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Cheshire

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Cheshire Flights as Low as $82

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

Breeze Airways
Wed, Jul 9 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$82 Roundtrip, found 2 days ago
$82
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Jul 9 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $82 found 2 days ago
Breeze Airways
Sat, Jun 14 - Tue, Jul 1
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$85 Roundtrip, found 1 day ago
$85
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Jun 14 from Orlando Intl. to Tweed - New Haven Regional, returning Tue, Jul 1, priced at $85 found 1 day ago
Breeze Airways
Wed, Jul 9 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$87 Roundtrip, found 2 days ago
$87
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Jul 9 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $87 found 2 days ago
Breeze Airways
Sat, Jun 14 - Tue, Jul 1
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$89 Roundtrip, found 1 day ago
$89
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Jun 14 from Orlando Intl. to Tweed - New Haven Regional, returning Tue, Jul 1, priced at $89 found 1 day ago
Avelo Airlines
Fri, Jun 13 - Mon, Jun 30
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Fri, Jun 13 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Jun 30, priced at $98 found 1 day ago
Breeze Airways
Sat, Jul 12 - Mon, Jul 14
MCO
Orlando Intl.
BDL
Bradley Intl.
$122 Roundtrip, found 1 day ago
$122
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Jul 12 from Orlando Intl. to Bradley Intl., returning Mon, Jul 14, priced at $122 found 1 day ago
Frontier Airlines
Sat, Jul 12 - Mon, Jul 14
MCO
Orlando Intl.
BDL
Bradley Intl.
$156 Roundtrip, found 1 day ago
$156
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jul 12 from Orlando Intl. to Bradley Intl., returning Mon, Jul 14, priced at $156 found 1 day ago
Frontier Airlines
Sat, Jun 21 - Sat, Jun 28
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$164 Roundtrip, found 3 days ago
$164
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Jun 21 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Sat, Jun 28, priced at $164 found 3 days ago
American Airlines
Wed, Jul 2 - Mon, Jul 7
PIT
Pittsburgh Intl.
BDL
Bradley Intl.
$167 Roundtrip, found 10 hours ago
$167
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Wed, Jul 2 from Pittsburgh Intl. to Bradley Intl., returning Mon, Jul 7, priced at $167 found 10 hours ago
Spirit Airlines
Sun, Jun 15 - Mon, Jun 16
MCO
Orlando Intl.
BDL
Bradley Intl.
$174 Roundtrip, found 2 days ago
$174
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sun, Jun 15 from Orlando Intl. to Bradley Intl., returning Mon, Jun 16, priced at $174 found 2 days ago
American Airlines
Wed, Jul 9 - Wed, Jul 16
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$189 Roundtrip, found 19 hours ago
$189
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Wed, Jul 9 from Dallas-Fort Worth Intl. to Bradley Intl., returning Wed, Jul 16, priced at $189 found 19 hours ago
Delta
Sat, Jul 5 - Tue, Jul 8
PIT
Pittsburgh Intl.
BDL
Bradley Intl.
$211 Roundtrip, found 10 hours ago
$211
Roundtrip
found 10 hours ago
Select Delta flight, departing Sat, Jul 5 from Pittsburgh Intl. to Bradley Intl., returning Tue, Jul 8, priced at $211 found 10 hours ago
United
Sat, Jun 7 - Sat, Jun 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$219 Roundtrip, found 3 days ago
$219
Roundtrip
found 3 days ago
Select United flight, departing Sat, Jun 7 from Orlando Intl. to Bradley Intl., returning Sat, Jun 7, priced at $219 found 3 days ago
Delta
Tue, Aug 12 - Sat, Aug 16
DAL
Love Field
BDL
Bradley Intl.
$237 Roundtrip, found 2 days ago
$237
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Aug 12 from Love Field to Bradley Intl., returning Sat, Aug 16, priced at $237 found 2 days ago
JetBlue Airways
Mon, Jun 30 - Sat, Jul 5
PIT
Pittsburgh Intl.
BDL
Bradley Intl.
$252 Roundtrip, found 10 hours ago
$252
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Mon, Jun 30 from Pittsburgh Intl. to Bradley Intl., returning Sat, Jul 5, priced at $252 found 10 hours ago
Avelo Airlines
Fri, Jun 6 - Sun, Jun 8
ATL
Hartsfield-Jackson Atlanta Intl.
HVN
Tweed - New Haven Regional
$280 Roundtrip, found 2 days ago
$280
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Fri, Jun 6 from Hartsfield-Jackson Atlanta Intl. to Tweed - New Haven Regional, returning Sun, Jun 8, priced at $280 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 July, 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 $82, 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 $82 right now, why wait?

Cheshire Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$81

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! (1,002 reviews)
"The breakfast was amazing, you had to order you breakfast which is better than a slip"

Reviewed on Jun 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! (681 reviews)
"Clean, friendly, helpful staff. Nice landscaping."

Reviewed on May 31, 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! (1,582 reviews)
"The staff was so accomodating.i had the room with the balcony. I was a solo traveler and i love to journal. This was perfect. Room was clean and everything is close by to walk to. Highly recommend. Will be back soon!"

Reviewed on Jun 2, 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! (1,006 reviews)
"The staff was extremely friendly and made sure our extremely large party was taken care of. We had an amazing time. However the room was dirty. There was a used soap on the dish, hair, dirt and mold in the tub an the water did not drain while showering. The place could use some maintenance and better ..."

Reviewed on May 31, 2025

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Clarion Inn
The Capitol Hotel
The Capitol Hotel
3 out of 5
440 Asylum St, Hartford, CT
Stay at this 3-star business-friendly hotel in Hartford. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
7.4/10 Good! (1,003 reviews)
"Great location and staff"

Reviewed on May 30, 2025

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The Capitol Hotel
La Quinta Inn & Suites by Wyndham New Haven
La Quinta Inn & Suites by Wyndham New Haven
3 out of 5
400 Sargent Dr, New Haven, CT
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
5.8/10 (1,009 reviews)
"Television did not work."

Reviewed on May 24, 2025

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La Quinta Inn & Suites by Wyndham New Haven
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! (1,006 reviews)
Good Stay
"Good Stay."

Reviewed on Jun 1, 2025

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Holiday Inn Express Southington by IHG
Courtyard by Marriott Waterbury Downtown
Courtyard by Marriott Waterbury Downtown
3 out of 5
63 Grand St, Waterbury, CT
Stay at this hotel in Waterbury. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (1,009 reviews)
NO BREAKFAST & PAID PARKING without advising it.
"Was never told breakfast was not included or any info about breakfast for that matter. Also was never told about $15 parking cost until I got the receipt iny email. Nice place, nice service but deceiving and that is too bad because I Won't be coming back again and I stay at hotels at least once a ..."

Reviewed on Jun 1, 2025

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Courtyard by Marriott Waterbury Downtown
See all 1,137 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.