Search Cheap Flights to
Cheshire

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Cheshire Flights as Low as $138

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

Breeze Airways
Thu, Aug 28 - Sun, Aug 31
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$138 Roundtrip, found 11 hours ago
$138
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Thu, Aug 28 from Raleigh - Durham Intl. to Albany Intl., returning Sun, Aug 31, priced at $138 found 11 hours ago
Breeze Airways
Thu, Aug 28 - Sun, Aug 31
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$143 Roundtrip, found 11 hours ago
$143
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Thu, Aug 28 from Raleigh - Durham Intl. to Albany Intl., returning Sun, Aug 31, priced at $143 found 11 hours ago
American Airlines
Wed, Sep 3 - Thu, Sep 4
MCO
Orlando Intl.
ALB
Albany Intl.
$146 Roundtrip, found 16 hours ago
$146
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Wed, Sep 3 from Orlando Intl. to Albany Intl., returning Thu, Sep 4, priced at $146 found 16 hours ago
Breeze Airways
Thu, Aug 28 - Sun, Aug 31
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$148 Roundtrip, found 11 hours ago
$148
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Thu, Aug 28 from Raleigh - Durham Intl. to Albany Intl., returning Sun, Aug 31, priced at $148 found 11 hours ago
Breeze Airways
Thu, Sep 4 - Tue, Sep 9
MCO
Orlando Intl.
ALB
Albany Intl.
$152 Roundtrip, found 18 hours ago
$152
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Thu, Sep 4 from Orlando Intl. to Albany Intl., returning Tue, Sep 9, priced at $152 found 18 hours ago
JetBlue Airways
Wed, Sep 3 - Thu, Sep 4
MCO
Orlando Intl.
ALB
Albany Intl.
$154 Roundtrip, found 16 hours ago
$154
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Wed, Sep 3 from Orlando Intl. to Albany Intl., returning Thu, Sep 4, priced at $154 found 16 hours ago
JetBlue Airways
Wed, Nov 5 - Tue, Nov 11
MCO
Orlando Intl.
ALB
Albany Intl.
$157 Roundtrip, found 16 hours ago
$157
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Wed, Nov 5 from Orlando Intl. to Albany Intl., returning Tue, Nov 11, priced at $157 found 16 hours ago
JetBlue Airways
Wed, Sep 3 - Sat, Sep 6
MCO
Orlando Intl.
ALB
Albany Intl.
$159 Roundtrip, found 1 day ago
$159
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Sep 3 from Orlando Intl. to Albany Intl., returning Sat, Sep 6, priced at $159 found 1 day ago
American Airlines
Tue, Sep 23 - Tue, Sep 30
MCO
Orlando Intl.
ALB
Albany Intl.
$167 Roundtrip, found 15 hours ago
$167
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Tue, Sep 23 from Orlando Intl. to Albany Intl., returning Tue, Sep 30, priced at $167 found 15 hours ago
American Airlines
Sat, Sep 6 - Tue, Sep 9
ONT
Los Angeles - Ontario Intl.
ALB
Albany Intl.
$171 Roundtrip, found 3 days ago
$171
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Sep 6 from Los Angeles - Ontario Intl. to Albany Intl., returning Tue, Sep 9, priced at $171 found 3 days ago
Bargain Flight
Mon, Aug 25 - Wed, Sep 3
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$188 Roundtrip, found 13 hours ago
$188
Roundtrip
found 13 hours ago
Select Bargain Flight flight, departing Mon, Aug 25 from Raleigh - Durham Intl. to Albany Intl., returning Wed, Sep 3, priced at $188 found 13 hours ago
Delta
Tue, Sep 23 - Tue, Sep 30
MCO
Orlando Intl.
ALB
Albany Intl.
$197 Roundtrip, found 15 hours ago
$197
Roundtrip
found 15 hours ago
Select Delta flight, departing Tue, Sep 23 from Orlando Intl. to Albany Intl., returning Tue, Sep 30, priced at $197 found 15 hours ago
Bargain Flight
Mon, Sep 15 - Sat, Sep 20
IND
Indianapolis Intl.
ALB
Albany Intl.
$211 Roundtrip, found 10 hours ago
$211
Roundtrip
found 10 hours ago
Select Bargain Flight flight, departing Mon, Sep 15 from Indianapolis Intl. to Albany Intl., returning Sat, Sep 20, priced at $211 found 10 hours ago
American Airlines
Sat, Aug 9 - Fri, Aug 15
LAX
Los Angeles Intl.
ALB
Albany Intl.
$231 Roundtrip, found 5 days ago
$231
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug 9 from Los Angeles Intl. to Albany Intl., returning Fri, Aug 15, priced at $231 found 5 days ago
American Airlines
Tue, Aug 26 - Sat, Aug 30
SFO
San Francisco Intl.
ALB
Albany Intl.
$239 Roundtrip, found 7 hours ago
$239
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Tue, Aug 26 from San Francisco Intl. to Albany Intl., returning Sat, Aug 30, priced at $239 found 7 hours ago
Alaska Airlines
Sat, Sep 6 - Tue, Sep 9
ONT
Los Angeles - Ontario Intl.
ALB
Albany Intl.
$831 Roundtrip, found 3 days ago
$831
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Sat, Sep 6 from Los Angeles - Ontario Intl. to Albany Intl., returning Tue, Sep 9, priced at $831 found 3 days 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 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 $138, 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 $138 right now, why wait?

Cheshire Flight Information
Destination airport
Albany Intl.
Destination airport IATA code
ALB
Roundtrip price
$138

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! (1,868 reviews)
"Wonderful property in an idyllic setting! Everything you need for a quality vacation with friends or family. One of the most relaxing getaways I've ever had."

Reviewed on Jul 11, 2025

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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! (465 reviews)
"Hrwat"

Reviewed on Jul 11, 2025

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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! (1,000 reviews)
Pleasant
"Spacious room with a great view, only complaint would be the gaps in the door that let noise and light in and out."

Reviewed on Jul 8, 2025

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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! (1,012 reviews)
"Great"

Reviewed on Jul 13, 2025

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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! (631 reviews)
"I’ve stayed at this property several times including before it changed management. We have always enjoyed everything about it. My only strong suggestion is that there is better signage out by the highway. You do not see the hotel or the sign until you get very close to the turn and it is a very busy ..."

Reviewed on Jul 10, 2025

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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! (670 reviews)
"Rooms need renovation but a nice property"

Reviewed on Jul 11, 2025

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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! (818 reviews)
"Clean but needs renovations"

Reviewed on Jul 8, 2025

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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 (739 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

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FairBridge Inn Express
See all 1,002 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.