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Cheshire

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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.

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 , 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  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 , 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  right now, why wait?

Cheshire Flight Information
Destination airport
Cheshire
Destination airport IATA code
BDL

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! (744 reviews)
"Clean comfortable room. Easy check in and out. Good location."

Reviewed on Oct 14, 2025

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Cheshire Welcome 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! (1,018 reviews)
"Beautiful view of the state capitol bldg. Room was clean and spacious. Room door did not shut fully by itself - had to push/pull to ensure closure. Main treadmill in fitness room not working. Could not access fitness room until 7am since on the same floor as breakfast space which opened at 7am. However, ..."

Reviewed on Oct 10, 2025

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The Capitol Hotel
Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

2.5 out of 5
185 Brainard Rd, Hartford, CT
Stay at this hotel in Hartford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
7.6/10 Good! (1,013 reviews)
"Excellent hospitality"

Reviewed on Oct 9, 2025

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Best Western Hartford Hotel & Suites
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St, New Haven, CT
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 ...
8.4/10 Very Good! (1,009 reviews)
"Super clean, friendly staff, fast elevators and easy parking. A no brainer for staying in New Haven."

Reviewed on Oct 7, 2025

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Omni New Haven Hotel at Yale
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 ...
9/10 Wonderful! (1,827 reviews)
"Friendly staff, easy parking"

Reviewed on Oct 11, 2025

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New Haven Hotel
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! (1,113 reviews)
"Safe"

Reviewed on Oct 9, 2025

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Holiday Inn Express Southington by IHG
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! (1,156 reviews)
"Staff are super nice. Rooms are clean but a little outdated! Biggest complaint is the distribution center? next door- those trucks get to work around 4:30am. I put the fan on to drown out the noise."

Reviewed on Oct 10, 2025

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Hyatt Place Milford / New Haven
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road, Southbury, CT
Stay at this 3-star business-friendly hotel in Southbury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8/10 Very Good! (1,019 reviews)
"This was a convenient stay for us while visiting family in the area, and a good value compared to others in the area. Happy that they had laundry facilities. Complimentary coffee was not half bad! Bathroom is small. Fitness room has no WiFi or cell signal. Both of those are minor things though. Staff ..."

Reviewed on Oct 10, 2025

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Wyndham Southbury
See all 1,135 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.