A stone tower with a metal gate, surrounded by trees and a stone wall.

Cheap Flights to Cheshire , CT from CA $341

View CA $341 flight on Wed, Dec 9, 2026Opens in a new window

Popular airlines to Cheshire

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How much is the cheapest flight to Cheshire?

Prices were available within the past 7 days and start at CA $341 for one-way flights and CA $597 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Sep 19 - Wed, Sep 23
YYZ
Toronto
BDL
Hartford
CA $597 Roundtrip, found 2 days ago
CA $597
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 19 from Toronto to Hartford, returning Wed, Sep 23, priced at CA $597 found 2 days ago
Delta
Tue, Oct 6 - Sat, Oct 17
YYZ
Toronto
BDL
Hartford
CA $599 Roundtrip, found 20 hours ago
CA $599
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Oct 6 from Toronto to Hartford, returning Sat, Oct 17, priced at CA $599 found 20 hours ago
United
Wed, Aug 12 - Wed, Aug 19
YYZ
Toronto
BDL
Hartford
CA $668 Roundtrip, found 14 hours ago
CA $668
Roundtrip
found 14 hours ago
Select United flight, departing Wed, Aug 12 from Toronto to Hartford, returning Wed, Aug 19, priced at CA $668 found 14 hours ago
Air Canada
Sat, Sep 5 - Tue, Sep 8
YYZ
Toronto
BDL
Hartford
CA $732 Roundtrip, found 3 days ago
CA $732
Roundtrip
found 3 days ago
Select Air Canada flight, departing Sat, Sep 5 from Toronto to Hartford, returning Tue, Sep 8, priced at CA $732 found 3 days ago
JetBlue Airways
Thu, Aug 13 - Fri, Aug 28
YVR
Vancouver
BDL
Hartford
CA $871 Roundtrip, found 17 hours ago
CA $871
Roundtrip
found 17 hours ago
Select JetBlue Airways flight, departing Thu, Aug 13 from Vancouver to Hartford, returning Fri, Aug 28, priced at CA $871 found 17 hours ago

Frequently asked questions

What is the name of Cheshire's airport?
Cheshire is served by a single airport, Bradley Intl. Airport (BDL).
What airport is best to fly into Cheshire?
With one major airport operating in Cheshire, it won't take you too long to discover the best flight. You'll be jetting off to Bradley International Airport, which is located around 48 kilometres from downtown.
How many airlines fly to Cheshire?
There are 13 air carriers that fly into Cheshire from 38 airports across the globe.
Which airlines fly to Cheshire?
Flights into Cheshire are typically run by American Airlines. The largest proportion of these flights take off from Washington, with American Airlines servicing this route the most often.
How many nonstop flights are there to Cheshire?
With 489 direct flights operating every week, you'll be landing in Cheshire before you have time to say, "Are we there yet?"
Where are the most popular flights to Cheshire departing from?
A large number of flights to Cheshire set off from Washington, Chicago and Atlanta airports.
How long is the flight to Cheshire Airport?
If you're going to Cheshire from Washington, you're looking at a flight time of 1 hour and 25 minutes. Those setting off from Chicago can expect to be airborne for 2 hours and 7 minutes. From Atlanta it's roughly 2 hours and 11 minutes away.
How to book the cheapest flight to Cheshire?
We all know those lucky jet-setters who somehow land super cheap airfares wherever they go. Would you like to know how to do it for your Cheshire vacation? Don't wait until the very last minute to lock in your flight. Another terrific way to nab an unbeatable deal is to research all options. If where you're headed has more than one airport, be sure to look into the cost of flying into a less busy terminal. And finally, don't forget that it's first in, best dressed. Familiarize yourself with airfare costs and be ready to reserve your seat as soon as you see an unbeatable bargain. The best deals never last long.
Do you have any tips for my flight to Cheshire?
Wherever you're coming from, flying can be a seamless experience if you've prepared well enough. We've put together a list of handy tips and tricks that will get your Cheshire escape started on the right foot. What to pack in your hand luggage:

  • The trick to having a pain-free flight experience is to plan ahead. First up, the essentials: passport, official ID, bank cards and any vital medications. Next, take on board items that'll help keep you occupied, like your laptop or a good book. It's also wise to bring your chargers, a neck pillow and a pair of headphones. Finally, be sure to squeeze in toiletry items like a toothbrush, cleansing wipes and a spare change of clothes.

Do not pack the following items in your hand luggage:

  • Make sure you don't have a Swiss Army knife hiding in the bottom of your carry-on luggage. Other prohibited items include flammable or explosive substances, such as aerosol cans and fuel, and gels and liquids in containers larger than 3.4 ounces (100 millilitres).

What to wear on a flight:

  • You'll want to choose comfort over style. Prepare for changes in temperature by donning layers, and pick flat, closed-toe shoes like sneakers.
  • The result of sustained periods of inactivity, deep vein thrombosis (DVT) is a blood clot condition that can affect some passengers during long flights. Lower your risks by drinking water, keeping your lower limbs moving and wearing compression socks or tights.

How to get through airport security fast when flying to Cheshire?
It's easy — be prepared. We've compiled some helpful hints for a fuss-free trip through security. Look out Cheshire, here you come:

  • Be sure to keep your ID and travel documents easily accessible. They'll be the first things you'll be asked to present to security.
  • After that, both you and your hand luggage will be X-rayed. To make the process quick and painless, remove anything that is likely to set the alarm off. Personal belongings such as your jacket, belt and headphones need to go through the machine.
  • For just a few minutes, you'll need to unplug from the digital world. Your laptop, phone and any other electronic gadgets will need to be sent through the scanner.
  • Any liquids or gels, such as shampoo or hand cream, that you want to bring on board need to be in containers no greater than 3.4 ounces (100 millilitres). Also, they all must fit inside a quart-size (one litre), zip-lock bag.
  • Choosing your footwear wisely can save you a few precious minutes. Hiking or heavy-style boots are often required to be removed and X-rayed separately. Slip-on shoes are usually not.
  • Avoid taking prohibited items in your carry-on bag. If you have any sharp or pointed objects, pack them in your checked baggage. They won't be allowed in the cabin.

Book with confidence

Expedia.ca gives you the best tools to secure great deals on flights to Cheshire. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Cheshire. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Cheshire.

Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Cheshire flights with full confidence knowing that you've found the best deal online.

Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Cheshire.

Looking to save even more? Get additional savings by bundling your Cheshire flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Cheshire trip!

Travel information

Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Destination city name
New Haven
Roundtrip price
CA $133

Trending flights to Cheshire

Prices were available within the past 7 days and start at CA $341 for one-way flights and CA $597 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Sep 19 - Wed, Sep 23
YYZ
Toronto
BDL
Hartford
CA $597 Roundtrip, found 2 days ago
CA $597
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 19 from Toronto to Hartford, returning Wed, Sep 23, priced at CA $597 found 2 days ago

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