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Cheshire

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Cheshire Flights as Low as $153

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

Frontier Airlines
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$153 Roundtrip, found 4 hours ago
$153
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Wed, Sep 2, priced at $153 found 4 hours ago
Frontier Airlines
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$155 Roundtrip, found 4 hours ago
$155
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Wed, Sep 2, priced at $155 found 4 hours ago
Frontier Airlines
Sat, Jun 20 - Sat, Jul 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$164 Roundtrip, found 1 day ago
$164
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jun 20 from Orlando Intl. to Bradley Intl., returning Sat, Jul 4, priced at $164 found 1 day ago
Breeze Airways
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$166 Roundtrip, found 4 hours ago
$166
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Wed, Sep 2, priced at $166 found 4 hours ago
Breeze Airways
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$168 Roundtrip, found 4 hours ago
$168
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Wed, Sep 2, priced at $168 found 4 hours ago
Breeze Airways
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$171 Roundtrip, found 4 hours ago
$171
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Wed, Sep 2, priced at $171 found 4 hours ago
Frontier Airlines
Wed, Jun 17 - Sat, Jul 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$174 Roundtrip, found 1 day ago
$174
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Jun 17 from Orlando Intl. to Bradley Intl., returning Sat, Jul 4, priced at $174 found 1 day ago
United
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$229 Roundtrip, found 4 hours ago
$229
Roundtrip
found 4 hours ago
Select United flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Wed, Sep 2, priced at $229 found 4 hours ago
Delta
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$229 Roundtrip, found 4 hours ago
$229
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Wed, Sep 2, priced at $229 found 4 hours ago
JetBlue Airways
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$229 Roundtrip, found 4 hours ago
$229
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Wed, Sep 2, priced at $229 found 4 hours ago
Bargain Flight
Wed, Jul 29 - Wed, Aug 19
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$229 Roundtrip, found 4 hours ago
$229
Roundtrip
found 4 hours ago
Select Bargain Flight flight, departing Wed, Jul 29 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Wed, Aug 19, priced at $229 found 4 hours ago
American Airlines
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$247 Roundtrip, found 4 hours ago
$247
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Wed, Sep 2, priced at $247 found 4 hours ago
Breeze Airways
Wed, Jun 10 - Wed, Jun 10
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$254 Roundtrip, found 9 hours ago
$254
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Jun 10 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Jun 10, priced at $254 found 9 hours ago
Frontier Airlines
Thu, Jun 18 - Wed, Jun 24
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$266 Roundtrip, found 1 day ago
$266
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Jun 18 from Luis Munoz Marin Intl. to Bradley Intl., returning Wed, Jun 24, priced at $266 found 1 day ago
Avelo Airlines
Wed, Jun 10 - Sat, Jun 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$418 Roundtrip, just found
$418
Roundtrip
just found
Select Avelo Airlines flight, departing Wed, Jun 10 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Jun 13, priced at $418 just found
Avelo Airlines
Thu, Jun 18 - Sun, Jun 21
ATL
Hartsfield-Jackson Atlanta Intl.
HVN
Tweed - New Haven Regional
$456 Roundtrip, found 2 days ago
$456
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Thu, Jun 18 from Hartsfield-Jackson Atlanta Intl. to Tweed - New Haven Regional, returning Sun, Jun 21, priced at $456 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 August, 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 $153, 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 $153 right now, why wait?

Cheshire Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$153

Last Minute Hotel Deals in Cheshire

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! (822 reviews)
"Good"

Reviewed on Jun 1, 2026

Get rates
Cheshire Welcome Inn
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 ...
7.4/10 Good! (1,360 reviews)
"Mold in the bathroom and the tub wouldn’t drain. The beds and pillows were so uncomfortable. There were stains on the towels and the sheets. The room also smelled liked someone had been smoking and then tried to cover it up with cleaning products. The parking situation isnt great but also isnt the ..."

Reviewed on Jun 7, 2026

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The Capitol Hotel
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 ...
9.2/10 Wonderful! (2,165 reviews)
"It’s in a great location but is a bit long in the tooth for the money they charge per night. On the plus side there is garage parking right across the street that is included. The staff were very friendly. The rooms were a bit shoddy but ok."

Reviewed on Jun 6, 2026

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New Haven Hotel
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! (1,009 reviews)
"Cleaning and appearance could be better. For the price, it was OK."

Reviewed on Jun 7, 2026

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Motel 6 New Haven - Branford, CT
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! (1,324 reviews)
"My Daughter was sick on the bed and they were very fast getting the bedding changed out. The breakfast was very well maintained by attentive staff members and varied day to day. The 24 hrs coffee and hot chocolate was a great addition."

Reviewed on Jun 6, 2026

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Holiday Inn Express Southington by IHG
Motel 6 Wethersfield, CT - Hartford

Motel 6 Wethersfield, CT - Hartford

2 out of 5
1341 Silas Deane Hwy Wethersfield CT
Stay at this motel in Wethersfield. 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! (1,160 reviews)
"Reserved a queen with fridge and micro. Queen frame but not a queen mattress. Door to bathroom did not close or lock. Decent gap to entry door between frame and door itself. Have to unplug micro to use fridge. Samantha at front desk was busy but very polite and professional."

Reviewed on Jun 7, 2026

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Motel 6 Wethersfield, CT - Hartford
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! (1,023 reviews)
"Very nice place, conveniently situated to Yale."

Reviewed on Jun 3, 2026

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Omni New Haven Hotel at Yale
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd West Haven CT
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,645 reviews)
"Came here for one night, had multiple motorcyclists parked right outside our window in handicapped spots. The curtain doesn’t cover the whole window so I had to put something tall against it to hold it closed for privacy. It was beyond noisy. We came back from our evening event and there was no where ..."

Reviewed on Jun 7, 2026

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Best Western Executive Hotel Of New Haven - West Haven
See all 1,288 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.