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Cheshire

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Cheshire Flights as Low as $145

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

American Airlines
Tue, Oct 21 - Sat, Oct 25
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$145 Roundtrip, found 2 days ago
$145
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Oct 21 from Charlotte-Douglas Intl. to Bradley Intl., returning Sat, Oct 25, priced at $145 found 2 days ago
American Airlines
Tue, Oct 21 - Sat, Oct 25
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$170 Roundtrip, found 2 days ago
$170
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Oct 21 from Charlotte-Douglas Intl. to Bradley Intl., returning Sat, Oct 25, priced at $170 found 2 days ago
American Airlines
Tue, Oct 21 - Sat, Oct 25
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$185 Roundtrip, found 2 days ago
$185
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Oct 21 from Charlotte-Douglas Intl. to Bradley Intl., returning Sat, Oct 25, priced at $185 found 2 days ago
Spirit Airlines
Mon, Sep 15 - Mon, Sep 22
IAH
George Bush Intercontinental
BDL
Bradley Intl.
$193 Roundtrip, found 5 days ago
$193
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Mon, Sep 15 from George Bush Intercontinental to Bradley Intl., returning Mon, Sep 22, priced at $193 found 5 days ago
American Airlines
Tue, Oct 21 - Sat, Oct 25
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$195 Roundtrip, found 2 days ago
$195
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Oct 21 from Charlotte-Douglas Intl. to Bradley Intl., returning Sat, Oct 25, priced at $195 found 2 days ago
Delta
Wed, Oct 22 - Sat, Oct 25
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Oct 22 from Charlotte-Douglas Intl. to Bradley Intl., returning Sat, Oct 25, priced at $197 found 2 days ago
Spirit Airlines
Wed, Sep 3 - Mon, Sep 8
IAH
George Bush Intercontinental
BDL
Bradley Intl.
$198 Roundtrip, found 3 days ago
$198
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Sep 3 from George Bush Intercontinental to Bradley Intl., returning Mon, Sep 8, priced at $198 found 3 days ago
Delta
Tue, Sep 16 - Sat, Sep 20
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$200 Roundtrip, found 10 hours ago
$200
Roundtrip
found 10 hours ago
Select Delta flight, departing Tue, Sep 16 from Charlotte-Douglas Intl. to Bradley Intl., returning Sat, Sep 20, priced at $200 found 10 hours ago
Bargain Flight
Tue, Aug 12 - Sat, Aug 23
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Aug 12 from Charlotte-Douglas Intl. to Bradley Intl., returning Sat, Aug 23, priced at $200 found 1 day ago
Spirit Airlines
Sat, Aug 30 - Mon, Sep 8
IAH
George Bush Intercontinental
BDL
Bradley Intl.
$200 Roundtrip, found 3 days ago
$200
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sat, Aug 30 from George Bush Intercontinental to Bradley Intl., returning Mon, Sep 8, priced at $200 found 3 days ago
Spirit Airlines
Thu, Sep 4 - Mon, Sep 8
IAH
George Bush Intercontinental
BDL
Bradley Intl.
$202 Roundtrip, found 3 days ago
$202
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, Sep 4 from George Bush Intercontinental to Bradley Intl., returning Mon, Sep 8, priced at $202 found 3 days ago
American Airlines
Tue, Oct 21 - Sat, Oct 25
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$205 Roundtrip, found 2 days ago
$205
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Oct 21 from Charlotte-Douglas Intl. to Bradley Intl., returning Sat, Oct 25, priced at $205 found 2 days ago
Spirit Airlines
Wed, Sep 3 - Fri, Sep 12
IAH
George Bush Intercontinental
BDL
Bradley Intl.
$208 Roundtrip, found 3 days ago
$208
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Sep 3 from George Bush Intercontinental to Bradley Intl., returning Fri, Sep 12, priced at $208 found 3 days ago
Spirit Airlines
Sat, Aug 30 - Fri, Sep 12
IAH
George Bush Intercontinental
BDL
Bradley Intl.
$210 Roundtrip, found 3 days ago
$210
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sat, Aug 30 from George Bush Intercontinental to Bradley Intl., returning Fri, Sep 12, priced at $210 found 3 days ago
Frontier Airlines
Mon, Aug 4 - Sat, Aug 9
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$221 Roundtrip, found 1 day ago
$221
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Aug 4 from Charlotte-Douglas Intl. to Bradley Intl., returning Sat, Aug 9, priced at $221 found 1 day ago
American Airlines
Tue, Sep 2 - Tue, Sep 9
HOU
William P. Hobby
BDL
Bradley Intl.
$228 Roundtrip, found 3 days ago
$228
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 2 from William P. Hobby to Bradley Intl., returning Tue, Sep 9, priced at $228 found 3 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 October, 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 $145, 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 $145 right now, why wait?

Cheshire Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$92

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
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! (1,000 reviews)
"Hotel staff was kind and hotel was"

Reviewed on Jul 22, 2025

Get rates
Holiday Inn Cheshire - Southington by IHG
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! (711 reviews)
"Good economy level stay. It was clean, well lit and comfortable."

Reviewed on Jul 27, 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! (1,049 reviews)
"Each stuff member was very friendly"

Reviewed on Jul 30, 2025

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The Capitol Hotel
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! (827 reviews)
"The staff was very nice and accommodating. Parking on site was very easy and nice, though the cost seemed a little high. The hotel is walkable distance to a lot of the things we wanted to do / see and the restaurants we wanted to eat at."

Reviewed on Jul 26, 2025

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Cambria Hotel New Haven University Area
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! (1,695 reviews)
"Right in the middle of downtown"

Reviewed on Jul 29, 2025

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New Haven Hotel
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd, West Haven, CT
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.8/10 Good! (1,239 reviews)
"Large clean property located in a convenient area"

Reviewed on Jul 30, 2025

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Best Western Executive Hotel Of New Haven - West Haven
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 ...
8.2/10 Very Good! (1,018 reviews)
"The hotel was nice. But the surrounding area outside of the hotel was a little sketchy."

Reviewed on Jul 26, 2025

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Omni New Haven Hotel at Yale
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St, Branford, CT
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 (1,023 reviews)
"It was good."

Reviewed on Jul 28, 2025

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Motel 6 New Haven - Branford, CT
See all 1,145 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.