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Cheshire

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Cheshire Flights as Low as $98

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

Spirit Airlines
Fri, Sep 19 - Fri, Sep 26
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$98 Roundtrip, found 14 hours ago
$98
Roundtrip
found 14 hours ago
Select Spirit Airlines flight, departing Fri, Sep 19 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Fri, Sep 26, priced at $98 found 14 hours ago
Spirit Airlines
Sat, Aug 30 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$100 Roundtrip, found 6 hours ago
$100
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Sat, Aug 30 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $100 found 6 hours ago
Breeze Airways
Fri, Aug 1 - Mon, Aug 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$102 Roundtrip, found 4 hours ago
$102
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Bradley Intl., returning Mon, Aug 4, priced at $102 found 4 hours ago
Breeze Airways
Fri, Aug 1 - Mon, Aug 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$107 Roundtrip, found 4 hours ago
$107
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Bradley Intl., returning Mon, Aug 4, priced at $107 found 4 hours ago
Spirit Airlines
Fri, Jul 11 - Fri, Jul 18
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$108 Roundtrip, found 8 hours ago
$108
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Fri, Jul 11 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Fri, Jul 18, priced at $108 found 8 hours ago
Breeze Airways
Fri, Aug 1 - Mon, Aug 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$112 Roundtrip, found 4 hours ago
$112
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Bradley Intl., returning Mon, Aug 4, priced at $112 found 4 hours ago
Breeze Airways
Fri, Aug 1 - Mon, Aug 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$113 Roundtrip, found 4 hours ago
$113
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Bradley Intl., returning Mon, Aug 4, priced at $113 found 4 hours ago
Avelo Airlines
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$113 Roundtrip, found 10 hours ago
$113
Roundtrip
found 10 hours ago
Select Avelo Airlines flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $113 found 10 hours ago
Breeze Airways
Fri, Aug 1 - Mon, Aug 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$118 Roundtrip, found 4 hours ago
$118
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Bradley Intl., returning Mon, Aug 4, priced at $118 found 4 hours ago
Spirit Airlines
Sat, Aug 16 - Thu, Aug 21
MCO
Orlando Intl.
BDL
Bradley Intl.
$120 Roundtrip, found 23 hours ago
$120
Roundtrip
found 23 hours ago
Select Spirit Airlines flight, departing Sat, Aug 16 from Orlando Intl. to Bradley Intl., returning Thu, Aug 21, priced at $120 found 23 hours ago
Frontier Airlines
Sat, Aug 30 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$140 Roundtrip, found 6 hours ago
$140
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $140 found 6 hours ago
American Airlines
Sat, Aug 9 - Sat, Aug 23
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$157 Roundtrip, found 6 hours ago
$157
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sat, Aug 9 from Charlotte-Douglas Intl. to Bradley Intl., returning Sat, Aug 23, priced at $157 found 6 hours ago
JetBlue Airways
Sat, Aug 30 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$159 Roundtrip, found 6 hours ago
$159
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Sat, Aug 30 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $159 found 6 hours ago
United
Fri, Aug 15 - Thu, Aug 21
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$190 Roundtrip, found 6 hours ago
$190
Roundtrip
found 6 hours ago
Select United flight, departing Fri, Aug 15 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Thu, Aug 21, priced at $190 found 6 hours ago
Delta
Sat, Aug 9 - Sat, Aug 23
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$197 Roundtrip, found 6 hours ago
$197
Roundtrip
found 6 hours ago
Select Delta flight, departing Sat, Aug 9 from Charlotte-Douglas Intl. to Bradley Intl., returning Sat, Aug 23, priced at $197 found 6 hours ago
Avelo Airlines
Fri, Jun 27 - Sun, Jun 29
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$204 Roundtrip, found 2 days ago
$204
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Fri, Jun 27 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sun, Jun 29, priced at $204 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 September, 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 $98, 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 $98 right now, why wait?

Cheshire Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$100

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! (693 reviews)
"very clean. would stay again"

Reviewed on Jun 24, 2025

Get rates
Cheshire Welcome Inn
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! (1,001 reviews)
"Good"

Reviewed on Jun 22, 2025

Get rates
Holiday Inn Cheshire - Southington by IHG
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! (1,006 reviews)
"amazing value"

Reviewed on Jun 21, 2025

Get rates
The Capitol Hotel
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! (1,610 reviews)
"I really liked the New Haven Hotel. Greeted me with two free drinks. Next morning I went down to buy a Pepsi and was told just to take one. Fantastic location and great staff. Wish it had a restaurant, but otherwise perfect for my stay."

Reviewed on Jun 23, 2025

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New Haven Hotel
Hyatt Place Milford / New Haven
Hyatt Place Milford / New Haven
3 out of 5
190 Old Gate Lane, Milford, CT
Stay at this 3-star 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! (1,029 reviews)
"Very clean and the staff was so kind"

Reviewed on Jun 24, 2025

Get rates
Hyatt Place Milford / New Haven
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! (1,005 reviews)
"Check in was a breeze, staff was very accommodating, my room was clean and bed was comfy. Housekeeping came in and replaced towels, soap, etc. quiet room. It was great for the price."

Reviewed on Jun 22, 2025

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Clarion Inn
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! (1,011 reviews)
"Close to downtown"

Reviewed on Jun 22, 2025

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Hampton Inn & Suites Hartford/East Hartford
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 (1,015 reviews)
Overall very good hotel
"The stay was good. It was clean, staff very friendly. The only thing we didn't like, The elevatores were down it was very enconvenience. And my room The TV was rented not working i reported they said it will take a few minutes then i call again they said it was the weekend they had no one to look ..."

Reviewed on Jun 21, 2025

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La Quinta Inn & Suites by Wyndham New Haven
See all 1,148 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.