Cheap flights To Cheshire (BDL) from $34

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Cheap Flights to Cheshire from $34 One Way, $63 Round Trip

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

Sat, Jan 10 - Sat, Jan 10
MCO
Orlando Intl.
BDL
Bradley Intl.
$63 Roundtrip, found 6 days ago
$63
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Jan 10 from Orlando Intl. to Bradley Intl., returning Sat, Jan 10, priced at $63 found 6 days ago
Fri, Dec 12 - Fri, Dec 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$64 Roundtrip, found 13 hours ago
$64
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Fri, Dec 12 from Orlando Intl. to Bradley Intl., returning Fri, Dec 12, priced at $64 found 13 hours ago
Fri, Jan 16 - Mon, Jan 19
MCO
Orlando Intl.
BDL
Bradley Intl.
$68 Roundtrip, found 10 hours ago
$68
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Fri, Jan 16 from Orlando Intl. to Bradley Intl., returning Mon, Jan 19, priced at $68 found 10 hours ago
Thu, Dec 25 - Sat, Jan 10
MCO
Orlando Intl.
BDL
Bradley Intl.
$69 Roundtrip, found 9 hours ago
$69
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Thu, Dec 25 from Orlando Intl. to Bradley Intl., returning Sat, Jan 10, priced at $69 found 9 hours ago
Sun, Dec 28 - Thu, Jan 1
MCO
Orlando Intl.
BDL
Bradley Intl.
$70 Roundtrip, found 8 hours ago
$70
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sun, Dec 28 from Orlando Intl. to Bradley Intl., returning Thu, Jan 1, priced at $70 found 8 hours ago
Fri, Dec 12 - Mon, Dec 15
MCO
Orlando Intl.
BDL
Bradley Intl.
$77 Roundtrip, found 13 hours ago
$77
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Fri, Dec 12 from Orlando Intl. to Bradley Intl., returning Mon, Dec 15, priced at $77 found 13 hours ago
Fri, Dec 5 - Mon, Dec 8
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$78 Roundtrip, found 8 hours ago
$78
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Fri, Dec 5 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Dec 8, priced at $78 found 8 hours ago
Thu, Dec 25 - Sat, Jan 10
MCO
Orlando Intl.
BDL
Bradley Intl.
$81 Roundtrip, found 9 hours ago
$81
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Dec 25 from Orlando Intl. to Bradley Intl., returning Sat, Jan 10, priced at $81 found 9 hours ago
Thu, Dec 11 - Sun, Dec 14
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$82 Roundtrip, found 10 hours ago
$82
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Thu, Dec 11 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 14, priced at $82 found 10 hours ago
Fri, Dec 5 - Mon, Dec 8
MCO
Orlando Intl.
BDL
Bradley Intl.
$88 Roundtrip, found 6 hours ago
$88
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Fri, Dec 5 from Orlando Intl. to Bradley Intl., returning Mon, Dec 8, priced at $88 found 6 hours ago

Cheshire Flight Information

Traveling To
Cheshire
Destination Airport IATA Code
BDL
Number of Airlines Serving
Airlines
Frontier Airlines, Breeze Airways
Flight Price
$63
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.
Residence Inn by Marriott Hartford/Windsor
3.0-star property

Residence Inn by Marriott Hartford/Windsor

Dec 27 - Dec 30

3 night stay

Fort Myers (RSW) to New Haven (HVN)

American Airlines • Non-stop • Coach

New Haven (HVN) to Fort Myers (RSW)

Southwest Airlines • Non-stop • Coach
Price was $559, price is now $547 per person
$547
per person
found 19 hours ago
Hilton Garden Inn Hartford North/Bradley Int'l Airport
3.0-star property

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Dec 27 - Dec 30

3 night stay

Fort Myers (RSW) to New Haven (HVN)

American Airlines • Non-stop • Coach

New Haven (HVN) to Fort Myers (RSW)

Southwest Airlines • Non-stop • Coach
Price was $616, price is now $569 per person
$569
per person
found 19 hours ago
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Cheshire first class flight packages

Price found within the past 48 hours. Click for updated prices.
Quality Suites
2.5-star property

Quality Suites

8/10 Very Good! (1,024 reviews)

Dec 26 - Dec 30

4 night stay

Knoxville (TYS) to New Haven (HVN)

American Airlines • Non-stop roundtrip • FirstClass
Price was $785, price is now $785 per person
$785
per person
found 1 day ago
Nice person at front desk.

Reviewed on Jun 15, 2025

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Cheshire

Are you in the mood for a cruise? Shop Orbitz today for cheap cruises and flights to Cheshire. Our award-winning cruise site features exclusive offers, information for first-timers and top destinations and activities. Make discount domestic and international travel plans in an instant with cutting-edge mobile tools from Orbitz.

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First-Timers

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Ports and Play

Be sure to check our cruise page for free shore excursions, onboard spending, balcony upgrades and other perks. Orbitz offers last-minute, luxury, weekend and summer cruises. You can even designate which port you want to sail from and pre-book on-shore activities. Get there on the cheap with discounts on flights to Cheshire and Cheshire flights. Get more bang for your travel buck at 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 $63 and $88 this week to Cheshire. Starting your trip from Orlando (MCO)? The best one-way tickets were just $34.
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.