Search Cheap Flights to
Cheshire

Photo by Tai Bui

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Cheshire Flights as Low as $207

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

American Airlines
Thu, May 29 - Sat, May 31
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$207 Roundtrip, found 4 hours ago
$207
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Thu, May 29 from Dallas-Fort Worth Intl. to Bradley Intl., returning Sat, May 31, priced at $207 found 4 hours ago
Spirit Airlines
Sat, May 31 - Sun, Jun 8
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$214 Roundtrip, found 6 days ago
$214
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Sat, May 31 from Luis Munoz Marin Intl. to Bradley Intl., returning Sun, Jun 8, priced at $214 found 6 days ago
Delta
Sat, Jun 14 - Wed, Jun 18
CAE
Columbia Metropolitan
BDL
Bradley Intl.
$217 Roundtrip, found 20 hours ago
$217
Roundtrip
found 20 hours ago
Select Delta flight, departing Sat, Jun 14 from Columbia Metropolitan to Bradley Intl., returning Wed, Jun 18, priced at $217 found 20 hours ago
Delta
Wed, Jun 11 - Tue, Jun 17
CAE
Columbia Metropolitan
BDL
Bradley Intl.
$220 Roundtrip, found 20 hours ago
$220
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Jun 11 from Columbia Metropolitan to Bradley Intl., returning Tue, Jun 17, priced at $220 found 20 hours ago
Frontier Airlines
Thu, May 15 - Sat, May 17
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$222 Roundtrip, found 6 days ago
$222
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, May 15 from Dallas-Fort Worth Intl. to Bradley Intl., returning Sat, May 17, priced at $222 found 6 days ago
Spirit Airlines
Thu, May 29 - Sun, Jun 8
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$224 Roundtrip, found 1 day ago
$224
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, May 29 from Luis Munoz Marin Intl. to Bradley Intl., returning Sun, Jun 8, priced at $224 found 1 day ago
Frontier Airlines
Sat, Aug 9 - Mon, Aug 18
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$226 Roundtrip, found 17 hours ago
$226
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sat, Aug 9 from Luis Munoz Marin Intl. to Bradley Intl., returning Mon, Aug 18, priced at $226 found 17 hours ago
Spirit Airlines
Thu, May 29 - Thu, Jun 5
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$229 Roundtrip, found 4 days ago
$229
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, May 29 from Luis Munoz Marin Intl. to Bradley Intl., returning Thu, Jun 5, priced at $229 found 4 days ago
Delta
Thu, May 29 - Sat, May 31
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$231 Roundtrip, found 4 hours ago
$231
Roundtrip
found 4 hours ago
Select Delta flight, departing Thu, May 29 from Dallas-Fort Worth Intl. to Bradley Intl., returning Sat, May 31, priced at $231 found 4 hours ago
Frontier Airlines
Thu, May 15 - Sun, May 25
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$231 Roundtrip, found 3 hours ago
$231
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, May 15 from Dallas-Fort Worth Intl. to Bradley Intl., returning Sun, May 25, priced at $231 found 3 hours ago
Delta
Sat, Jun 14 - Sun, Jun 15
CAE
Columbia Metropolitan
BDL
Bradley Intl.
$233 Roundtrip, found 20 hours ago
$233
Roundtrip
found 20 hours ago
Select Delta flight, departing Sat, Jun 14 from Columbia Metropolitan to Bradley Intl., returning Sun, Jun 15, priced at $233 found 20 hours ago
Spirit Airlines
Sat, May 10 - Sun, May 25
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$234 Roundtrip, found 1 day ago
$234
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, May 10 from Luis Munoz Marin Intl. to Bradley Intl., returning Sun, May 25, priced at $234 found 1 day ago
JetBlue Airways
Wed, Jun 4 - Sun, Jun 8
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$234 Roundtrip, found 6 days ago
$234
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Jun 4 from Luis Munoz Marin Intl. to Bradley Intl., returning Sun, Jun 8, priced at $234 found 6 days ago
Delta
Mon, Aug 11 - Thu, Aug 14
DAL
Love Field
BDL
Bradley Intl.
$237 Roundtrip, found 15 hours ago
$237
Roundtrip
found 15 hours ago
Select Delta flight, departing Mon, Aug 11 from Love Field to Bradley Intl., returning Thu, Aug 14, priced at $237 found 15 hours ago
JetBlue Airways
Thu, May 29 - Sun, Jun 1
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$256 Roundtrip, found 4 days ago
$256
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Thu, May 29 from Luis Munoz Marin Intl. to Bradley Intl., returning Sun, Jun 1, priced at $256 found 4 days ago
United
Mon, Aug 11 - Thu, Aug 14
DFW
Dallas-Fort Worth Intl.
BDL
Bradley Intl.
$312 Roundtrip, found 15 hours ago
$312
Roundtrip
found 15 hours ago
Select United flight, departing Mon, Aug 11 from Dallas-Fort Worth Intl. to Bradley Intl., returning Thu, Aug 14, priced at $312 found 15 hours 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 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 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 $207, 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 $207 right now, why wait?

Cheshire Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$206

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
The price is $121 per night from May 4 to May 5
$121
includes taxes & fees
May 4 - May 5
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)
"The hotel is a fantastic deal, it is clean, the staff was attentive and reasonably priced."

Reviewed on Apr 27, 2025

Holiday Inn Cheshire - Southington by IHG
Cheshire Welcome Inn
Cheshire Welcome Inn
2.5 out of 5
1106 S Main St., Cheshire, CT
The price is $125 per night from May 4 to May 5
$125
includes taxes & fees
May 4 - May 5
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! (663 reviews)
"Quiet, clean and convenient. Staff was very friendly and welcoming. I will definitely return."

Reviewed on Apr 27, 2025

Cheshire Welcome Inn
New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
The price is $146 per night from May 4 to May 5
$146
includes taxes & fees
May 4 - May 5
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! (1,509 reviews)
"Nice convenient hotel if you are visiting Yale University. The hotel parking is $24/day which was taken out from safety deposit."

Reviewed on Apr 29, 2025

New Haven 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 $146 per night from May 4 to May 5
$146
includes taxes & fees
May 4 - May 5
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! (712 reviews)
"The hotel is very clean and in a quiet area. Will stay in here again if I come to New Haven."

Reviewed on Apr 28, 2025

Cambria Hotel New Haven University Area
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
The price is $108 per night from May 7 to May 8
$108
includes taxes & fees
May 7 - May 8
Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.4/10 Good! (1,007 reviews)
"Excellent customer service"

Reviewed on Apr 22, 2025

Clarion Inn
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 $165 per night from May 14 to May 15
$165
includes taxes & fees
May 14 - May 15
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! (1,003 reviews)
"I had a wonderful stay at the Omni. All the staff were friendly and helpful. Anytime I had a challenge"

Reviewed on Apr 29, 2025

Omni New Haven Hotel at Yale
Hyatt Place Milford / New Haven
Hyatt Place Milford / New Haven
3 out of 5
190 Old Gate Lane, Milford, CT
The price is $137 per night from May 8 to May 9
$137
includes taxes & fees
May 8 - May 9
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! (1,005 reviews)
"It was a nice room."

Reviewed on Apr 25, 2025

Hyatt Place Milford / New Haven
Holiday Inn Express Southington by IHG
Holiday Inn Express Southington by IHG
2.5 out of 5
120 Laning St, Southington, CT
The price is $117 per night from May 4 to May 5
$117
includes taxes & fees
May 4 - May 5
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! (1,001 reviews)
One Night Turned Into Four
"I stayed at this location with my son the night before a conference in downtown Hartford. The hotel was well kept and staff were welcoming. We had anticipated on staying at another hotel downtown for the rest of our stay but unfortunately did not feel safe in that neighborhood. We immediately returned ..."

Reviewed on Apr 29, 2025

Holiday Inn Express Southington by IHG
See all 1,142 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.