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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.

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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.

Just the right flight

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.

Frequently Asked Questions About flights to Cheshire

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 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 $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?

Can I fly to Cheshire right now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to  right now?” When it’s time to book your flight, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

Cheshire Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$88

Last Minute Hotel Deals in Cheshire

Courtyard by Marriott Waterbury Downtown
Courtyard by Marriott Waterbury Downtown
3 out of 5
63 Grand St, Waterbury, CT
The price is $89 per night from Apr 21 to Apr 22
$89
per night
Apr 21 - Apr 22
Stay at this hotel in Waterbury. Enjoy free WiFi, breakfast, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8.2/10 Very Good! (1,003 reviews)
"It was great"

Reviewed on Apr 19, 2024

Courtyard by Marriott Waterbury Downtown
Holiday Inn Cheshire - Southington, an IHG Hotel
Holiday Inn Cheshire - Southington, an IHG Hotel
3 out of 5
64 Knotter Dr, Cheshire, CT
The price is $105 per night from Apr 22 to Apr 23
$105
per night
Apr 22 - Apr 23
Stay at this business-friendly hotel in Cheshire. Enjoy free WiFi, free parking, and breakfast. Our guests praise the helpful staff and the clean rooms in our ...
8.2/10 Very Good! (846 reviews)
"Very clean hotel. Beds very comfortable. Friendly staff. Will definitely return."

Reviewed on Apr 1, 2024

Holiday Inn Cheshire - Southington, an IHG Hotel
Cheshire Welcome Inn
Cheshire Welcome Inn
2.5 out of 5
1106 S Main St., Cheshire, CT
The price is $98 per night from Apr 22 to Apr 23
$98
per night
Apr 22 - Apr 23
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 convenient parking in our ...
8.4/10 Very Good! (549 reviews)
"We only stayed 1 night, the check in was easy it took less than 5 minutes. We arrived a few hours prior to stated check in time and they checked s in and gave us key to our room no questions asked. The room is large with a small attached room with counter, chair, and coffe maker. There is a Sushi ..."

Reviewed on Apr 14, 2024

Cheshire Welcome Inn
New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
The price is $169 per night from Apr 21 to Apr 22
$169
per night
Apr 21 - Apr 22
Stay at this business-friendly hotel in New Haven. Enjoy free WiFi, a fitness center, and onsite parking. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (1,217 reviews)
"A little old"

Reviewed on Apr 17, 2024

New Haven Hotel
Best Western Hartford Hotel & Suites
Best Western Hartford Hotel & Suites
2.5 out of 5
185 Brainard Rd, Hartford, CT
The price is $101 per night from Apr 28 to Apr 29
$101
per night
Apr 28 - Apr 29
Stay at this hotel in Hartford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions XL Center ...
7.8/10 Good! (1,000 reviews)
"I really enjoyed the staff snd their welcoming spirits. Very friendly and helpful."

Reviewed on Apr 12, 2024

Best Western Hartford Hotel & Suites
Hilton Garden Inn Shelton
Hilton Garden Inn Shelton
3 out of 5
25 Old Stratford Rd, Shelton, CT
The price is $110 per night from May 5 to May 6
$110
per night
May 5 - May 6
Stay at this 3-star business-friendly hotel in Shelton. Enjoy free WiFi, free parking, and breakfast. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (1,002 reviews)
"Is okay very good."

Reviewed on Apr 17, 2024

Hilton Garden Inn Shelton
Holiday Inn Express Southington, an IHG Hotel
Holiday Inn Express Southington, an IHG Hotel
2.5 out of 5
120 Laning St, Southington, CT
The price is $121 per night from Apr 28 to Apr 29
$121
per night
Apr 28 - Apr 29
Stay at this business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (983 reviews)
"Enjoy my stay and breakfast was fine"

Reviewed on Apr 18, 2024

Holiday Inn Express Southington, an IHG Hotel
Cambria Hotel New Haven University Area
Cambria Hotel New Haven University Area
3 out of 5
20 Dwight Street, New Haven, CT
The price is $144 per night from Apr 29 to Apr 30
$144
per night
Apr 29 - Apr 30
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free WiFi, breakfast, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (303 reviews)
"Awesome stay"

Reviewed on Apr 19, 2024

Cambria Hotel New Haven University Area
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.