$40 Cheap Flights to Chesapeake, VA

Flights to Chesapeake at a glance

Traveling to Chesapeake is easy; you can choose between full-service and budget airlines. Compare flight durations and select the best option that fits your budget and itinerary as you plan to discover the city's renowned attractions and charming neighborhoods.

• Major airports near Chesapeake: Norfolk International Airport (ORF), Richmond International Airport (RIC), Newport News - Williamsburg International Airport (PHF)
• Closest airport to Chesapeake: Norfolk International Airport, ORF (around 10 miles)
• Flights per week: 5,100+ flights arriving across Chesapeake airports
• Number of airlines that fly to Chesapeake: around 30+ carriers

Popular airports near Chesapeake

Chesapeake is a vibrant city perfect for family getaways, outdoor adventures, and romantic escapes. Visitors are drawn to its beautiful beaches, rich culture, and family-friendly activities. The city is conveniently accessible through three major airports, including Chesapeake Regional Airport and Chesapeake Norfolk International Airport, offering various options for one-way flights.

• Norfolk International Airport (ORF): Situated in Norfolk City County, Virginia, approximately 10 miles from Chesapeake, this airport offers a range of domestic and international services. With connections to over 195 domestic cities and more than 60 international destinations, travelers have the option to upgrade to first class or premium economy seating for enhanced comfort, depending on the airline and route. Major carriers operating here include American Airlines, Delta, and Southwest Airlines.
• Richmond International Airport (RIC): Located in Henrico County, Virginia, about 77 miles from Chesapeake, this airport caters to both domestic and international flights. It connects travelers to over 180 domestic cities and 65 international destinations, with the option to upgrade to first class or premium economy service for a more comfortable journey, based on the airline and route. American Airlines, Delta, and JetBlue Airways are among the popular airlines serving this airport.
• Newport News - Williamsburg International Airport (PHF): Found in Newport News City County, Virginia, approximately 28 miles from Chesapeake, this airport primarily offers domestic flights to around 25 cities nationwide. American Airlines is the key carrier operating from this airport, providing travelers with reliable service to various destinations across the country.

Top routes to Chesapeake

• Orlando (MCO) to Chesapeake (ORF/PHF/RIC), with one-way fares starting at around $40
• Boston (BOS) to Chesapeake (ORF/PHF/RIC), with one-way flight options from around $75
• New York (JFK/LGA) to Chesapeake (ORF/RIC), with one-way flight options from around $90
• Las Vegas (LAS) to Chesapeake (ORF/RIC), with one-way fares starting at around $110
• Tampa (TPA) to Chesapeake (ORF/PHF/RIC), with one-way fares starting at around $50

Cheapest routes to Chesapeake

• New Haven (HVN) to Chesapeake (ORF/RIC), with low-cost one-way tickets from around $35
• Baltimore (BWI) to Chesapeake (ORF/RIC), with budget one-way fares from around $40
• Orlando (MCO) to Chesapeake (ORF/PHF/RIC), with low one-way fares from around $40
• Atlanta (ATL) to Chesapeake (ORF/PHF/RIC), with affordable one-way prices from around $40
• Hartford (BDL) to Chesapeake (ORF/RIC), with low one-way fares from around $40

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

Top airlines with flights to Chesapeake

• American Airlines: This airline services Norfolk International Airport (ORF), Newport News - Williamsburg International Airport (PHF), and Richmond International Airport (RIC), representing about 38% of Chesapeake's arrivals. The average fare for a one-way ticket is around $280, with possible first-class service depending on the route.
• Delta: Connecting to Norfolk International Airport (ORF) and Richmond International Airport (RIC), Delta accounts for roughly 26% of arrivals in Chesapeake. Average one-way fares are about $290, with premium cabin options that may include premium economy and first class based on specific routes.
• United: Operating flights into Norfolk International Airport (ORF) and Richmond International Airport (RIC), United makes up around 14% of Chesapeake's arrivals. The average fare for a one-way trip hovers around $300, with potential first-class service depending on the route.
• Southwest Airlines: This carrier flies to Norfolk International Airport (ORF) and Richmond International Airport (RIC), contributing to approximately 12% of Chesapeake's arrivals. Travelers can expect an average one-way fare of about $260.
• Breeze: Providing service to Norfolk International Airport (ORF) and Richmond International Airport (RIC), Breeze accounts for nearly 3% of arrivals in Chesapeake. The average one-way fare with this airline is approximately $120.

Best time to fly to Chesapeake

The most popular months for travelers to fly to Chesapeake are January, March, and April, when peak temperatures in Chesapeake can reach up to 58.6°F in April. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 73.6°F and typically the lowest average one-way fare (around $216), roughly 7% cheaper than the yearly average. Looking for additional cheaper months to fly? October, May, and August offer average one-way fares of around $218, 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 Chesapeake

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

*For members. Select hotels.

Arriving in Chesapeake

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

• Public transportation: From Norfolk International Airport, several transportation options are conveniently located a short drive away. Norfolk Seaport, a seaport, is about 4 miles from the airport, while Newtown Road Station, a metro station, is approximately 5.8 miles away by car. If you’re looking to travel by train, Norfolk Station is situated about 7.1 miles from the airport.
• Hotel transfer: Transfers offer a convenient way to reach your hotel in Chesapeake, with options including free hotel shuttles and private rides, which can be arranged in advance.
• Car rental: Renting a car in Chesapeake is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Chesapeake 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 Chesapeake

• Norfolk: Located 6 miles drive away from Chesapeake, Norfolk is a vibrant city that offers a variety of experiences for travelers. Enjoy outdoor activities along the scenic boardwalk or explore shopping centers for unique finds. Key attractions include the Norfolk Botanical Garden, perfect for families and romantic strolls, and the Norfolk Scope, an entertainment venue ideal for family outings. Don’t miss a visit to Old Dominion University, a historic campus that adds cultural depth to your trip.
• Portsmouth: Situated 5 miles drive away from Chesapeake, Portsmouth is another charming city that caters to families and outdoor enthusiasts. Wander along the boardwalk or visit local shopping centers for delightful shopping experiences. Highlights include Town Point Park, where you can enjoy family-friendly activities and beautiful views, as well as the Norfolk Scope for various entertainment options. Old Dominion University, a historic institution, is also nearby, offering cultural insights for visitors.
• South Norfolk: South Norfolk is located around the area of Chesapeake and is known for its inviting beach atmosphere and outdoor activities. Take advantage of the local boardwalk and shopping malls for leisure and retail therapy. This neighborhood is in close proximity to Norfolk State University, which showcases the area's educational heritage, and the Norfolk Scope for family entertainment. The local esplanade and beach area make South Norfolk an appealing spot for those seeking relaxation and family fun.

Tips for short-haul flights to Chesapeake

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, traveling with just a carry-on can often be more cost-effective. Maximize your space by opting for mini toiletries, wearing your heaviest clothing, and coordinating your outfits in advance. This approach also allows you to bypass the wait at baggage claim upon arrival.
• Bring your own entertainment—many short-haul flights may lack in-flight entertainment options. To keep yourself entertained, download your favorite TV shows, movies, music, or podcasts ahead of time, and consider bringing a book as well. Remember to fully charge your devices before you board.
• Arrive at the airport in plenty of time—for all flights, including short or domestic ones, it's advisable to get to the airport at least 1.5 to 2 hours prior to departure, taking into account potential traffic and security lines.
• Bring your own snacks and water—to stay hydrated and save money at the airport, pack some snacks along with a refillable water bottle.

Tips for long-haul flights to Chesapeake

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

• Select your seat in advance—for longer flights, choosing your seat is crucial for comfort. Full-service airlines often allow you to select a seat for free once online check-in opens, typically 24–48 hours before your flight. Some airlines may offer early seat selection options.
• Arrive at the airport in plenty of time—make sure to arrive at least 3 hours prior to 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, grab a coffee, or unwind at the gate or in a departure lounge if you have access. Most airports offer free Wi-Fi for your convenience.
• Adjust to the new time zone mid-flight—begin syncing your body clock by changing your watch and modifying 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 of your arrival to help minimize jet lag.

Tips to find the cheapest flights to Chesapeake

The cheapest day to fly

Get started finding a cheap flight to Chesapeake 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

November is the cheapest month to fly to Chesapeake. 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 Chesapeake. 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 Chesapeake, 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 Chesapeake

The lowest price for round-trip flights to Chesapeake in 2026 starts from $80, while one-way tickets start from from $40. 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 Chesapeake. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Chesapeake

Frontier Airlines, Breeze Airways, Delta, Southwest Airlines, United are just some of the airlines that can typically offer cheap tickets to Chesapeake. 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 Chesapeake and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Chesapeake, 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 Chesapeake. 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 Chesapeake 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 Chesapeake

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 Chesapeake.

Stopover savings

The cheapest tickets to Chesapeake are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Chesapeake. 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 Chesapeake 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 Chesapeake. Simply download the free Expedia app to your smart device and activate Chesapeake 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 Chesapeake. 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.