Search Cheap Flights to
Cheshire

Name: Hilton Garden Inn Shelton
Rating: 8

Castle Craig at Hubbard Park, Meriden, CT. easily replaceable sky. with a clean, classic view of the tower. Very recognizable image of this historic structure.

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Cheshire Flights as Low as $107

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

All deals

One way

Roundtrip

Thu, Apr 23 - Sun, May 10

ORF

Norfolk Intl.

HVN

Tweed - New Haven Regional

$107

Roundtrip

found 6 hours ago

Thu, Apr 23 - Sun, May 10

ORF

Norfolk Intl.

HVN

Tweed - New Haven Regional

$108

Roundtrip

found 5 days ago

Thu, Apr 23 - Sun, May 10

ORF

Norfolk Intl.

HVN

Tweed - New Haven Regional

$112

Roundtrip

found 6 hours ago

Thu, Apr 23 - Sun, May 10

ORF

Norfolk Intl.

HVN

Tweed - New Haven Regional

$114

Roundtrip

found 5 days ago

Thu, Apr 23 - Sun, May 10

ORF

Norfolk Intl.

HVN

Tweed - New Haven Regional

$117

Roundtrip

found 6 hours ago

Thu, Apr 23 - Sun, May 10

ORF

Norfolk Intl.

HVN

Tweed - New Haven Regional

$119

Roundtrip

found 5 days ago

Thu, Apr 23 - Sun, May 10

ORF

Norfolk Intl.

HVN

Tweed - New Haven Regional

$122

Roundtrip

found 1 day ago

Fri, Apr 10 - Wed, Apr 22

RDU

Raleigh - Durham Intl.

HVN

Tweed - New Haven Regional

$122

Roundtrip

found 4 days ago

Thu, Apr 23 - Sun, May 10

ORF

Norfolk Intl.

HVN

Tweed - New Haven Regional

$124

Roundtrip

found 6 days ago

Wed, Jun 10 - Sun, Jun 14

RDU

Raleigh - Durham Intl.

BDL

Bradley Intl.

$147

Roundtrip

found 2 hours ago

Thu, Jun 11 - Mon, Jun 15

FLL

Fort Lauderdale - Hollywood Intl.

HVN

Tweed - New Haven Regional

$163

Roundtrip

found 1 day ago

Tue, Apr 7 - Mon, Apr 13

RDU

Raleigh - Durham Intl.

BDL

Bradley Intl.

$204

Roundtrip

found 4 hours ago

Thu, Apr 16 - Fri, Apr 24

FLL

Fort Lauderdale - Hollywood Intl.

BDL

Bradley Intl.

$210

Roundtrip

found 3 days ago

Tue, Jun 9 - Tue, Jun 16

FLL

Fort Lauderdale - Hollywood Intl.

BDL

Bradley Intl.

$227

Roundtrip

found 1 day ago

Tue, Jun 9 - Mon, Jun 15

FLL

Fort Lauderdale - Hollywood Intl.

BDL

Bradley Intl.

$247

Roundtrip

found 1 day ago

Thu, Apr 9 - Sun, Apr 26

FLL

Fort Lauderdale - Hollywood Intl.

BDL

Bradley Intl.

$261

Roundtrip

found 6 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 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 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 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 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 $107, 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 $107 right now, why wait?

Cheshire Flight Information
Destination airport	Bradley Intl.
Destination airport IATA code	BDL
Roundtrip price	$73

Last Minute Hotel Deals in Cheshire

New Haven Hotel

229 George Street New Haven CT

Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...

9/10 Wonderful! (2,066 reviews)

The check‑in process was very slow. Only one staff member was working, and although she was polite and friendly, the process took much longer than expected. She spent a lot of time explaining every detail, which made the wait even longer for guests in line. This definitely added to the overall check‑in ...

Reviewed on Apr 6, 2026

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Holiday Inn Express Southington by IHG

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! (1,258 reviews)

breakfast was fine did not use a/c

Reviewed on Mar 31, 2026

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The Capitol Hotel

440 Asylum St Hartford CT

Book a stay at this business-friendly hotel in Hartford. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...

7.6/10 Good! (1,225 reviews)

Got to the hotel....the Indian guy said I have a handicap room? Do I want to switch? I said sure he said he upgraded to a king... I'm like great. Got to the room it smelled a dead body.. the fan was blasting so I know they know the room stinks. It was a dirty wet, old carpet. Anyway I felt sorry ...

Reviewed on Apr 6, 2026

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Hyatt Place Milford / New Haven

190 Old Gate Lane Milford CT

Book a stay at this 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! (1,291 reviews)

Outdated, felt like a renovated motel

Reviewed on Apr 4, 2026

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Omni New Haven Hotel at Yale

155 Temple St New Haven CT

Book a stay at this business-friendly hotel in New Haven. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful ...

8.6/10 Excellent! (1,003 reviews)

Convenient location. Clean and great staff. Garage elevator was being upgraded so hard to get bags to lobby

Reviewed on Apr 6, 2026

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Hampton Inn & Suites Hartford/East Hartford

351 Pitkin Steet East Hartford CT

Stay at this hotel in East Hartford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...

9/10 Wonderful! (1,141 reviews)

Staff was very friendly.

Reviewed on Apr 5, 2026

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Hilton Garden Inn Shelton

25 Old Stratford Rd Shelton CT

Book a stay at this business-friendly hotel in Shelton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...

8/10 Very Good! (1,097 reviews)

clean rooms

Reviewed on Apr 6, 2026

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Motel 6 New Haven - Branford, CT

320 E Main St Branford CT

Stay at this motel in Branford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...

7.2/10 Good! (1,002 reviews)

Loved the nearby Italian restaurant where I had a lovely salad. Staff was pleasant. Water in the shower was dripping and it was dingy and looked dirty although it may have been cleaned. The linens seemed clean, probably the only redeeming quality. People were talking loudly in the hallways after ...

Reviewed on Apr 5, 2026

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See all 1,295 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.

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