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Cheshire

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Cheshire Flights as Low as $174

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

Breeze Airways
Thu, Apr 30 - Tue, May 5
MCO
Orlando Intl.
ALB
Albany Intl.
$174 Roundtrip, found 1 hour ago
$174
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Apr 30 from Orlando Intl. to Albany Intl., returning Tue, May 5, priced at $174 found 1 hour ago
Breeze Airways
Thu, Apr 30 - Tue, May 5
MCO
Orlando Intl.
ALB
Albany Intl.
$179 Roundtrip, found 1 hour ago
$179
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Apr 30 from Orlando Intl. to Albany Intl., returning Tue, May 5, priced at $179 found 1 hour ago
Breeze Airways
Thu, Apr 30 - Tue, May 5
MCO
Orlando Intl.
ALB
Albany Intl.
$184 Roundtrip, found 1 hour ago
$184
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Apr 30 from Orlando Intl. to Albany Intl., returning Tue, May 5, priced at $184 found 1 hour ago
JetBlue Airways
Wed, Jun 3 - Tue, Jun 9
MCO
Orlando Intl.
ALB
Albany Intl.
$207 Roundtrip, found 4 hours ago
$207
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Wed, Jun 3 from Orlando Intl. to Albany Intl., returning Tue, Jun 9, priced at $207 found 4 hours ago
Breeze Airways
Fri, May 1 - Tue, May 5
MCO
Orlando Intl.
ALB
Albany Intl.
$210 Roundtrip, found 4 hours ago
$210
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Fri, May 1 from Orlando Intl. to Albany Intl., returning Tue, May 5, priced at $210 found 4 hours ago
Delta
Thu, Apr 30 - Tue, May 5
MCO
Orlando Intl.
ALB
Albany Intl.
$211 Roundtrip, found 1 hour ago
$211
Roundtrip
found 1 hour ago
Select Delta flight, departing Thu, Apr 30 from Orlando Intl. to Albany Intl., returning Tue, May 5, priced at $211 found 1 hour ago
Delta
Thu, May 7 - Wed, May 13
MCO
Orlando Intl.
ALB
Albany Intl.
$227 Roundtrip, found 1 hour ago
$227
Roundtrip
found 1 hour ago
Select Delta flight, departing Thu, May 7 from Orlando Intl. to Albany Intl., returning Wed, May 13, priced at $227 found 1 hour ago
United
Thu, Apr 30 - Tue, May 5
MCO
Orlando Intl.
ALB
Albany Intl.
$231 Roundtrip, found 1 hour ago
$231
Roundtrip
found 1 hour ago
Select United flight, departing Thu, Apr 30 from Orlando Intl. to Albany Intl., returning Tue, May 5, priced at $231 found 1 hour ago
American Airlines
Wed, May 13 - Wed, May 20
GSP
Greenville-Spartanburg Intl.
ALB
Albany Intl.
$266 Roundtrip, found 5 days ago
$266
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, May 13 from Greenville-Spartanburg Intl. to Albany Intl., returning Wed, May 20, priced at $266 found 5 days ago
American Airlines
Thu, May 7 - Wed, May 13
MCO
Orlando Intl.
ALB
Albany Intl.
$287 Roundtrip, found 1 hour ago
$287
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, May 7 from Orlando Intl. to Albany Intl., returning Wed, May 13, priced at $287 found 1 hour ago
Bargain Flight
Tue, Aug 4 - Wed, Aug 12
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$291 Roundtrip, just found
$291
Roundtrip
just found
Select Bargain Flight flight, departing Tue, Aug 4 from Dallas-Fort Worth Intl. to Albany Intl., returning Wed, Aug 12, priced at $291 just found
Bargain Flight
Mon, Apr 27 - Mon, May 4
PHX
Sky Harbor Intl.
ALB
Albany Intl.
$313 Roundtrip, found 11 hours ago
$313
Roundtrip
found 11 hours ago
Select Bargain Flight flight, departing Mon, Apr 27 from Sky Harbor Intl. to Albany Intl., returning Mon, May 4, priced at $313 found 11 hours ago
American Airlines
Tue, Apr 21 - Sat, Apr 25
SFO
San Francisco Intl.
ALB
Albany Intl.
$317 Roundtrip, found 1 day ago
$317
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Apr 21 from San Francisco Intl. to Albany Intl., returning Sat, Apr 25, priced at $317 found 1 day ago
Delta
Tue, Aug 4 - Wed, Aug 12
DAL
Love Field
ALB
Albany Intl.
$433 Roundtrip, just found
$433
Roundtrip
just found
Select Delta flight, departing Tue, Aug 4 from Love Field to Albany Intl., returning Wed, Aug 12, priced at $433 just found
Alaska Airlines
Tue, Apr 21 - Sat, Apr 25
SFO
San Francisco Intl.
ALB
Albany Intl.
$496 Roundtrip, found 1 day ago
$496
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Apr 21 from San Francisco Intl. to Albany Intl., returning Sat, Apr 25, priced at $496 found 1 day ago
Delta
Wed, Apr 29 - Wed, May 6
ANC
Ted Stevens Anchorage Intl.
ALB
Albany Intl.
$718 Roundtrip, found 1 day ago
$718
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Apr 29 from Ted Stevens Anchorage Intl. to Albany Intl., returning Wed, May 6, priced at $718 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 April, 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 $174, 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 $174 right now, why wait?

Cheshire Flight Information
Destination airport
Albany Intl.
Destination airport IATA code
ALB
Roundtrip price
$173

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 WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
8.8/10 Excellent! (1,000 reviews)
Great location. Within walking distance to MOCA, and a few restaurants that were open during our stay. The town is post industrial and post manufacturing. Walking around MOCA is a wonderful experience in itself as much of the history of the building and surrounding area comes alive and is fascinating.The ...

Reviewed on Mar 22, 2026

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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! (892 reviews)
Clean, quiet, spacious, comfortable, and lovely furnishings! It was a very relaxing overnight.

Reviewed on Mar 31, 2026

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Berkshire Mountain Lodge
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! (884 reviews)
Easy check-in, secure and clean

Reviewed on Mar 30, 2026

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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
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 ...
9/10 Wonderful! (860 reviews)
this has been absolutely amazing and incredible for incredibly difficult time for our family because of family medical emergency. everyone has been so amazing and beautiful and healing for our loved ones and we are grateful to be close to then

Reviewed on Apr 1, 2026

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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
Book a stay at this 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! (603 reviews)
We went on a freezing cold February weekend and it was amazing!! Inn was cozy and clean, just gorgeous with its lobby fireplace and immaculate room. Best part was having dinner at The Barn and heading up the stairs to watch the Olympics in our toasty warm room. Will definitely book again and recommend ...

Reviewed on Apr 1, 2026

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The Williams Inn
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd Williamstown MA
Stay at this campground in Williamstown. Enjoy free parking, breakfast (surcharge), and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
9.4/10 Exceptional! (10 reviews)
Excelente servicio

Reviewed on Mar 8, 2026

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Huttopia Berkshires
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

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! (1,002 reviews)
Room was comfortable and quiet. Staff accommodated a request to change rooms after check-in as we discovered there was someone next door who was constantly on the phone speaking loudly in a voice that carried on something business related. Relocating us was very appreciated.

Reviewed on Mar 26, 2026

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The Yankee, Trademark Collection by Wyndham
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
9.2/10 Wonderful! (1,001 reviews)
Breakfast is excellent, quiet place is peaceful you can relax really well it has an Indian cuisine restaurant inside also a bar the restaurant is excellent all you request they will do it as long that they have it they will do everything is excellent to this In. Friendly staff.

Reviewed on Mar 30, 2026

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The Black Swan Lee - Lenox, an Ascend Collection Hotel
See all 1,022 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.