Castle Craig at Hubbard Park, Meriden, CT. easily replaceable sky. with a clean, classic view of the tower. Very recognizable image of this historic structure.

$51 Cheap Flights to Cheshire, CT

Popular airlines to Cheshire

How much is the cheapest flight to Cheshire?

Prices were available within the past 7 days and start at $51 for one-way flights and $102 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Frontier Airlines
Avelo Airlines
American Airlines
Southwest Airlines

Alternative airports near Cheshire

Prices were available within the past 7 days. Prices and availability are subject to change.

What you need to know for your flight to Cheshire

Flights to Cheshire at a glance

Traveling to Cheshire is easy; you can choose between full-service and low-cost airlines. By comparing journey times and prices, you can find the cheapest flight to Cheshire that aligns with your budget and plans to explore the city's renowned attractions and neighborhoods.

  • Major airports near Cheshire: Bradley International Airport (BDL), Tweed - New Haven Regional Airport (HVN)
  • Closest (typical) airport to Cheshire: Tweed - New Haven Regional Airport, HVN (around 17 miles)
  • Flights per week: 2,800+ flights arriving across Cheshire airports
  • Number of airlines that fly to Cheshire: around 20+ carriers

Popular airports near Cheshire

Cheshire is a vibrant city ideal for family getaways, outdoor adventures, and cultural experiences. Visitors are drawn to its scenic beauty and lively atmosphere. The city is conveniently accessible, served by two major airports, making travel planning easier for those searching for local airports near Cheshire.

  • Bradley International Airport (BDL): Situated in Hartford County, Connecticut, approximately 31 miles from Cheshire, this airport caters to both domestic and international flights, linking travelers to over 185 U.S. cities and more than 60 international locations. Major airlines like American Airlines, JetBlue Airways, and Delta operate here, with options for first class and premium economy seating available for enhanced comfort on various routes.
  • Tweed - New Haven Regional Airport (HVN): Found in New Haven County, Connecticut, about 17 miles from Cheshire, this airport handles domestic and international flights, connecting approximately 25 domestic cities and 1 international destination. Breeze and Avelo Airlines are among the popular carriers that serve this airport, providing essential travel options for the region.

Top routes to Cheshire

  • Orlando (MCO) to Cheshire (BDL/HVN), with one-way tickets available from around $40
  • Tampa (TPA) to Cheshire (BDL/HVN), with one-way airfare from around $50
  • San Juan (SJU) to Cheshire (BDL/HVN), with one-way flight options from around $80
  • Fort Lauderdale (FLL) to Cheshire (BDL/HVN), with one-way fares starting at around $55
  • Fort Myers (RSW) to Cheshire (BDL/HVN), with one-way flights starting at around $50

Cheapest routes to Cheshire

  • Baltimore (BWI) to Cheshire (BDL/HVN), with low one-way fares from around $30
  • Norfolk (ORF) to Cheshire (BDL/HVN), with low one-way fares from around $30
  • Charleston (CHS/CRW) to Cheshire (BDL/HVN), with low-cost one-way tickets from around $30
  • Richmond (RIC) to Cheshire (BDL/HVN), with low one-way fares from around $35
  • Raleigh (RDU) to Cheshire (BDL/HVN), with affordable one-way prices from around $35

*Flight times and fares vary by season and availability and are based on one-way routes

Top airlines with flights to Cheshire

  • American Airlines: Services Bradley International Airport (BDL) and represents about 33% of arrivals in Cheshire. The typical one-way fare hovers around $280, with first-class service available on select routes.
  • Delta: Operating flights to Bradley International Airport (BDL), Delta accounts for roughly 20% of arrivals to Cheshire. Average one-way fares are around $290, with options for premium economy and first-class service available on certain routes.
  • Southwest Airlines: Serving Bradley International Airport (BDL), Southwest Airlines provides around 15% of arrivals to Cheshire. Travelers can expect an average one-way fare of about $250.
  • JetBlue Airways: With flights to Bradley International Airport (BDL), JetBlue accounts for nearly 8% of arrivals in Cheshire. The average one-way fare is approximately $270, offering premium economy service on select routes.
  • Breeze: Connecting to both Bradley International Airport (BDL) and Tweed - New Haven Regional Airport (HVN), Breeze represents around 7% of arrivals to Cheshire. The average cost for a one-way ticket is about $100.

Best time to fly to Cheshire

The most popular months for travelers to fly to Cheshire are February, March, and April, when peak temperatures in Cheshire can reach up to 48.7°F in April. If you prefer quieter travel, consider September, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 65.8°F. For better deals, May usually offers the lowest average one-way fare around $203, roughly 7% cheaper than the yearly average. Looking for additional cheaper months to fly? September, July, and August offer average one-way fares of around $208, making them good options for flexible travelers.

calendar iconMonthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinesscrowd level iconDemandprice iconAverage one-way Fare
January29.1°F (-1.6°C)Light RainMostly SunnyAverage$227
February30.7°F (-0.7°C)Light RainMostly CloudyHigh$223
March37.9°F (3.3°C)Light RainMostly SunnyHigh$231
April48.7°F (9.3°C)Light RainMostly SunnyHigh$250
May59.2°F (15.1°C)Light RainMostly SunnyAverage$203
June67.5°F (19.7°C)Light RainMostly SunnyAverage$211
July74.3°F (23.5°C)Light RainMostly SunnyAverage$209
August72.7°F (22.6°C)Light RainMostly SunnyAverage$210
September65.8°F (18.8°C)Light RainMostly SunnyLow$207
October55.0°F (12.8°C)Light RainMostly SunnyAverage$215
November43.3°F (6.3°C)Light RainMostly SunnyLow$225
December35.4°F (1.9°C)Light RainMostly SunnyLow$225

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

How to save money on a flight to Cheshire

Getting some of the best deals on flights to Cheshire is all about timing and flexibility. Here are some key tips to help you save:

  1. Compare flight options—use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  2. Set up price alerts—as an Expedia member you can use Price Tracking to receive notifications when flight prices change.
  3. Bundle and save—book a flight and unlock a hotel deal on Expedia*, or explore our Cheshire hotel and flight deals.
  4. Think about luggage-nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your baggage allowance before confirming your booking to avoid excess baggage fees at the airport.
  5. Earn miles—you can earn airline miles when you book your Cheshire flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Cheshire

Cheshire welcomes travelers through its range of transport options based on price, convenience, and proximity. Here's how to reach Cheshire efficiently:

  • Public transportation: From Bradley International Airport, Windsor Locks Station, a train station, is located about 5 miles away by car, providing convenient access for travelers needing rail connections.
  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Cheshire, with private rides that can be arranged in advance.
  • Car rental: Renting a car in Cheshire is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Cheshire on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.

Where to stay around Cheshire

  • Waterbury: Waterbury is located 8 miles drive away from Cheshire. This vibrant city offers a blend of family-friendly activities and outdoor adventures. Visitors can explore the thrilling rides at Lake Compounce amusement park, delve into culture at Quinnipiac University, or appreciate local art at the Mattatuck Museum Arts and History Center. Waterbury’s attractions cater to a variety of interests, making it a great day trip for families or anyone seeking an urban experience with plenty of options for fun and education.
  • Hamden: Hamden is located 9 miles drive away from Cheshire. Known for its cultural richness and outdoor spaces, Hamden invites travelers to experience the historic Yale University and the scenic beauty of Sleeping Giant State Park. Families can enjoy a day out at the local beaches or engage in activities at nearby golf courses. This city truly embodies the charm of Connecticut, making it a wonderful spot for those looking to immerse themselves in both nature and history.
  • Meriden: Meriden is located 6 miles drive away from Cheshire. This city blends family fun and cultural experiences, highlighted by attractions such as Wesleyan University and the exciting Lake Compounce amusement park. Visitors can also explore Choate Rosemary Hall, a modern college that adds to the area's educational appeal. Meriden provides a perfect balance of outdoor activities and cultural sites, making it an ideal stop for anyone traveling in the region.

Tips for short-haul flights to Cheshire

For quick getaways, efficiency is key. Here is how to make your short-haul journey smoother:

  • Pack light and skip checked bags—when flying with budget airlines, it's often more economical to travel with just a carry-on. Maximize your space by opting for mini toiletries, wearing your bulkiest clothing, and planning your outfits wisely. This approach also helps you avoid the wait at baggage claim upon arrival.
  • Bring your own entertainment—many short-haul flights may lack in-flight entertainment. To stay entertained, download your favorite TV shows, movies, music, or podcasts ahead of time, and consider bringing a book. Remember to fully charge your devices before you board.
  • Arrive at the airport in plenty of time—even for short or domestic flights, it's advisable to arrive at least 1.5 to 2 hours prior to departure, allowing for traffic and security lines.
  • Bring your own snacks and water—pack some snacks and a refillable water bottle to stay hydrated and save money at the airport.

Tips for long-haul flights to Cheshire

Flying long-haul sometimes requires extra planning to ensure a comfortable journey:

  • Select your seat in advance—for longer flights, choosing your seat is essential for comfort. Full-service airlines often allow free seat selection once online check-in opens, typically 24–48 hours before your flight. Some airlines may even permit seat selection earlier.
  • Arrive at the airport in plenty of time—make sure to arrive at least 3 hours before departure for international flights to account for check-in, security, and immigration procedures.
  • Relax at the airport—if you have some extra time, take the opportunity to explore the shops, enjoy a coffee at a café, or unwind at the gate or in a departure lounge if you have access. Most airports provide free and accessible Wi-Fi.
  • Adjust to the new time zone mid-flight—begin syncing your body clock by setting your watch and modifying your sleep schedule to align with your destination's time zone. Try to either sleep or stay awake on the flight according to the local time at your arrival destination to help minimize jet lag.

Frequently asked questions

What month is the cheapest to fly to Cheshire?
Schedule your trip for September if you're hoping to get a deal on your fare. It's the cheapest month to fly to Cheshire. Try to avoid traveling during busy periods such as public holidays or major events.
Which US cities have the cheapest flights to Cheshire?
Score cheap flights to Cheshire from Washington, Chicago and Orlando. These cities usually offer the best fares to this much-loved destination. But bear in mind that stopovers, holiday periods and demand will also have an impact on rates, so remain flexible and book when prices are right.
Which US cities fly direct to Cheshire?
Choose from 32 US destinations with direct flights to Cheshire. When booking on Expedia, check the "Direct flights only" box to compare nonstop options. Fly to Cheshire from any of these leading cities:

  • Washington
  • Chicago
  • Orlando
  • Atlanta
  • Charlotte

How to find a cheap flight to Cheshire?
To secure cheap flights to Cheshire, book in advance and visit during the off-season months of December and January. Want a handy tip? Take off on a Thursday and save 16% on average compared to traveling on a Sunday.* Set a price alert on the Expedia app and you'll get notified as soon as your fares go down.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Cheshire?
Staying flexible with your plans might help you to find last-minute offers on cheap flights to Cheshire. To view all the available options, try exploring different ticket types, tweaking your Cheshire vacation dates, leaving from an alternative airport or going with another carrier.
How far in advance should I book a flight to Cheshire?
Get the travel dates you want and a price you'll love by booking your domestic flight to Cheshire up to 28 days in advance. Lock in tickets between two and four months ahead if you're headed to Cheshire from an international destination.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Cheshire?
Sundays are typically the best day to book a cheap flight to Cheshire, with savings of around 8% on average compared to a Friday. If you purchase tickets on a Friday, expect to spend more as this is typically the most expensive day.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Cheshire?
A total of 10 carriers connect 34 airports all over the world to Cheshire. Here are some of the major airlines to Cheshire, where Bradley Intl. Airport (BDL) is the major entry point:

  • Delta Air Lines
  • American Airlines
  • United Airlines
  • JetBlue Airways

Where do you fly into Cheshire?
When flying to Cheshire, the main airport to land at is Tweed - New Haven Regional Airport (HVN). You can also head to nearby hubs like Hartford, CT (HFD-Hartford - Brainard), Bradley Intl. Airport (BDL) or MacArthur Airport (ISP). Another possibility worth keeping in mind when you fly to Cheshire is Westchester County Airport (HPN).
How far is the airport from central Cheshire?
You'll be roughly 17 mi south of central Cheshire after landing at Tweed - New Haven Regional Airport (HVN).
Can I save money by booking a Cheshire trip package?
You could possibly save hundreds of dollars if you choose a Cheshire flight and hotel package deal on Expedia. And you'll save yourself hassle by having all your travel plans in one place. Try bundling flights and accommodations with add-ons like activities and car rentals for your own customized Cheshire escape.
Can I change or cancel my flight to Cheshire?
You can usually change or cancel your flight to Cheshire within 24 hours of booking. However, be mindful that some flights are non-refundable. In those cases, you may receive a credit toward a future flight rather than a direct refund. Be sure to check the airline's terms of service in your itinerary for exact details. Use Expedia's "Changes included" or "No cancel fee" filters during your search to secure cheap flights to Cheshire with flexible change policies. For more information, head to our Customer Service Portal.

*Flight schedules are subject to change.

*Available to One Key members.

 

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Travel information

Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Destination city name
New Haven
Roundtrip price
$101

Trending flights to Cheshire

Prices were available within the past 7 days and start at $51 for one-way flights and $102 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways

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