$34 Cheap Flights to Chesterfield, MA

Flights to Chesterfield at a glance

Traveling to Chesterfield is easy—simply select from a range of full-service or budget airlines, compare travel durations, and choose the option that fits your budget and itinerary as you plan to explore the city's renowned attractions and neighborhoods.

• Major airport near Chesterfield: Bradley International Airport (BDL)
• Flights per week: 2,650+ flights arriving at Chesterfield airport
• Number of airlines that fly to Chesterfield: around 20+ carriers

Popular airport near Chesterfield

Chesterfield is a charming city known for its outdoor activities, stunning scenery, and adventurous getaways. Visitors are drawn to its blend of romance, culture, and urban attractions. The city is conveniently accessed via a major airport, making travel easy for explorers.

• Bradley International Airport (BDL): Situated in Hartford County, Connecticut, approximately 33 miles from Chesterfield, this airport facilitates both domestic and international travel. It connects passengers to over 185 domestic cities and more than 60 international destinations. Travelers can enhance their journey by opting for first class or premium economy seating, depending on the airline and route. Notable airlines operating here include American Airlines, JetBlue Airways, and Delta.

Top routes to Chesterfield

• Orlando (MCO) to Chesterfield (BDL), with one-way flight options from around $45
• Tampa (TPA) to Chesterfield (BDL), with one-way flight options from around $60
• San Juan (SJU) to Chesterfield (BDL), with one-way flights starting at around $80
• Fort Lauderdale (FLL) to Chesterfield (BDL), with one-way flights starting at around $75
• Fort Myers (RSW) to Chesterfield (BDL), with one-way tickets available from around $55

Cheapest routes to Chesterfield

• Richmond (RIC) to Chesterfield (BDL), with cheap one-way fares from around $45
• New York (JFK) to Chesterfield (BDL), with low one-way fares from around $45
• Orlando (MCO) to Chesterfield (BDL), with affordable one-way prices from around $45
• Norfolk (ORF) to Chesterfield (BDL), with budget one-way fares from around $45
• Miami (MIA) to Chesterfield (BDL), with cheap one-way fares from around $50

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

Top airlines with flights to Chesterfield

• American Airlines: Operating flights to Bradley International Airport (BDL), this airline represents about 33% of Chesterfield's arrivals. Passengers can expect an average one-way fare of around $280, with options for premium service that may include first class based on the route.
• Delta: Serving Bradley International Airport (BDL), Delta accounts for roughly 20% of arrivals to Chesterfield. The average one-way fare is about $290, and travelers can enjoy premium cabin choices, which may feature both premium economy and first class depending on the flight path.
• Southwest Airlines: With flights to Bradley International Airport (BDL), Southwest Airlines contributes around 15% of arrivals to Chesterfield. The typical one-way fare is approximately $250, offering a good value for travelers.
• JetBlue Airways: JetBlue operates flights to Bradley International Airport (BDL), making up around 8% of Chesterfield's arrivals. The average one-way fare is close to $270, with premium service that may include premium economy depending on the specific route.
• Breeze: This airline flies into Bradley International Airport (BDL), responsible for about 6% of arrivals to Chesterfield. The average one-way fare is quite affordable at approximately $120, making it an attractive option for budget-conscious travelers.

Best time to fly to Chesterfield

The most popular months for travelers to fly to Chesterfield are February, March, and April, when peak temperatures in Chesterfield can reach up to 47.1°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 63.7°F. For better deals, May usually offers the lowest average one-way fare around $206, 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 $210, making them good options for flexible travelers.

*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 Chesterfield

Getting some of the best deals on flights to Chesterfield 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 Chesterfield 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 Chesterfield flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Chesterfield

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

• Public transportation: From Bradley International Airport, Windsor Locks Station, a train station, is conveniently located about 5 miles away by car, providing easy access for travelers looking to continue their journey.
• Hotel transfer: Transfers offer a convenient way to reach your hotel in Chesterfield, with private rides that can be arranged in advance.
• Car rental: Renting a car in Chesterfield is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Chesterfield 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 Chesterfield

• Haydenville: Located 9 miles drive away from Chesterfield, Haydenville is a charming village that offers a blend of cultural experiences and outdoor activities. Visitors can immerse themselves in the local arts scene, with venues for theater and educational pursuits nearby. Notable attractions include the University of Massachusetts Amherst, a modern college perfect for city vacations, and Smith College, renowned for its historic significance. The area is also home to Historic Northampton, a museum that invites travelers to explore the rich history of the region.
• Northampton: Northampton, situated 12 miles drive away from Chesterfield, is a vibrant city celebrated for its cultural richness and outdoor opportunities. This dynamic locale features a variety of music concerts and educational institutions, making it a hub for arts and entertainment. Explore the iconic University of Massachusetts Amherst and the historic Smith College, both of which enhance the city's cultural landscape. Additionally, Historic Northampton offers a glimpse into the past, enriching your visit with historical insights and experiences.
• Easthampton: Easthampton is located 12 miles drive away from Chesterfield and is an ideal destination for outdoor enthusiasts and families seeking adventure. The city is dotted with scenic hiking trails and recreational spots, ensuring plenty of opportunities for exploration. Key highlights include the historic Smith College and the Big E, an entertainment arena that caters to family fun. Nature lovers will enjoy Nashawannuck Pond, a beautiful water feature that adds to the city's charm. Whether you're looking for adventure or a relaxing day outdoors, Easthampton has something for everyone.

Tips for short-haul flights to Chesterfield

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. Save space by using mini toiletries, wearing your bulkiest clothing, and planning your outfits wisely. This also allows you to avoid the wait at baggage claim upon arrival.
• Bring your own entertainment—many short-haul flights may lack in-flight entertainment options. Download your favorite TV shows, movies, music, or podcasts ahead of time, and consider bringing a book to keep yourself entertained. 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 before your departure, taking into account potential traffic and security lines.
• Bring your own snacks and water—pack some snacks and a refillable water bottle to stay hydrated and save money while at the airport.

Tips for long-haul flights to Chesterfield

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 typically allow free seat selection once online check-in opens, which is usually 24–48 hours before your flight. Some airlines may provide seat selection options even earlier.
• Arrive at the airport in plenty of time—make it a point to arrive at least 3 hours before departure for international flights to accommodate check-in, security, and immigration procedures.
• Relax at the airport—if you have some extra time, take the opportunity to explore the shops, find a coffee shop, or unwind at the gate or in a departure lounge if you have access. Airport Wi-Fi is generally free and widely available.
• Adjust to the new time zone mid-flight—begin syncing your body clock by changing your watch and adjusting your sleep schedule to align with your destination's time zone. Try to sleep or stay awake during the flight according to the local time at your arrival destination to help minimize jet lag.

Tips to find the cheapest flights to Chesterfield

The cheapest day to fly

Get started finding a cheap flight to Chesterfield on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

The cheapest month to fly

October is the cheapest month to fly to Chesterfield. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Chesterfield. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute.

The most affordable time to book a flight

Typically, a Sunday can be the cheapest time to book a flight to Chesterfield, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation.

The cheapest round-trip tickets to Chesterfield

The lowest price for round-trip flights to Chesterfield in 2026 starts from $78, while one-way tickets start from from $34. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Chesterfield. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Chesterfield

Frontier Airlines, Breeze Airways, Southwest Airlines, Delta, United, American Airlines are just some of the airlines that can typically offer cheap tickets to Chesterfield. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Chesterfield and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Chesterfield, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Chesterfield. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia.

Save with a package

With Expedia's amazing package deals, you could save hundreds of dollars by booking your Chesterfield plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving.

Date flexibility for the cheapest flights to Chesterfield

If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Chesterfield.

Stopover savings

The cheapest tickets to Chesterfield are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Chesterfield. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved.

Get Expedia's Price Drop Protection

Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference*. This gives you peace of mind that you're getting one of the cheapest flights to Chesterfield for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members.

*Terms apply.

Use our Price Tracking feature

Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Chesterfield. Simply download the free Expedia app to your smart device and activate Chesterfield flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices.

Book with Expedia

As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Chesterfield. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.