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 $92

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

Spirit Airlines
Wed, Jun 18 - Wed, Jun 25
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$92 Roundtrip, found 1 day ago
$92
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Jun 18 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Wed, Jun 25, priced at $92 found 1 day ago
Breeze Airways
Fri, Aug 1 - Mon, Aug 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$97 Roundtrip, found 2 hours ago
$97
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Bradley Intl., returning Mon, Aug 4, priced at $97 found 2 hours ago
Breeze Airways
Fri, Aug 1 - Mon, Aug 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$102 Roundtrip, found 2 hours ago
$102
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Bradley Intl., returning Mon, Aug 4, priced at $102 found 2 hours ago
Spirit Airlines
Tue, Jun 24 - Sat, Jun 28
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$103 Roundtrip, found 3 days ago
$103
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Jun 24 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Sat, Jun 28, priced at $103 found 3 days ago
Breeze Airways
Fri, Aug 1 - Mon, Aug 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$107 Roundtrip, found 2 hours ago
$107
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Bradley Intl., returning Mon, Aug 4, priced at $107 found 2 hours ago
Spirit Airlines
Sat, Nov 15 - Mon, Nov 17
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$108 Roundtrip, found 2 hours ago
$108
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sat, Nov 15 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 17, priced at $108 found 2 hours ago
Breeze Airways
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$111 Roundtrip, found 3 days ago
$111
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $111 found 3 days ago
Breeze Airways
Fri, Jul 11 - Mon, Jul 14
TPA
Tampa Intl.
BDL
Bradley Intl.
$153 Roundtrip, found 1 day ago
$153
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jul 11 from Tampa Intl. to Bradley Intl., returning Mon, Jul 14, priced at $153 found 1 day ago
Avelo Airlines
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$153 Roundtrip, found 3 days ago
$153
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $153 found 3 days ago
Frontier Airlines
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$159 Roundtrip, found 4 hours ago
$159
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Fri, Sep 5 from Orlando Intl. to Bradley Intl., returning Sun, Sep 7, priced at $159 found 4 hours ago
JetBlue Airways
Wed, Nov 12 - Tue, Nov 18
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$167 Roundtrip, found 3 days ago
$167
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Nov 12 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Tue, Nov 18, priced at $167 found 3 days ago
American Airlines
Wed, Nov 12 - Wed, Nov 12
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$171 Roundtrip, found 2 days ago
$171
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Nov 12 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Wed, Nov 12, priced at $171 found 2 days ago
United
Fri, Aug 15 - Thu, Aug 21
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$187 Roundtrip, found 4 days ago
$187
Roundtrip
found 4 days ago
Select United flight, departing Fri, Aug 15 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Thu, Aug 21, priced at $187 found 4 days ago
Delta
Wed, Oct 1 - Tue, Oct 7
TPA
Tampa Intl.
BDL
Bradley Intl.
$217 Roundtrip, found 5 hours ago
$217
Roundtrip
found 5 hours ago
Select Delta flight, departing Wed, Oct 1 from Tampa Intl. to Bradley Intl., returning Tue, Oct 7, priced at $217 found 5 hours ago
Avelo Airlines
Fri, Jun 27 - Sun, Jun 29
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$244 Roundtrip, found 4 days ago
$244
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Fri, Jun 27 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sun, Jun 29, priced at $244 found 4 days ago
Avelo Airlines
Fri, Jun 20 - Thu, Jun 26
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$272 Roundtrip, found 6 days ago
$272
Roundtrip
found 6 days ago
Select Avelo Airlines flight, departing Fri, Jun 20 from Tampa Intl. to Tweed - New Haven Regional, returning Thu, Jun 26, priced at $272 found 6 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 June, 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 $92, 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 $92 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! (1,001 reviews)
Comfy, Convenient, and Cool
"Comfy, clean, and cozy room. Convenient location near major highways in central Connecticut. Our grandson staying with his parents in another room really enjoyed the cool pool."

Reviewed on Jun 7, 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! (689 reviews)
"Great"

Reviewed on Jun 9, 2025

Get rates
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! (1,000 reviews)
"near downtown, you can walk to down town and most corporate locations"

Reviewed on Jun 12, 2025

Get rates
The Capitol Hotel
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! (1,598 reviews)
"Overall, the hotel was amazing to stay at but my one gripe was that the TV remote was very sticky/dirty to touch which was something I never really experienced before and was a bit concerned. But other than that I had a great time and my overall experience was exceptional"

Reviewed on Jun 15, 2025

Get rates
New Haven Hotel
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
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! (1,002 reviews)
"Facility was clean and well kept. Very busy over the holiday weekend. Complementary breakfast was a nice buffet style affair with good selections."

Reviewed on Jun 11, 2025

Get rates
Clarion Inn
La Quinta Inn & Suites by Wyndham New Haven
La Quinta Inn & Suites by Wyndham New Haven
3 out of 5
400 Sargent Dr, New Haven, CT
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
5.8/10 (1,008 reviews)
"Staff were excellent. Neighbors were a bit noisy. Breakfast was good. Elevators were being repaired so staff had to accompany us to manually use the elevator. A little inconvenient but not horrible. Good price for a clean room."

Reviewed on Jun 11, 2025

Get rates
La Quinta Inn & Suites by Wyndham New Haven
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 (1,000 reviews)
"N/A"

Reviewed on May 31, 2025

Get rates
Motel 6 New Haven - Branford, CT
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 ...
7.6/10 Good! (1,139 reviews)
"The surrounding area was not the best, but the hotel was nice for the one night stay."

Reviewed on Jun 11, 2025

Get rates
Best Western Executive Hotel Of New Haven - West Haven
See all 1,137 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.