Search Cheap Flights to
Cheshire

Photo by Ed Gaffny

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Cheshire Flights as Low as $137

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

JetBlue Airways
Tue, Aug 19 - Tue, Aug 26
MCO
Orlando Intl.
ALB
Albany Intl.
$137 Roundtrip, found 14 hours ago
$137
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Tue, Aug 19 from Orlando Intl. to Albany Intl., returning Tue, Aug 26, priced at $137 found 14 hours ago
Breeze Airways
Thu, Sep 4 - Tue, Sep 9
MCO
Orlando Intl.
ALB
Albany Intl.
$139 Roundtrip, found 7 hours ago
$139
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Thu, Sep 4 from Orlando Intl. to Albany Intl., returning Tue, Sep 9, priced at $139 found 7 hours ago
Breeze Airways
Thu, Aug 28 - Sun, Aug 31
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$142 Roundtrip, found 17 hours ago
$142
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Thu, Aug 28 from Raleigh - Durham Intl. to Albany Intl., returning Sun, Aug 31, priced at $142 found 17 hours ago
Breeze Airways
Thu, Sep 4 - Sat, Sep 6
MCO
Orlando Intl.
ALB
Albany Intl.
$143 Roundtrip, found 2 days ago
$143
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Sep 4 from Orlando Intl. to Albany Intl., returning Sat, Sep 6, priced at $143 found 2 days ago
Breeze Airways
Thu, Sep 4 - Tue, Sep 9
MCO
Orlando Intl.
ALB
Albany Intl.
$144 Roundtrip, found 7 hours ago
$144
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Thu, Sep 4 from Orlando Intl. to Albany Intl., returning Tue, Sep 9, priced at $144 found 7 hours ago
American Airlines
Wed, Sep 3 - Thu, Sep 4
MCO
Orlando Intl.
ALB
Albany Intl.
$146 Roundtrip, found 4 days ago
$146
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Sep 3 from Orlando Intl. to Albany Intl., returning Thu, Sep 4, priced at $146 found 4 days ago
American Airlines
Tue, Aug 19 - Tue, Aug 26
MCO
Orlando Intl.
ALB
Albany Intl.
$148 Roundtrip, found 14 hours ago
$148
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Tue, Aug 19 from Orlando Intl. to Albany Intl., returning Tue, Aug 26, priced at $148 found 14 hours ago
Breeze Airways
Thu, Sep 4 - Sat, Sep 6
MCO
Orlando Intl.
ALB
Albany Intl.
$148 Roundtrip, found 2 days ago
$148
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Sep 4 from Orlando Intl. to Albany Intl., returning Sat, Sep 6, priced at $148 found 2 days ago
Breeze Airways
Thu, Aug 28 - Sun, Aug 31
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$152 Roundtrip, found 17 hours ago
$152
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Thu, Aug 28 from Raleigh - Durham Intl. to Albany Intl., returning Sun, Aug 31, priced at $152 found 17 hours ago
JetBlue Airways
Tue, Aug 5 - Thu, Aug 14
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$157 Roundtrip, found 14 hours ago
$157
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Tue, Aug 5 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Thu, Aug 14, priced at $157 found 14 hours ago
American Airlines
Tue, Aug 19 - Tue, Aug 26
MCO
Orlando Intl.
ALB
Albany Intl.
$159 Roundtrip, found 14 hours ago
$159
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Tue, Aug 19 from Orlando Intl. to Albany Intl., returning Tue, Aug 26, priced at $159 found 14 hours ago
Bargain Flight
Mon, Aug 25 - Wed, Sep 3
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$188 Roundtrip, found 1 day ago
$188
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Mon, Aug 25 from Raleigh - Durham Intl. to Albany Intl., returning Wed, Sep 3, priced at $188 found 1 day ago
Delta
Tue, Sep 23 - Tue, Sep 30
MCO
Orlando Intl.
ALB
Albany Intl.
$197 Roundtrip, found 1 hour ago
$197
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Sep 23 from Orlando Intl. to Albany Intl., returning Tue, Sep 30, priced at $197 found 1 hour ago
Delta
Tue, Sep 23 - Sat, Sep 27
CMH
John Glenn Columbus Intl.
ALB
Albany Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 23 from John Glenn Columbus Intl. to Albany Intl., returning Sat, Sep 27, priced at $237 found 1 day ago
Delta
Wed, Oct 15 - Wed, Oct 22
GSP
Greenville-Spartanburg Intl.
ALB
Albany Intl.
$237 Roundtrip, found 4 days ago
$237
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Oct 15 from Greenville-Spartanburg Intl. to Albany Intl., returning Wed, Oct 22, priced at $237 found 4 days ago
Delta
Tue, Aug 5 - Tue, Aug 5
AUS
Austin-Bergstrom Intl.
ALB
Albany Intl.
$521 Roundtrip, found 17 hours ago
$521
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Aug 5 from Austin-Bergstrom Intl. to Albany Intl., returning Tue, Aug 5, priced at $521 found 17 hours 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 August, 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 $137, 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 $137 right now, why wait?

Cheshire Flight Information
Destination airport
Albany Intl.
Destination airport IATA code
ALB
Roundtrip price
$137

Last Minute Hotel Deals in Cheshire

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,874 reviews)
"Great stay with all plenty of things to do…"

Reviewed on Jul 14, 2025

Get rates
Vacation Village in the Berkshires
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
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! (467 reviews)
"Hrwat"

Reviewed on Jul 11, 2025

Get rates
The Williams Inn
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
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! (1,003 reviews)
"Very convenient hotel close to all attractions. It also has a wonderful view of the mountains"

Reviewed on Jul 14, 2025

Get rates
Hotel Downstreet, Ascend Hotel Collection
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,013 reviews)
"Friendliness and cleanliness"

Reviewed on Jul 15, 2025

Get rates
Best Western Plus Berkshire Hills Inn & Suites
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
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! (633 reviews)
"It was ok for a one night"

Reviewed on Jul 15, 2025

Get rates
Berkshires Untold
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
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! (673 reviews)
"Wonderful SPACIOUS spotless unit with full kitchen, table and chair set, lovely forest view deck, two bathrooms, separate bedrooms and a comfortable sleep sofa!! Only problem was that there was no elevator to take our pieces of luggage to the third level. And we are Senior citizens! Otherwise, a ..."

Reviewed on Jul 14, 2025

Get rates
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (821 reviews)
Comfy beds, chair, good closet, very clean
"Overnight stay while on a family visit. Comfortable room, good beds, great AC. Quiet as well."

Reviewed on Jul 13, 2025

Get rates
Holiday Inn & Suites Pittsfield-Berkshires by IHG
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
5.2/10 (741 reviews)
"Rooms were much nicer than expected. Despite the somewhat dated exterior and overall first impression from the outside, the rooms were solidly good, clean, and comfortable. Good value for the price."

Reviewed on Jul 1, 2025

Get rates
FairBridge Inn Express
See all 1,009 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.