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Cheshire

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Cheshire Flights as Low as $74

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

Frontier Airlines
Thu, May 29 - Sat, May 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$74 Roundtrip, found 23 hours ago
$74
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Thu, May 29 from Orlando Intl. to Bradley Intl., returning Sat, May 31, priced at $74 found 23 hours ago
Frontier Airlines
Thu, May 29 - Mon, Jun 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$80 Roundtrip, found 23 hours ago
$80
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Thu, May 29 from Orlando Intl. to Bradley Intl., returning Mon, Jun 2, priced at $80 found 23 hours ago
Frontier Airlines
Thu, May 29 - Sun, Jun 1
MCO
Orlando Intl.
BDL
Bradley Intl.
$85 Roundtrip, found 23 hours ago
$85
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Thu, May 29 from Orlando Intl. to Bradley Intl., returning Sun, Jun 1, priced at $85 found 23 hours ago
Frontier Airlines
Thu, May 15 - Mon, May 19
MCO
Orlando Intl.
BDL
Bradley Intl.
$88 Roundtrip, found 1 day ago
$88
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, May 15 from Orlando Intl. to Bradley Intl., returning Mon, May 19, priced at $88 found 1 day ago
Frontier Airlines
Fri, May 16 - Sat, May 17
MCO
Orlando Intl.
BDL
Bradley Intl.
$89 Roundtrip, found 7 hours ago
$89
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Fri, May 16 from Orlando Intl. to Bradley Intl., returning Sat, May 17, priced at $89 found 7 hours ago
Frontier Airlines
Sun, Jun 15 - Sun, Jun 22
MCO
Orlando Intl.
BDL
Bradley Intl.
$97 Roundtrip, found 4 days ago
$97
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Jun 15 from Orlando Intl. to Bradley Intl., returning Sun, Jun 22, priced at $97 found 4 days ago
Spirit Airlines
Fri, May 30 - Mon, Jun 2
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$98 Roundtrip, found 6 days ago
$98
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Fri, May 30 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Jun 2, priced at $98 found 6 days ago
Spirit Airlines
Thu, May 29 - Sun, Jun 1
MCO
Orlando Intl.
BDL
Bradley Intl.
$99 Roundtrip, found 23 hours ago
$99
Roundtrip
found 23 hours ago
Select Spirit Airlines flight, departing Thu, May 29 from Orlando Intl. to Bradley Intl., returning Sun, Jun 1, priced at $99 found 23 hours ago
Frontier Airlines
Thu, May 29 - Fri, May 30
MCO
Orlando Intl.
BDL
Bradley Intl.
$100 Roundtrip, found 23 hours ago
$100
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Thu, May 29 from Orlando Intl. to Bradley Intl., returning Fri, May 30, priced at $100 found 23 hours ago
Breeze Airways
Thu, May 15 - Mon, May 19
MCO
Orlando Intl.
BDL
Bradley Intl.
$125 Roundtrip, found 1 day ago
$125
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, May 15 from Orlando Intl. to Bradley Intl., returning Mon, May 19, priced at $125 found 1 day ago
JetBlue Airways
Tue, Jun 10 - Tue, Jun 10
MCO
Orlando Intl.
BDL
Bradley Intl.
$144 Roundtrip, found 4 days ago
$144
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Jun 10 from Orlando Intl. to Bradley Intl., returning Tue, Jun 10, priced at $144 found 4 days ago
American Airlines
Fri, May 30 - Mon, Jun 2
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$161 Roundtrip, found 6 days ago
$161
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, May 30 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Jun 2, priced at $161 found 6 days ago
Delta
Wed, Jul 2 - Mon, Jul 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$200 Roundtrip, found 2 days ago
$200
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jul 2 from Orlando Intl. to Bradley Intl., returning Mon, Jul 7, priced at $200 found 2 days ago
United
Fri, May 16 - Sun, May 18
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$206 Roundtrip, found 1 day ago
$206
Roundtrip
found 1 day ago
Select United flight, departing Fri, May 16 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Sun, May 18, priced at $206 found 1 day ago
United
Fri, May 30 - Mon, Jun 2
RNO
Reno-Tahoe Intl.
BDL
Bradley Intl.
$291 Roundtrip, found 1 day ago
$291
Roundtrip
found 1 day ago
Select United flight, departing Fri, May 30 from Reno-Tahoe Intl. to Bradley Intl., returning Mon, Jun 2, priced at $291 found 1 day ago
Alaska Airlines
Fri, May 30 - Mon, Jun 2
RNO
Reno-Tahoe Intl.
BDL
Bradley Intl.
$565 Roundtrip, found 1 day ago
$565
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Fri, May 30 from Reno-Tahoe Intl. to Bradley Intl., returning Mon, Jun 2, priced at $565 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 BDL 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 May, 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 Waterbury - Oxford 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 $74, 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 $74 right now, why wait?

Last Minute Hotel Deals in Cheshire

Holiday Inn Cheshire - Southington by IHG
Holiday Inn Cheshire - Southington by IHG
3 out of 5
64 Knotter Dr, Cheshire, CT
Stay at this 3-star business-friendly hotel in Cheshire. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.2/10 Very Good! (1,000 reviews)
"Good environment excellent customer service an support"

Reviewed on May 2, 2025

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Holiday Inn Cheshire - Southington by IHG
Cheshire Welcome Inn
Cheshire Welcome Inn
2.5 out of 5
1106 S Main St., Cheshire, CT
Stay at this motel in Cheshire. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (666 reviews)
"Great stay would stay again only problem people smoking next door and my room smelt like an Astray they shouldn’t be allowed to smoke outside the room because it’s so close to other rooms should be a distance from property designated area"

Reviewed on May 4, 2025

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Cheshire Welcome Inn
New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
Stay at this 3.5-star business-friendly hotel in New Haven. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,516 reviews)
"This hotel is a ten-minute walk from Union Station New Haven"

Reviewed on May 6, 2025

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New Haven Hotel
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.4/10 Good! (1,001 reviews)
"Awsome"

Reviewed on May 6, 2025

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Clarion Inn
Holiday Inn Express Southington by IHG
Holiday Inn Express Southington by IHG
2.5 out of 5
120 Laning St, Southington, CT
Book a stay at this business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,012 reviews)
"Staff was extremely helpful and efficient. Room was very clean.. easy parking, easy access to dining facilities and highways.. will definitely stay here again"

Reviewed on May 7, 2025

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Holiday Inn Express Southington by IHG
Cambria Hotel New Haven University Area
Cambria Hotel New Haven University Area
3 out of 5
20 Dwight Street, New Haven, CT
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
8.8/10 Excellent! (727 reviews)
"Great hotel stay!"

Reviewed on May 7, 2025

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Cambria Hotel New Haven University Area
Omni New Haven Hotel at Yale
Omni New Haven Hotel at Yale
4 out of 5
155 Temple St, New Haven, CT
Stay at this 4-star business-friendly hotel in New Haven. Enjoy 2 restaurants, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,000 reviews)
"Check in was fast and staff friendly. Not very happy with $25 parking fee. Dining on the 19th floor was enjoyable. Dan the bartender very cordial."

Reviewed on May 4, 2025

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Omni New Haven Hotel at Yale
Hyatt Place Milford / New Haven
Hyatt Place Milford / New Haven
3 out of 5
190 Old Gate Lane, Milford, CT
Stay at this 3-star business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,006 reviews)
"Clean building"

Reviewed on May 7, 2025

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Hyatt Place Milford / New Haven
See all 1,151 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.