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Cheshire

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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.

Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$107 Roundtrip, found 5 hours ago
$107
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $107 found 5 hours ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$108 Roundtrip, found 5 days ago
$108
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $108 found 5 days ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$112 Roundtrip, just found
$112
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $112 just found
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$114 Roundtrip, found 5 days ago
$114
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $114 found 5 days ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$117 Roundtrip, just found
$117
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $117 just found
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$119 Roundtrip, found 5 days ago
$119
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $119 found 5 days ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$122 Roundtrip, just found
$122
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $122 just found
Avelo Airlines
Fri, Apr 10 - Wed, Apr 22
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$122 Roundtrip, found 5 days ago
$122
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, Apr 22, priced at $122 found 5 days ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$124 Roundtrip, found 6 days ago
$124
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $124 found 6 days ago
Breeze Airways
Wed, Jun 10 - Sun, Jun 14
RDU
Raleigh - Durham Intl.
BDL
Bradley Intl.
$147 Roundtrip, found 12 hours ago
$147
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, Jun 10 from Raleigh - Durham Intl. to Bradley Intl., returning Sun, Jun 14, priced at $147 found 12 hours ago
Avelo Airlines
Thu, Jun 11 - Mon, Jun 15
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$163 Roundtrip, found 5 hours ago
$163
Roundtrip
found 5 hours ago
Select Avelo Airlines flight, departing Thu, Jun 11 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Jun 15, priced at $163 found 5 hours ago
Frontier Airlines
Thu, Apr 16 - Fri, Apr 24
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$210 Roundtrip, found 3 days ago
$210
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Apr 16 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Fri, Apr 24, priced at $210 found 3 days ago
Delta
Tue, Jun 9 - Tue, Jun 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$227 Roundtrip, found 1 day ago
$227
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 9 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Tue, Jun 16, priced at $227 found 1 day ago
JetBlue Airways
Tue, Jun 9 - Mon, Jun 15
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Jun 9 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Jun 15, priced at $247 found 1 day ago
American Airlines
Tue, Apr 7 - Tue, Apr 14
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$275 Roundtrip, found 6 days ago
$275
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Apr 7 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Tue, Apr 14, priced at $275 found 6 days ago
United
Tue, Apr 14 - Mon, Apr 27
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$276 Roundtrip, found 2 days ago
$276
Roundtrip
found 2 days ago
Select United flight, departing Tue, Apr 14 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Apr 27, priced at $276 found 2 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 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 $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
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$106

Last Minute Hotel Deals in Cheshire

New Haven Hotel

New Haven Hotel

3.5 out of 5
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! (2,068 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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New Haven Hotel
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! (1,258 reviews)
breakfast was fine did not use a/c

Reviewed on Mar 31, 2026

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Holiday Inn Express Southington by IHG
The Capitol Hotel

The Capitol Hotel

3 out of 5
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! (1,227 reviews)
Staff seemed to be very nice and although they did not seem to know how their own parking service worked, they did try to help. No loud noises and slept like a baby. The beds comfortness seemed ot be right where i like it, nit so much for the other guest. Pillows definetly could use an upgrade. WOUldnt ...

Reviewed on Apr 6, 2026

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The Capitol Hotel
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
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! (1,293 reviews)
Outdated, felt like a renovated motel

Reviewed on Apr 4, 2026

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Hyatt Place Milford / New Haven
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
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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Omni New Haven Hotel at Yale
Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

2.5 out of 5
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! (1,143 reviews)
Staff was very friendly.

Reviewed on Apr 5, 2026

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Hampton Inn & Suites Hartford/East Hartford
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
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! (1,098 reviews)
clean rooms

Reviewed on Apr 6, 2026

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Hilton Garden Inn Shelton
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
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! (1,003 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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Motel 6 New Haven - Branford, CT
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.