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Cheshire

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Cheshire Flights as Low as $101

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

Frontier Airlines
Thu, Mar 20 - Wed, Mar 26
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$101 Roundtrip, found 4 days ago
$101
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Mar 20 from Dallas-Fort Worth Intl. to Bradley Intl., returning Wed, Mar 26, priced at $101 found 4 days ago
Frontier Airlines
Tue, Mar 4 - Mon, Mar 10
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$120 Roundtrip, found 4 days ago
$120
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Mar 4 from Dallas-Fort Worth Intl. to Bradley Intl., returning Mon, Mar 10, priced at $120 found 4 days ago
Frontier Airlines
Tue, Mar 4 - Sat, Mar 8
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$135 Roundtrip, found 4 days ago
$135
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Mar 4 from Dallas-Fort Worth Intl. to Bradley Intl., returning Sat, Mar 8, priced at $135 found 4 days ago
Frontier Airlines
Thu, Apr 3 - Sat, Apr 5
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$140 Roundtrip, found 6 days ago
$140
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Apr 3 from Dallas-Fort Worth Intl. to Bradley Intl., returning Sat, Apr 5, priced at $140 found 6 days ago
Frontier Airlines
Tue, Mar 4 - Sun, Mar 9
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$146 Roundtrip, found 4 days ago
$146
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Mar 4 from Dallas-Fort Worth Intl. to Bradley Intl., returning Sun, Mar 9, priced at $146 found 4 days ago
Frontier Airlines
Thu, Apr 3 - Mon, Apr 7
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$156 Roundtrip, found 6 days ago
$156
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Apr 3 from Dallas-Fort Worth Intl. to Bradley Intl., returning Mon, Apr 7, priced at $156 found 6 days ago
Frontier Airlines
Fri, Mar 7 - Sat, Mar 8
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$162 Roundtrip, found 4 days ago
$162
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Mar 7 from Dallas-Fort Worth Intl. to Bradley Intl., returning Sat, Mar 8, priced at $162 found 4 days ago
Frontier Airlines
Fri, Mar 7 - Sun, Mar 9
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$173 Roundtrip, found 4 days ago
$173
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Mar 7 from Dallas-Fort Worth Intl. to Bradley Intl., returning Sun, Mar 9, priced at $173 found 4 days ago
Spirit Airlines
Wed, Mar 5 - Sat, Mar 8
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$179 Roundtrip, found 4 days ago
$179
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Mar 5 from Dallas-Fort Worth Intl. to Bradley Intl., returning Sat, Mar 8, priced at $179 found 4 days ago
Frontier Airlines
Fri, Apr 4 - Sat, Apr 5
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$179 Roundtrip, found 6 days ago
$179
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, Apr 4 from Dallas-Fort Worth Intl. to Bradley Intl., returning Sat, Apr 5, priced at $179 found 6 days ago
Spirit Airlines
Wed, Mar 5 - Mon, Mar 10
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$187 Roundtrip, found 4 days ago
$187
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Mar 5 from Dallas-Fort Worth Intl. to Bradley Intl., returning Mon, Mar 10, priced at $187 found 4 days ago
Frontier Airlines
Fri, Apr 4 - Mon, Apr 7
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$191 Roundtrip, found 6 days ago
$191
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, Apr 4 from Dallas-Fort Worth Intl. to Bradley Intl., returning Mon, Apr 7, priced at $191 found 6 days ago
American Airlines
Thu, Mar 20 - Wed, Mar 26
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$199 Roundtrip, found 4 days ago
$199
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Mar 20 from Dallas-Fort Worth Intl. to Bradley Intl., returning Wed, Mar 26, priced at $199 found 4 days ago
Delta
Wed, May 14 - Sat, May 17
DAL
Love Field
BDL
Bradley Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, May 14 from Love Field to Bradley Intl., returning Sat, May 17, priced at $237 found 1 day ago
United
Thu, Apr 3 - Mon, Apr 7
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$297 Roundtrip, found 6 days ago
$297
Roundtrip
found 6 days ago
Select United flight, departing Thu, Apr 3 from Dallas-Fort Worth Intl. to Bradley Intl., returning Mon, Apr 7, priced at $297 found 6 days ago
Spirit Airlines
Wed, Feb 26 - Tue, Mar 4
DTW
Detroit Metropolitan Wayne County
BDL
Bradley Intl.
$312 Roundtrip, found 1 day ago
$312
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Feb 26 from Detroit Metropolitan Wayne County to Bradley Intl., returning Tue, Mar 4, priced at $312 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 March, 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 $101, 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 $101 right now, why wait?

Cheshire Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$101

Last Minute Hotel Deals in Cheshire

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 $104 per night from Mar 9 to Mar 10
$104
includes taxes & fees
Mar 9 - Mar 10
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! (1,002 reviews)
"Not much"

Reviewed on Feb 18, 2025

Holiday Inn Cheshire - Southington, an IHG Hotel
New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
The price is $136 per night from Mar 2 to Mar 3
$136
includes taxes & fees
Mar 2 - Mar 3
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! (1,462 reviews)
"Hotels in this area are expensive for their worth."

Reviewed on Feb 20, 2025

New Haven Hotel
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 Mar 8 to Mar 9
$174
includes taxes & fees
Mar 8 - Mar 9
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 ...
8/10 Very Good! (1,003 reviews)
"Had a great stay. Staff very welcoming."

Reviewed on Feb 20, 2025

Omni New Haven Hotel at Yale
The Capitol Hotel, Ascend Hotel Collection
The Capitol Hotel, Ascend Hotel Collection
3 out of 5
440 Asylum St, Hartford, CT
The price is $104 per night from Feb 26 to Feb 27
$104
includes taxes & fees
Feb 26 - Feb 27
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 ...
7.2/10 Good! (1,001 reviews)
"I wish I got the front end lady name but she was quick a super nice. The rooms were clean and warm upon arrival."

Reviewed on Feb 11, 2025

The Capitol Hotel, Ascend Hotel Collection
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 $126 per night from Mar 9 to Mar 10
$126
includes taxes & fees
Mar 9 - Mar 10
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 ...
8.8/10 Excellent! (634 reviews)
"Very classy hotel and very clean"

Reviewed on Feb 11, 2025

Cambria Hotel New Haven University Area
Hampton Inn & Suites Hartford/East Hartford
Hampton Inn & Suites Hartford/East Hartford
2.5 out of 5
351 Pitkin Steet, East Hartford, CT
The price is $118 per night from Mar 2 to Mar 3
$118
includes taxes & fees
Mar 2 - Mar 3
Stay at this hotel in East Hartford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9/10 Wonderful! (1,005 reviews)
Staff needs training in customer services
"Hotel was beautiful, and the view was nice but hotel staff have an iffy attitude. I asked for a fan during my stay and the lady laughed over the phone and’s made snark remarks and brought it up all dusty and handed it over rudely."

Reviewed on Feb 20, 2025

Hampton Inn & Suites Hartford/East Hartford
Hyatt House Shelton
Hyatt House Shelton
3 out of 5
830 Bridgeport Ave, Shelton, CT
The price is $127 per night from Mar 2 to Mar 3
$127
includes taxes & fees
Mar 2 - Mar 3
Stay at this 3-star business-friendly hotel in Shelton. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
8.4/10 Very Good! (1,007 reviews)
"Our stay was good. Would really like to have seen the hot tub open."

Reviewed on Feb 21, 2025

Hyatt House Shelton
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
The price is $100 per night from Mar 9 to Mar 10
$100
includes taxes & fees
Mar 9 - Mar 10
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 ...
7.6/10 Good! (1,007 reviews)
"No plug ins for phones. One electrical outlet by the bed but it was worn out and the plug would just fall out when you tried to plug into it"

Reviewed on Feb 19, 2025

Best Western Executive Hotel Of New Haven - West Haven
See all 1,121 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.