Cheap flights To Cheshire (BDL) from $51

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Cheap Flights to Cheshire from $51 One Way, $111 Round Trip

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

Thu, Jan 21 - Sun, Jan 31
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$111 Roundtrip, found 13 hours ago
$111
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Thu, Jan 21 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jan 31, priced at $111 found 13 hours ago
Thu, Jan 21 - Sun, Jan 31
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$116 Roundtrip, found 13 hours ago
$116
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Thu, Jan 21 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jan 31, priced at $116 found 13 hours ago
Thu, Jan 21 - Sun, Jan 31
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$121 Roundtrip, found 13 hours ago
$121
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Thu, Jan 21 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jan 31, priced at $121 found 13 hours ago
Thu, Jan 21 - Sun, Jan 24
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$125 Roundtrip, found 5 days ago
$125
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jan 21 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jan 24, priced at $125 found 5 days ago
Thu, Jan 28 - Sun, Jan 31
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$127 Roundtrip, found 6 days ago
$127
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Jan 28 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jan 31, priced at $127 found 6 days ago
Fri, Jan 8 - Sun, Jan 10
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$136 Roundtrip, found 6 hours ago
$136
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Fri, Jan 8 from Tampa Intl. to Tweed - New Haven Regional, returning Sun, Jan 10, priced at $136 found 6 hours ago
Fri, Dec 11 - Mon, Dec 14
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$140 Roundtrip, found 4 days ago
$140
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Dec 11 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Dec 14, priced at $140 found 4 days ago
Fri, Jan 8 - Sun, Jan 10
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$141 Roundtrip, found 6 hours ago
$141
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Fri, Jan 8 from Tampa Intl. to Tweed - New Haven Regional, returning Sun, Jan 10, priced at $141 found 6 hours ago
Fri, Nov 13 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$142 Roundtrip, found 2 days ago
$142
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Nov 13 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Nov 16, priced at $142 found 2 days ago
Thu, Nov 5 - Mon, Nov 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$152 Roundtrip, found 6 hours ago
$152
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Thu, Nov 5 from Orlando Intl. to Bradley Intl., returning Mon, Nov 9, priced at $152 found 6 hours ago

Cheshire Flight Information

Traveling To
Cheshire
Destination Airport IATA Code
BDL
Number of Airlines Serving
Airlines
Breeze Airways
Flight Price
$111
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Cheshire economy flight packages

Price found within the past 48 hours. Click for updated prices.
Whitney Inn & Suites
2.0-star property

Whitney Inn & Suites

Nov 7 - Nov 14

7 night stay

Tampa (TPA) to New Haven (HVN)

Breeze Airways • Roundtrip • Coach
Price was $613, price is now $544 per person
$544
per person
found 17 hours ago
Clarion Inn North Haven - New Haven North
3.0-star property

Clarion Inn North Haven - New Haven North

Nov 7 - Nov 14

7 night stay

Tampa (TPA) to New Haven (HVN)

Breeze Airways • Roundtrip • Coach
Price was $725, price is now $600 per person
$600
per person
found 17 hours ago
Cheshire Welcome Inn
2.5-star property

Cheshire Welcome Inn

Nov 7 - Nov 14

7 night stay

Tampa (TPA) to New Haven (HVN)

Breeze Airways • Roundtrip • Coach
Price was $614, price is now $560 per person
$560
per person
found 17 hours ago
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Cheshire

Orbitz uses cutting edge mobile technology to help get you the best deals on Cheshire flights. We offer guaranteed low prices on air tickets that can be combined with hotels and car rentals to save you even more money.

Find Cheap Cheshire Flights And Hotel Rooms Using Our Mobile App

Orbitz not only guarantees low prices for flights to Cheshire, we also offer Mobile Steals on our Orbitz on the Go mobile app where you can find great mobile-only deals on hotel rooms in the area.

Use the Orbitz Flight Matrix To Save Big On Car Rental

Discount flights to Cheshire can be combined with car rental to get you additional savings. Just use our Flight Matrix to see how your budget air ticket can be combined with a car rental to make your trip not only inexpensive but also more convenient.

Use Multiple Airlines To Ensure You Get The Best Deal

Orbitz allows you to use multiple airlines for flights to Cheshire. By using a combination of airlines for discount flights you are guaranteed to get the lowest fares each way and get the schedule that is most convenient for you.

Store Your Frequent Flyer Information on Orbitz For Easy Access

Booking with Orbitz will still allow you to apply miles for flights to Cheshire to your frequent flyer program. Not only that, but your frequent flyer information will be safely stored on our website, so it will be easy to access the next time you book a discount air ticket with Orbitz.

Frequently asked questions

Which airlines fly to Cheshire?
Purchase a fare with one of the 20 airlines that travel to Bradley Intl. Airport (BDL) and this awesome city will be yours to explore. Whenever you want to escape, you'll find a flight that suits your budget. Have a look at these popular international carriers that touch down in Cheshire:

  • Air Canada - 17 flights to Cheshire per month
  • JetBlue - 16 flights to Cheshire per month

What is the best airport to fly to in Cheshire?
Keep an eye out for an amazing airfare to Bradley Intl. Airport (BDL). It's the city's main terminal and is situated roughly 30 miles north of the downtown area. Once you've strolled out of arrivals, it won't be long before you're experiencing the best of Cheshire.
How much is a flight to Cheshire?
Travelers from far and wide picked up return-flight bargains ranging between $111 and $152 this week to Cheshire. Starting your trip from Orlando (MCO)? The best one-way tickets were just $51.
How to book the cheapest flight to Cheshire?
Landing cheap flights to Cheshire is as simple as booking with Orbitz. But if you're eager to make sure you're getting the best flight deals around, here are some suggestions your wallet will love:

  • Consider departing from or arriving at nearby airports to increase your savings. Enter your preferred departure and arrival airports in the form fields, then click on the 'Nearby airports' function below. It will show you any available options.
  • If your plans aren't set in stone, click on the 'Show flexible dates' option to scan the flight deals for different departure dates. You may find an amazing fare.
  • To optimize your results, click on 'Show options.' You can search based on seating class, airlines, and nonstop and refundable flights. You can also choose whether you want to fly in the morning, afternoon or evening under 'Sort & Filter' to the left.
  • The early bird catches the best savings, so book as soon as you know your travel dates. The most affordable fares go like hotcakes and prices normally climb as the departure date gets closer.
  • Consider bundling your flights, hotels and car rentals into one convenient package deal — the more you book, the more you save.
  • If it's an option, avoid traveling in peak seasons. Airfares soar during summer, school breaks and other vacation periods like Easter and Thanksgiving.

How long is a flight to Cheshire?
Naturally, flight times differ depending on where you're leaving from. But to give you a clearer idea of the average duration, take a peek at these busy routes to Cheshire:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 10 minutes
  • Orlando, FL (MCO-Orlando Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 39 minutes
  • Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) to Bradley Intl. Airport (BDL) - 1 hour and 25 minutes

What is the best time to book a flight to Cheshire?
If possible, book your flights to Cheshire in January. This is the best month to reserve low airfares, followed by February and August. With a little planning, you're sure to find a cheap flight with Orbitz.
What day of the week is the cheapest to book a flight to Cheshire?
Typically, Tuesdays, Wednesdays and Saturdays are the cheapest days to book a flight to Cheshire. If you want the best airfares, search across those days and you just might score yourself a fantastic flight deal.
What is the cheapest day of the week to fly to Cheshire?
If you're looking for cheap flights to Cheshire, depart early in the week. Orbitz data from 2020 shows Monday is the most affordable day to set off, followed by Tuesday. Saturday is the most expensive, so avoid this day and do your budget a favor.
What is the cheapest month to fly to Cheshire?
Jet off sometime in August if you don't want to eat into your budget. Orbitz data shows that this is generally the best month for cheap flights to Cheshire. June is when prices are at their highest.
Which airlines allow free cancellation?
We know that plans can change and flexibility is more important than ever. That's why you can search for flights that have free cancellation and no change fees on Orbitz. Simply click on "Filter by flexible change policies" and we'll show you fares with more flexibility than candy on a dashboard in summer!
What do I need for the flight to Cheshire?
The trick to a comfortable and stress-free flight is being well prepared. Listed below are a few tips to help you get ready for departure:

  • Whether you print it out at home or use an electronic one, you'll need your boarding pass to get on to the plane. You'll also need some form of government-issued photo identification. If you're flying internationally, make sure your passport is valid and you've checked visa requirements.
  • Take some activities to keep you busy on your journey to Cheshire. Magazines and electronic gadgets like tablets and e-readers are ideal. Be sure to take a refillable water bottle with you too. Even on a short flight, it's important to stay well-hydrated.
  • Even if you're flying when it's 100 degrees outside, carry a cardigan or sweater on board with you. Cabins can get downright chilly.

How many direct flights are there to Cheshire?
You can book a seat on one of 175 flights that travel directly to Cheshire each month. American Airlines, Delta Air Lines and Southwest Airlines are just a couple of the carriers that will take you there comfortably in one go. United Airlines, JetBlue Airways and Spirit Airlines also fly to Cheshire nonstop.
How do I get cheap first-class/business deals to Cheshire?
If you think a first or business-class fare is out of your reach, you may want to think again. Here are a few practical tips to help you land a premium flight to Cheshire for less:

  • Be flexible with your travel dates and hold out for exclusive offers or sales on first or business-class airfares.
  • Low-cost airlines offer first or business-class seats at a fraction of the usual cost. Ditch the full-service carriers and fly with one these cheaper options.
  • Make the most of your airline's flight rewards program and upgrade your seat. Alternatively, you can try bidding for an upgrade in an online auction.

How to get into Cheshire from the airport?
A Bradley Intl. Airport (BDL) car rental is a quick way of getting from BDL airport to downtown Cheshire. Pick up a vehicle from one of the major rental outlets on-site, like Payless, Budget or Alamo and then head south. You'll need to drive about 30 miles to reach the city center. Cheshire car rentals is another popular option located downtown if you'd prefer not to drive so soon after your plane lands.
What is the best time to go to Cheshire?
Cheshire is a busy place in May, June and August. If you're planning to visit during these months, it may be an idea to book early to ensure you get the best deals. Wondering what summertime's like in Cheshire? Average daily temperatures typically sit between 65 ºF and 80 ºF. Like most of the Northern Hemisphere, the summer season starts June 20 here.
Travel tips for Cheshire

  • Kick off your sightseeing in the downtown area and take a walking tour of a few of the city's awesome attractions. Cheshire Golf Course and Cheshire Hollow Farm are a couple of visitor favorites.
  • If you're looking for a day trip, there are more sights that'll impress you a short drive out of town. Discover why Yale University and Trinity College are on the itineraries of most Cheshire visitors.
  • When you're ready to discover more of Connecticut, lock in a car rental and travel in the direction of Stamford. Norwalk is another worthwhile city with no shortage of things to see and do.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.