Worth Intl. to Albany Intl., returning Tue, Jun 10, priced at $241 found 11 hours ago
American Airlines
Fri, Jun 6 - Wed, Jun 11
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$273 Roundtrip, found 11 hours ago
$273
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Fri, Jun 6 from Dallas-Fort Worth Intl. to Albany Intl., returning Wed, Jun 11, priced at $273 found 11 hours ago
Delta
Sat, Jun 7 - Mon, Jun 9
DAL
Love Field
ALB
Albany Intl.
$283 Roundtrip, found 11 hours ago
$283
Roundtrip
found 11 hours ago
Select Delta flight, departing Sat, Jun 7 from Love Field to Albany Intl., returning Mon, Jun 9, priced at $283 found 11 hours ago
Delta
Tue, Jul 8 - Tue, Jul 15
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$285 Roundtrip, found 13 hours ago
$285
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Jul 8 from Southwest Florida Intl. to Albany Intl., returning Tue, Jul 15, priced at $285 found 13 hours ago
American Airlines
Tue, Jul 8 - Tue, Jul 15
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$289 Roundtrip, found 13 hours ago
$289
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Tue, Jul 8 from Southwest Florida Intl. to Albany Intl., returning Tue, Jul 15, priced at $289 found 13 hours ago
Delta
Tue, Jul 8 - Sat, Jul 12
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$301 Roundtrip, found 13 hours ago
$301
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Jul 8 from Southwest Florida Intl. to Albany Intl., returning Sat, Jul 12, priced at $301 found 13 hours ago
American Airlines
Fri, Jun 6 - Mon, Jun 9
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$303 Roundtrip, found 11 hours ago
$303
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Fri, Jun 6 from Dallas-Fort Worth Intl. to Albany Intl., returning Mon, Jun 9, priced at $303 found 11 hours ago
American Airlines
Tue, Jul 8 - Tue, Jul 15
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$306 Roundtrip, found 13 hours ago
$306
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Tue, Jul 8 from Southwest Florida Intl. to Albany Intl., returning Tue, Jul 15, priced at $306 found 13 hours ago
American Airlines
Fri, Jun 6 - Wed, Jun 11
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$311 Roundtrip, found 11 hours ago
$311
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Fri, Jun 6 from Dallas-Fort Worth Intl. to Albany Intl., returning Wed, Jun 11, priced at $311 found 11 hours ago
American Airlines
Tue, May 27 - Tue, Jun 3
SJO
Juan Santamaría Intl.
ALB
Albany Intl.
$320 Roundtrip, found 1 day ago
$320
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, May 27 from Juan Santamaría Intl. to Albany Intl., returning Tue, Jun 3, priced at $320 found 1 day ago
United
Sat, May 24 - Thu, Jun 5
SJO
Juan Santamaría Intl.
ALB
Albany Intl.
$355 Roundtrip, found 1 day ago
$355
Roundtrip
found 1 day ago
Select United flight, departing Sat, May 24 from Juan Santamaría Intl. to Albany Intl., returning Thu, Jun 5, priced at $355 found 1 day ago
Breeze Airways
Sun, Jul 6 - Thu, Jul 17
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$373 Roundtrip, found 13 hours ago
$373
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Sun, Jul 6 from Southwest Florida Intl. to Albany Intl., returning Thu, Jul 17, priced at $373 found 13 hours ago
JetBlue Airways
Sat, Jun 14 - Mon, Jun 16
LAS
Harry Reid Intl.
ALB
Albany Intl.
$386 Roundtrip, found 1 day ago
$386
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Jun 14 from Harry Reid Intl. to Albany Intl., returning Mon, Jun 16, priced at $386 found 1 day ago
Delta
Mon, Dec 22 - Sun, Dec 28
ABQ
Albuquerque Intl. Sunport
ALB
Albany Intl.
$747 Roundtrip, found 12 hours ago
$747
Roundtrip
found 12 hours ago
Select Delta flight, departing Mon, Dec 22 from Albuquerque Intl. Sunport to Albany Intl., returning Sun, Dec 28, priced at $747 found 12 hours ago
Alaska Airlines
Sun, Jun 15 - Wed, Jun 18
LAS
Harry Reid Intl.
ALB
Albany Intl.
$1,183 Roundtrip, found 1 day ago
$1,183
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sun, Jun 15 from Harry Reid Intl. to Albany Intl., returning Wed, Jun 18, priced at $1,183 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 16 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 $221, 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 $221 right now, why wait?

Cheshire Flight Information
Destination airport
Albany Intl.
Destination airport IATA code
ALB
Roundtrip price
$221

Last Minute Hotel Deals in Cheshire

Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is $115 per night from May 4 to May 5
$115
includes taxes & fees
May 4 - May 5
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! (573 reviews)
Beautiful & Affordable!
"Excellent experience and gorgeous property! Will stay again next time we visit the Berkshires."

Reviewed on Apr 27, 2025

Life House 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 $134 per night from May 14 to May 15
$134
includes taxes & fees
May 14 - May 15
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! (627 reviews)
"Friendly staffs. Home away from home. No elevators (the only inconvenience)!"

Reviewed on Apr 28, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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 $120 per night from May 4 to May 5
$120
includes taxes & fees
May 4 - May 5
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! (1,000 reviews)
"It is convenient"

Reviewed on Apr 29, 2025

The Yankee, Trademark Collection by Wyndham
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! (1,002 reviews)
"Staffs were very friendly especially the lady ( I apologize I didn't get her name) in the breakfast buffet was super nice. The accommodations were dated but was very comfortable and clean. The room was well maintained."

Reviewed on Apr 29, 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection
Hotel Downstreet, Ascend Hotel Collection
Hotel Downstreet, Ascend Hotel Collection
3 out of 5
40 Main St, North Adams, MA
The price is $141 per night from May 4 to May 5
$141
includes taxes & fees
May 4 - May 5
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! (999 reviews)
"Very nice and funky place! Clean, friendly nice staff. Have already stayed here twice and plan to stay again!❤️"

Reviewed on Apr 18, 2025

Hotel Downstreet, Ascend Hotel Collection
The Williams Inn
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
The price is $334 per night from May 4 to May 5
$334
includes taxes & fees
May 4 - May 5
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! (447 reviews)
"Wonderful staff! Welcoming, relaxed, great personalities."

Reviewed on Apr 28, 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 4 to May 5
$211
includes taxes & fees
May 4 - May 5
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
The Constance, The Whitlock, & The Dewey By The Lenox Collection
The Constance, The Whitlock, & The Dewey By The Lenox Collection
3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
The price is $91 per night from May 4 to May 5
$91
includes taxes & fees
May 4 - May 5
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.6/10 Excellent! (387 reviews)
"Receptionist was excellent. The room had the smell of an old building so we opened the windows to air it out and then it was fine. A night stand was damaged so we informed the receptionist but overall we were comfortable."

Reviewed on Apr 27, 2025

The Constance, The Whitlock, & The Dewey By The Lenox Collection
See all 980 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.