Search Cheap Flights to
Cheshire

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

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
Bradley Intl.
Destination airport IATA code
BDL
Airlines serving
Alaska Airlines, American Airlines, Delta, United
Number of airlines serving
4
Roundtrip price
$433
Popular airline
United

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! (750 reviews)
It's a cute little motel near my son's house. We like the convenience and the price. The one negative is when you walk into the room it reeks of cleaning products. It's so strong I was sneezing for the first 15 mins. You get use to it but it never goes away.

Reviewed on Nov 2, 2025

Cheshire Welcome Inn
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! (1,145 reviews)
Room was immaculate; the staff was friendly and prompt Breakfast area neatly arranged. Will go back for sure

Reviewed on Oct 29, 2025

Holiday Inn Express 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! (1,075 reviews)
Yes

Reviewed on Nov 3, 2025

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! (1,004 reviews)
Great staff, very clean room

Reviewed on Oct 29, 2025

Best Western Hartford Hotel & Suites
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, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff ...
9/10 Wonderful! (1,877 reviews)
Room was clean, hotel staff were friendly, gym was excellent.

Reviewed on Nov 1, 2025

New Haven Hotel
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! (1,014 reviews)
We didnt get a chance to enjoy breakfast. Staff was great. Nice Hotel. One suggestion...handicap rooms should be a little more accessible. Walking down stairs, even (3) stairs, is a challenge.

Reviewed on Nov 3, 2025

Wyndham Southbury
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street, New Haven, CT
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
8.6/10 Excellent! (955 reviews)
Clean room quiet and nice staff

Reviewed on Nov 3, 2025

Cambria Hotel New Haven University Area
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. ...
6.8/10 (1,031 reviews)
Good

Reviewed on Oct 31, 2025

Motel 6 Wethersfield, CT - Hartford
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.