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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
Thu, Apr 24 - Sun, Apr 27
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Apr 24 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Sun, Apr 27, priced at $98 found 1 day ago
Spirit Airlines
Mon, Apr 14 - Tue, Apr 15
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$99 Roundtrip, found 1 day ago
$99
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Apr 14 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Tue, Apr 15, priced at $99 found 1 day ago
Spirit Airlines
Sun, Apr 13 - Tue, Apr 15
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Apr 13 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Tue, Apr 15, priced at $119 found 1 day ago
Spirit Airlines
Wed, Apr 23 - Sun, Apr 27
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$123 Roundtrip, found 1 day ago
$123
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Apr 23 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Sun, Apr 27, priced at $123 found 1 day ago
Spirit Airlines
Mon, Apr 14 - Sat, Apr 19
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$124 Roundtrip, found 1 day ago
$124
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Apr 14 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Sat, Apr 19, priced at $124 found 1 day ago
Spirit Airlines
Fri, Mar 28 - Wed, Apr 2
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$128 Roundtrip, found 1 day ago
$128
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, Mar 28 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Wed, Apr 2, priced at $128 found 1 day ago
Spirit Airlines
Fri, Apr 11 - Sun, Apr 20
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, Apr 11 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Sun, Apr 20, priced at $138 found 1 day ago
Spirit Airlines
Tue, Apr 22 - Sun, Apr 27
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Apr 22 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Sun, Apr 27, priced at $139 found 1 day ago
Spirit Airlines
Fri, Mar 28 - Mon, Mar 31
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$143 Roundtrip, found 1 day ago
$143
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, Mar 28 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Mar 31, priced at $143 found 1 day ago
Spirit Airlines
Sat, Mar 29 - Mon, Mar 31
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$144 Roundtrip, found 1 day ago
$144
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Mar 29 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Mar 31, priced at $144 found 1 day ago
Frontier Airlines
Tue, Jun 24 - Sat, Jun 28
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jun 24 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Sat, Jun 28, priced at $158 found 1 day ago
Delta
Wed, Apr 23 - Wed, Apr 23
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Apr 23 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Wed, Apr 23, priced at $217 found 1 day ago
American Airlines
Wed, Apr 9 - Wed, Apr 9
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$248 Roundtrip, found 1 day ago
$248
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Apr 9 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Wed, Apr 9, priced at $248 found 1 day ago
Frontier Airlines
Thu, Apr 3 - Tue, Apr 8
ORD
O'Hare Intl.
BDL
Bradley Intl.
$248 Roundtrip, found 3 hours ago
$248
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Apr 3 from O'Hare Intl. to Bradley Intl., returning Tue, Apr 8, priced at $248 found 3 hours ago
JetBlue Airways
Thu, Mar 27 - Mon, Mar 31
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$253 Roundtrip, found 1 day ago
$253
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Mar 27 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Mar 31, priced at $253 found 1 day ago
United
Fri, Mar 28 - Tue, Apr 1
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$284 Roundtrip, found 1 day ago
$284
Roundtrip
found 1 day ago
Select United flight, departing Fri, Mar 28 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Tue, Apr 1, priced at $284 found 1 day 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 $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
$98

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
The price is $120 per night from Mar 30 to Mar 31
$120
includes taxes & fees
Mar 30 - Mar 31
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! (1,003 reviews)
"La propiedad bien limpia, la comida estaba buena, lo único es que no había nadie que hablara español"

Reviewed on Mar 21, 2025

Holiday Inn Cheshire - Southington by IHG
Cheshire Welcome Inn
Cheshire Welcome Inn
2.5 out of 5
1106 S Main St., Cheshire, CT
The price is $91 per night from Mar 26 to Mar 27
$91
includes taxes & fees
Mar 26 - Mar 27
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! (655 reviews)
"I liked it"

Reviewed on Mar 10, 2025

Cheshire Welcome Inn
New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
The price is $136 per night from Apr 6 to Apr 7
$136
includes taxes & fees
Apr 6 - Apr 7
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! (1,472 reviews)
"Perfect Stay – Excellent Location & Excellent Service I had a fantastic stay at this hotel! The location couldn’t be better—everything was easily accessible, making it convenient for exploring the area. The customer service was excellent; the staff was warm, attentive, and always ready to assist. ..."

Reviewed on Mar 20, 2025

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
The price is $79 per night from Mar 30 to Mar 31
$79
includes taxes & fees
Mar 30 - Mar 31
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. ...
6.8/10 (1,011 reviews)
"Very nice and staff friendly"

Reviewed on Mar 2, 2025

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
The price is $109 per night from Mar 30 to Mar 31
$109
includes taxes & fees
Mar 30 - Mar 31
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! (1,009 reviews)
"Very nice property and very nice people"

Reviewed on Mar 22, 2025

Holiday Inn Express Southington by IHG
Omni New Haven Hotel at Yale
Omni New Haven Hotel at Yale
4 out of 5
155 Temple St, New Haven, CT
The price is $174 per night from Apr 13 to Apr 14
$174
includes taxes & fees
Apr 13 - Apr 14
Stay at this 4-star business-friendly hotel in New Haven. Enjoy 2 restaurants, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,005 reviews)
"The amenities can be improved on; had to ask for hand lotion. The quality of the shampoo and conditioner and lotion is weak. Heater is noisy - system needs replacement. The staff were very kind and accommodating which made a big difference."

Reviewed on Mar 22, 2025

Omni New Haven Hotel at Yale
Hyatt Place Milford / New Haven
Hyatt Place Milford / New Haven
3 out of 5
190 Old Gate Lane, Milford, CT
The price is $137 per night from Apr 6 to Apr 7
$137
includes taxes & fees
Apr 6 - Apr 7
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! (1,006 reviews)
"Staff is amazing. They always make me feel welcome. The room cleaners do a great job and they’re trustworthy people. Love the Hyatt."

Reviewed on Mar 23, 2025

Hyatt Place Milford / New Haven
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
The price is $99 per night from Apr 6 to Apr 7
$99
includes taxes & fees
Apr 6 - Apr 7
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! (1,007 reviews)
"Nice hotel with free breakfast"

Reviewed on Mar 23, 2025

Clarion Inn
See all 1,140 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.