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Cheshire

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Cheshire Flights as Low as $80

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

Frontier Airlines
Fri, May 1 - Sun, May 3
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$80 Roundtrip, found 1 hour ago
$80
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, May 1 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Sun, May 3, priced at $80 found 1 hour ago
Frontier Airlines
Fri, May 29 - Fri, Jun 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$103 Roundtrip, found 3 hours ago
$103
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, May 29 from Orlando Intl. to Bradley Intl., returning Fri, Jun 12, priced at $103 found 3 hours ago
Frontier Airlines
Fri, May 1 - Sat, May 16
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$110 Roundtrip, just found
$110
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, May 1 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Sat, May 16, priced at $110 just found
Frontier Airlines
Sat, May 9 - Sat, May 30
MCO
Orlando Intl.
BDL
Bradley Intl.
$113 Roundtrip, found 1 hour ago
$113
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, May 9 from Orlando Intl. to Bradley Intl., returning Sat, May 30, priced at $113 found 1 hour ago
Breeze Airways
Wed, May 20 - Fri, Jun 5
MCO
Orlando Intl.
BDL
Bradley Intl.
$114 Roundtrip, just found
$114
Roundtrip
just found
Select Breeze Airways flight, departing Wed, May 20 from Orlando Intl. to Bradley Intl., returning Fri, Jun 5, priced at $114 just found
Frontier Airlines
Thu, Apr 30 - Sat, May 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$116 Roundtrip, found 3 hours ago
$116
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Orlando Intl. to Bradley Intl., returning Sat, May 9, priced at $116 found 3 hours ago
Breeze Airways
Fri, May 15 - Sat, May 30
MCO
Orlando Intl.
BDL
Bradley Intl.
$117 Roundtrip, just found
$117
Roundtrip
just found
Select Breeze Airways flight, departing Fri, May 15 from Orlando Intl. to Bradley Intl., returning Sat, May 30, priced at $117 just found
Avelo Airlines
Thu, Apr 30 - Sat, May 9
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$140 Roundtrip, found 4 hours ago
$140
Roundtrip
found 4 hours ago
Select Avelo Airlines flight, departing Thu, Apr 30 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, May 9, priced at $140 found 4 hours ago
Breeze Airways
Tue, May 19 - Tue, Jun 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$151 Roundtrip, just found
$151
Roundtrip
just found
Select Breeze Airways flight, departing Tue, May 19 from Orlando Intl. to Bradley Intl., returning Tue, Jun 2, priced at $151 just found
Delta
Tue, May 5 - Tue, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$159 Roundtrip, found 1 hour ago
$159
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, May 5 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Tue, May 12, priced at $159 found 1 hour ago
Frontier Airlines
Thu, May 7 - Sat, May 9
TPA
Tampa Intl.
BDL
Bradley Intl.
$174 Roundtrip, found 1 hour ago
$174
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, May 7 from Tampa Intl. to Bradley Intl., returning Sat, May 9, priced at $174 found 1 hour ago
Frontier Airlines
Thu, Apr 16 - Thu, Apr 30
ORD
O'Hare Intl.
BDL
Bradley Intl.
$181 Roundtrip, just found
$181
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Apr 16 from O'Hare Intl. to Bradley Intl., returning Thu, Apr 30, priced at $181 just found
American Airlines
Tue, May 5 - Tue, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$187 Roundtrip, found 1 hour ago
$187
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, May 5 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Tue, May 12, priced at $187 found 1 hour ago
JetBlue Airways
Thu, May 7 - Sat, May 9
TPA
Tampa Intl.
BDL
Bradley Intl.
$187 Roundtrip, found 1 hour ago
$187
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Thu, May 7 from Tampa Intl. to Bradley Intl., returning Sat, May 9, priced at $187 found 1 hour ago
United
Sat, May 9 - Tue, May 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select United flight, departing Sat, May 9 from Orlando Intl. to Bradley Intl., returning Tue, May 12, priced at $217 found 1 hour ago
Avelo Airlines
Thu, Apr 16 - Mon, Apr 20
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$225 Roundtrip, found 2 days ago
$225
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Thu, Apr 16 from Tampa Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $225 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 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 $80, 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 $80 right now, why wait?

Cheshire Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$80

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! (2,069 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! (1,260 reviews)
Rooms were clean and staff was friendly. Complementary breakfast was ideal. Thank you.

Reviewed on Apr 6, 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! (1,294 reviews)
The breakfast is excellent. A lot of choices. The room is spacious and clean. The staff are nice.

Reviewed on Apr 6, 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)
the rooms do not have sound proof windows. some of the rooms, unfortunately our room, face the main street with bars, rowdy patrons, loud cars, and loud music. we got no sleep at all Friday night and Saturday night. we moved in to a different hotel for the last night our our stay. got zero sleep ...

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)
The room was mostly clean but the bed had some stains on it. There was paper on the floor...made me feel that they didnt really clean. Staff was pleasant though.

Reviewed on Apr 6, 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)
Quiet Clean Excellent food...5 stars all around.

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.