Search Cheap Flights to
Cheshire

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Cheshire Flights as Low as $181

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

JetBlue Airways
Mon, Jul 27 - Wed, Aug 5
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$181 Roundtrip, found 2 days ago
$181
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Mon, Jul 27 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Wed, Aug 5, priced at $181 found 2 days ago
American Airlines
Tue, Jul 7 - Fri, Jul 10
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$207 Roundtrip, found 22 hours ago
$207
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Tue, Jul 7 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Fri, Jul 10, priced at $207 found 22 hours ago
Delta
Mon, Jul 27 - Wed, Aug 5
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$212 Roundtrip, found 2 days ago
$212
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Jul 27 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Wed, Aug 5, priced at $212 found 2 days ago
JetBlue Airways
Mon, Aug 3 - Wed, Aug 5
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$212 Roundtrip, found 3 days ago
$212
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Aug 3 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Wed, Aug 5, priced at $212 found 3 days ago
JetBlue Airways
Mon, Jul 27 - Thu, Aug 6
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$217 Roundtrip, found 3 days ago
$217
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Jul 27 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Thu, Aug 6, priced at $217 found 3 days ago
Delta
Wed, Jul 8 - Fri, Jul 10
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$222 Roundtrip, found 18 hours ago
$222
Roundtrip
found 18 hours ago
Select Delta flight, departing Wed, Jul 8 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Fri, Jul 10, priced at $222 found 18 hours ago
American Airlines
Tue, Jul 7 - Fri, Jul 10
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$222 Roundtrip, found 22 hours ago
$222
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Tue, Jul 7 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Fri, Jul 10, priced at $222 found 22 hours ago
JetBlue Airways
Mon, Aug 3 - Thu, Aug 6
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$229 Roundtrip, found 3 days ago
$229
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Aug 3 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Thu, Aug 6, priced at $229 found 3 days ago
Bargain Flight
Wed, Nov 4 - Tue, Nov 17
TPA
Tampa Intl.
ALB
Albany Intl.
$264 Roundtrip, just found
$264
Roundtrip
just found
Select Bargain Flight flight, departing Wed, Nov 4 from Tampa Intl. to Albany Intl., returning Tue, Nov 17, priced at $264 just found
Delta
Tue, Sep 22 - Tue, Oct 6
SAV
Savannah - Hilton Head Intl.
ALB
Albany Intl.
$317 Roundtrip, found 1 day ago
$317
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 22 from Savannah - Hilton Head Intl. to Albany Intl., returning Tue, Oct 6, priced at $317 found 1 day ago
Breeze Airways
Thu, Jul 2 - Thu, Jul 16
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$389 Roundtrip, found 3 days ago
$389
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jul 2 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Thu, Jul 16, priced at $389 found 3 days ago
Bargain Flight
Sun, Jun 21 - Thu, Jun 25
CLE
Hopkins Intl.
ALB
Albany Intl.
$453 Roundtrip, found 1 day ago
$453
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sun, Jun 21 from Hopkins Intl. to Albany Intl., returning Thu, Jun 25, priced at $453 found 1 day ago
American Airlines
Wed, Jun 24 - Tue, Jun 30
CLD
McClellan-Palomar
ALB
Albany Intl.
$596 Roundtrip, just found
$596
Roundtrip
just found
Select American Airlines flight, departing Wed, Jun 24 from McClellan-Palomar to Albany Intl., returning Tue, Jun 30, priced at $596 just found
American Airlines
Tue, Jun 23 - Wed, Jul 1
IAH
George Bush Intercontinental
ALB
Albany Intl.
$611 Roundtrip, found 3 days ago
$611
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Jun 23 from George Bush Intercontinental to Albany Intl., returning Wed, Jul 1, priced at $611 found 3 days ago
United
Tue, Jun 23 - Fri, Jul 3
SAN
San Diego Intl.
ALB
Albany Intl.
$690 Roundtrip, found 3 days ago
$690
Roundtrip
found 3 days ago
Select United flight, departing Tue, Jun 23 from San Diego Intl. to Albany Intl., returning Fri, Jul 3, priced at $690 found 3 days ago
Alaska Airlines
Wed, Jun 24 - Tue, Jun 30
SAN
San Diego Intl.
ALB
Albany Intl.
$1,068 Roundtrip, found 1 day ago
$1,068
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Wed, Jun 24 from San Diego Intl. to Albany Intl., returning Tue, Jun 30, priced at $1,068 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 July, 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 14 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 $181, 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 $181 right now, why wait?

Cheshire Flight Information
Destination airport
Albany Intl.
Destination airport IATA code
ALB
Roundtrip price
$181

Last Minute Hotel Deals in Cheshire

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,004 reviews)
"Thank you, everything was perfect."

Reviewed on Jun 19, 2026

Get rates
Hotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (989 reviews)
"Location was perfect"

Reviewed on Jun 19, 2026

Get rates
Berkshire Mountain Lodge
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
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 ...
9.2/10 Wonderful! (1,001 reviews)
"A great hotel to stay in Berkshires. Close to everything we wanted: trails, cafes and restaurants, places of interest. Comfortable room again with everything we need in it. Amazing complex of in and outdoors pools, exercise room, hot tub, a decent breakfast. And an uncomparable per night price."

Reviewed on Jun 19, 2026

Get rates
The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,400 reviews)
"Had to keep getting new keycards they just wouldn't work on the inner door but were always fine on outer door to the double suites. Luckily I just left my porch door unlocked to go to the hot tub, I gave up after several new cards"

Reviewed on Jun 19, 2026

Get rates
Vacation Village in the Berkshires
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (989 reviews)
"I stayed for a short time, this had everything I needed and was reasonably priced. Room was a clean, had a comfy bed, was quiet, and very friendly staff to greet me both when I checked in and out… with yummy coffee in the morning. It’s a basic stay, but everything you need. Would definitely ..."

Reviewed on Jun 15, 2026

Get rates
Berkshires Untold
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,002 reviews)
"We thought we were booking a room at the Inn and expected to eat in the restaurant after a long day of travel. Our room was actually around the corner in an old house. ?We were underdressed for the restaurant (jeans, sneakers, decent shirts) and ate in the pub in the basement."

Reviewed on Jun 16, 2026

Get rates
The Red Lion Inn
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (866 reviews)
"The whole experience was great. Staff excellent."

Reviewed on Jun 16, 2026

Get rates
Hotel On North
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
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in ...
9.2/10 Wonderful! (913 reviews)
"Mini golf was amazing, as was having access to shuffleboard, cornhole and more. And the arcade was great, too, we went back many times! Room was clean and nice with it's own balcony and the resort was calm and quiet."

Reviewed on Jun 19, 2026

Get rates
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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.