$44 Cheap Flights to Chesterfield, VA

Flights to Chesterfield at a glance

Traveling to Chesterfield is easy—explore various flight routes with both full-service and affordable airlines. Compare journey times and select the best option that aligns with your budget and schedule, allowing you to fully enjoy the city's renowned sights and neighborhoods.

• Major airport near Chesterfield: Richmond International Airport (RIC)
• Flights per week: 2,400+ flights arriving at Chesterfield airport
• Number of airlines that fly to Chesterfield: around 25+ carriers

Popular airport near Chesterfield

Chesterfield, a vibrant city in Virginia, is an ideal destination for families and outdoor enthusiasts alike. Visitors are drawn to its scenic beauty and urban charm. Travelers can access Chesterfield via the nearby Richmond International Airport (RIC) and Chesterfield County Airport, which offer various domestic flights.

• Richmond International Airport (RIC): Situated in Henrico County, Virginia, approximately 13 miles from Chesterfield, this airport offers a range of domestic and international flights, linking to over 180 domestic cities and more than 65 international locales. Travelers can opt for enhanced comfort by selecting first-class or premium economy service based on the airline and route. Major carriers operating from Richmond include American Airlines, Delta, and JetBlue Airways.

Top routes to Chesterfield

• Orlando (MCO) to Chesterfield (RIC), with one-way tickets available from around $50
• Boston (BOS) to Chesterfield (RIC), with one-way fares starting at around $75
• New York (JFK/LGA) to Chesterfield (RIC), with one-way airfare from around $90
• Fort Lauderdale (FLL) to Chesterfield (RIC), with one-way fares starting at around $60
• Las Vegas (LAS) to Chesterfield (RIC), with one-way fares starting at around $110

Cheapest routes to Chesterfield

• New Haven (HVN) to Chesterfield (RIC), with low one-way fares from around $35
• Baltimore (BWI) to Chesterfield (RIC), with cheap one-way fares from around $40
• Hartford (BDL) to Chesterfield (RIC), with low-cost one-way tickets from around $40
• Providence (PVD) to Chesterfield (RIC), with low-cost one-way tickets from around $45
• Orlando (MCO) to Chesterfield (RIC), with budget 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: Operates flights to Richmond International Airport (RIC), representing approximately 38% of Chesterfield's arrivals. The average fare for a one-way ticket is around $290, with the possibility of first-class service available based on the route.
• Delta: Provides service to Richmond International Airport (RIC), making up about 26% of the arrivals in Chesterfield. Travelers can expect an average one-way fare of roughly $280, with premium options available, including premium economy and first class, depending on the route.
• United: Flies into Richmond International Airport (RIC), accounting for around 14% of Chesterfield's incoming flights. The typical one-way fare stands at approximately $300, with first-class service as a premium option depending on the specific route.
• Southwest Airlines: Serves Richmond International Airport (RIC), contributing about 10% of arrivals to Chesterfield. Average one-way fares are estimated at around $260, providing a cost-effective option for travelers.
• JetBlue Airways: Flies to Richmond International Airport (RIC), representing roughly 6% of the arrivals in Chesterfield. The average fare for a one-way ticket hovers around $240, with premium economy service available based on route specifics.

Best time to fly to Chesterfield

The most popular months for travelers to fly to Chesterfield are January, March, and April, when peak temperatures in Chesterfield can reach up to 58.6°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 72.1°F. For better deals, May usually offers the lowest average one-way fare around $216, roughly 7% cheaper than the yearly average. Looking for additional cheaper months to fly? August, October, and September offer average one-way fares of around $222, 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 Richmond International Airport, Richmond Seaport, a seaport, is located about 7.9 miles away by car, while Richmond Main Street Station, a train station, is approximately 8.2 miles from the airport and also accessible by car.
• 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 in and around Chesterfield

• Chester: Located 4 miles away from Chesterfield, Chester is a city that offers a blend of family-friendly and business experiences. This vibrant destination features a shopping mall center and an arcade adventure zone, perfect for a day of fun. Don't miss the historic Virginia State University for a dose of culture, or the natural beauty of Pocahontas State Park, ideal for outdoor enthusiasts. For thrill-seekers, the nearby theme park provides a fantastic escape. Explore the Dutch Gap Conservation Area for a serene day in nature.
• Hampton Park: Situated around the area of Chesterfield, Hampton Park is a charming neighborhood well-suited for outdoor activities and family outings. With a variety of shopping centers and educational venues, it’s an excellent spot for a leisurely day. The local attractions include Pocahontas State Park, where adventure and scenic views await, and the University of Richmond, a modern college that enriches the community. Virginia Commonwealth University also offers a glimpse into Chesterfield's rich cultural landscape, making Hampton Park perfect for those seeking a city experience.
• Chesterfield Court House: Chesterfield Court House is located in the area of Chesterfield and is an appealing village for outdoor lovers. With easy access to recreational areas and parks, it invites visitors to enjoy nature and engage in various activities. Key points of interest include the expansive Pocahontas State Park, ideal for adventure seekers, and Castlewood, a historic house that reflects the area’s rich history. For a peaceful retreat, Maymont Park offers a beautifully landscaped private garden, perfect for a relaxing stroll amidst stunning surroundings.

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—with budget airlines, traveling with just a carry-on is often the more economical choice. Maximize your space by bringing mini toiletries, wearing your bulkiest clothing, and planning your outfits strategically. 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 options. Download your favorite TV shows, movies, music, or podcasts ahead of time, and consider bringing a book to keep yourself engaged. 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 get to the airport at least 1.5 to 2 hours before your departure, taking traffic and security lines into account.
• 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, usually 24–48 hours before your flight. Some airlines may permit seat selection even earlier.
• Arrive at the airport in plenty of time—make sure to arrive at the airport at least 3 hours before departure for international flights to accommodate check-in, security, and immigration processes.
• Relax at the airport—if you have some extra time, take the opportunity to browse the shops, grab a coffee, or unwind at the gate or in a departure lounge if you have access. Airport Wi-Fi is generally free and available.
• Adjust to the new time zone mid-flight—begin synchronizing your body clock by changing your watch and 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

January 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 $96, while one-way tickets start from from $44. 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, Allegiant Air, Delta, American Airlines, Southwest Airlines, United, JetBlue Airways 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.