Prices were available within the past 7 days and start at $52 for one-way flights and $106 for roundtrip, for the period specified. Prices and availability are subject to change.
Traveling to Chesapeake is easy—select from a range of full-service or budget airlines, evaluate flight durations, and choose the option that aligns with your financial plan, timetable, and desire to explore the city’s renowned attractions and neighborhoods.
Major airports near Chesapeake: Yeager Airport (CRW), Tri-State Airport (HTS)
Closest airport to Chesapeake: Tri-State Airport, HTS (around 7 miles)
Flights per week: 900+ flights arriving across Chesapeake airports
Number of airlines that fly to Chesapeake: around 5+ carriers
Popular airports near Chesapeake
Chesapeake is a vibrant city perfect for outdoor enthusiasts and adventure seekers. Visitors flock to Chesapeake for its family-friendly attractions, entertainment options, and rich culture. The area is conveniently accessible via two major airports, making travel seamless for all.
Yeager Airport (CRW): Situated in Kanawha County, West Virginia, approximately 47 miles from Chesapeake, this airport handles both domestic and international flights. It connects to over 90 domestic cities and 7 international destinations, with options for travelers to upgrade to first class or premium economy service for enhanced comfort on various airlines, including American Airlines, Delta, and United.
Tri-State Airport (HTS): Found in Wayne County, West Virginia, about 7 miles from Chesapeake, this airport primarily offers domestic flights, linking to more than 20 cities across the United States. American Airlines is the main airline operating at this location, catering to the travel needs of local passengers.
Top routes to Chesapeake
Orlando (MCO) to Chesapeake (HTS/CRW), with one-way airfare from around $60
Houston (IAH/HOU) to Chesapeake (HTS/CRW), with one-way flights starting at around $120
Tampa (TPA) to Chesapeake (HTS/CRW), with one-way airfare from around $55
Newark (EWR) to Chesapeake (CRW), with one-way airfare from around $50
Denver (DEN) to Chesapeake (HTS/CRW), with one-way tickets available from around $110
Cheapest routes to Chesapeake
North Myrtle Beach (MYR) to Chesapeake (CRW), with low-cost one-way tickets from around $45
Newark (EWR) to Chesapeake (CRW), with affordable one-way prices from around $50
Tampa (TPA) to Chesapeake (HTS/CRW), with budget one-way fares from around $55
Orlando (MCO) to Chesapeake (HTS/CRW), with low-cost one-way tickets from around $60
Chicago (ORD) to Chesapeake (HTS/CRW), with budget one-way fares from around $90
*Flight times and fares vary by season and availability and are based on one-way routes
Top airlines with flights to Chesapeake
American Airlines: Operating flights to Tri-State Airport (HTS) and Yeager Airport (CRW), this airline dominates with around 45% of arrivals to Chesapeake. The average one-way fare is roughly $250, with options for premium service including first class on select routes.
Delta: This carrier also services Yeager Airport (CRW), contributing about 31% of arrivals to Chesapeake. Travelers can expect average one-way fares around $270, with premium options that may feature both premium economy and first class, depending on the route.
United: Providing flights to Yeager Airport (CRW), United accounts for approximately 20% of arrivals to Chesapeake. The average fare for a one-way ticket is about $290, with potential availability of first class as a premium cabin option on certain routes.
Breeze: This airline flies into Yeager Airport (CRW) and represents around 4% of arrivals to Chesapeake. Passengers can find average one-way fares at about $100, making it a budget-friendly choice.
Aeromexico: Offering service to Yeager Airport (CRW), Aeromexico has an average one-way fare of approximately $360, providing travelers with another option for reaching Chesapeake.
Best time to fly to Chesapeake
The most popular months for travelers to fly to Chesapeake are February, March, and April, when peak temperatures in Chesapeake can reach up to 55.4°F in April. If you prefer quieter travel, consider November, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 46°F. For better deals, May usually offers the lowest average one-way fare around $238, roughly 11% cheaper than the yearly average. Looking for additional cheaper months to fly? July, August, and November offer average one-way fares roughly ranging from $244 to $259, making them good options for flexible travelers.
Month
Temperature
Precipitation
Cloudiness
Demand
Average one-way Fare
January
33.3°F (0.7°C)
Light Rain
Mostly Cloudy
Average
$295
February
37.0°F (2.8°C)
Light Rain
Mostly Cloudy
Moderately High
$260
March
45.7°F (7.6°C)
Light Rain
Mostly Cloudy
Moderately High
$304
April
55.4°F (13.0°C)
Light Rain
Mostly Sunny
Moderately High
$286
May
64.9°F (18.3°C)
Light Rain
Mostly Sunny
Average
$238
June
72.7°F (22.6°C)
Light Rain
Mostly Sunny
Average
$262
July
76.3°F (24.6°C)
Light Rain
Mostly Sunny
Average
$244
August
74.7°F (23.7°C)
Light Rain
Mostly Sunny
Average
$257
September
68.9°F (20.5°C)
Light Rain
Mostly Sunny
Moderately Low
$264
October
57.7°F (14.3°C)
Light Rain
Mostly Sunny
Average
$266
November
46.0°F (7.8°C)
Light Rain
Mostly Sunny
Moderately Low
$259
December
39.2°F (4.0°C)
Light Rain
Mostly Cloudy
Moderately Low
$291
*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:
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.
Set up price alerts—as an Expedia member you can use Price Tracking to receive notifications when flight prices change.
Bundle and save—book a flight and unlock a hotel deal on Expedia.*
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.
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 Yeager Airport, Charleston Station, a train station, is located about 4.4 miles away by car.
Hotel transfer: Transfers offer a convenient way to reach your hotel in Chesapeake, with private rides that 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
Huntington: Located 0.9 mile drive away from Chesapeake, Huntington offers a vibrant mix of family-friendly activities and outdoor adventures. Visitors can explore educational venues, enjoy entertainment at the Mountain Health Arena, or unwind at the local recreational areas. Notable attractions include Marshall University, a historic college that enriches the cultural experience, and Camden Park Amusement Park, ideal for those seeking thrills. With its combination of history and family fun, Huntington is an excellent day trip destination.
Proctorville: Proctorville is located 4 miles away from Chesapeake and is an inviting spot for families and outdoor enthusiasts. This charming city features scenic parks and shopping centers, making it a great place for relaxation and exploration. Key highlights include Ritter Park, perfect for leisurely strolls, as well as the renowned Marshall University, which adds a cultural touch. Nature lovers will appreciate the nearby national state park, offering a tranquil escape into nature.
Brentwood: Brentwood is located in the area of Chesapeake and serves as a quaint village for those seeking family-oriented activities and cultural experiences. Visitors can enjoy local attractions such as the history museum and theme park, which provide engaging insights into the region's heritage. With proximity to both Marshall University and Mountain Health Arena, Brentwood is a wonderful spot for family outings or cultural exploration. Its welcoming atmosphere makes it a delightful place to unwind during your travels.
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—with budget airlines, traveling with just a carry-on is often the more economical choice. Maximize your space by packing mini toiletries, wearing your bulkiest clothing, and planning your outfits wisely. This strategy also helps you avoid the hassle of waiting 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 charge your devices fully before boarding.
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, taking into account traffic and security lines.
Bring your own snacks and water—pack some snacks and a refillable water bottle to keep hydrated and save on costs at the airport.
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 essential for comfort. Full-service airlines often allow free seat selection once online check-in begins, typically 24–48 hours before your flight. Some airlines may permit seat selection even earlier.
Arrive at the airport in plenty of time—aim to arrive at least 3 hours before departure for international flights to accommodate check-in, security screening, 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. Airport Wi-Fi is generally free and available.
Adjust to the new time zone mid-flight—begin to align your body clock by changing your watch and adapting your sleep schedule to your destination's time zone. Try to sleep or stay awake during the flight according to the local time of your arrival destination 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 $106, while one-way tickets start from from $52. 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
Allegiant Air, American Airlines 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.
Frequently Asked Questions
What month is the cheapest to fly to Chesapeake?
November is the cheapest month to travel to Chesapeake. Demand is lower then, so you're likely to score a great deal. Booking your trip outside of public and school holidays could also help you save.
Which US cities have the cheapest flights to Chesapeake?
Charlotte often has cheap flights to Chesapeake. Remember that fares can vary based on factors like demand, time of year and number of stopovers.
Which US cities fly direct to Chesapeake?
You can fly to Chesapeake without layovers from US destinations like Charlotte and Orlando. Simply select "Direct flights only" when searching for flights to Chesapeake on Expedia. Then, compare your options and choose the most convenient departure for your trip.
How to find a cheap flight to Chesapeake?
Jetting off in the low season and booking ahead of time are two of the best ways to get cheap flights to Chesapeake. Or, consider flying on a Thursday, which, on average, is 16% cheaper than leaving on a Sunday.* Want to be the first to know when fares drop? Simply set up price tracking on the Expedia app to get real-time updates.
*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 Chesapeake?
It's possible to get cheap deals on last-minute departures to Chesapeake, especially if your travel arrangements are flexible. Consider leaving from a different airport, tweaking your trip dates or choosing an alternative carrier to get a cheap flight to Chesapeake.
How far in advance should I book a flight to Chesapeake?
For some of the best deals on domestic journeys, book your flight to Chesapeake 28 days ahead of your travel dates. For international flights, search for your ticket two to four months in advance. This gives you a better chance of getting your preferred departure dates, times and seats.*
*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 Chesapeake?
Sundays are typically the best day to book a cheap flight to Chesapeake, with savings of around 8% on average compared to Fridays. If you choose to 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 Chesapeake?
There are 4 airlines that connect Chesapeake with 5 airports around the globe. The primary gateway to this city is Yeager Airport (CRW). Travel with any of these well-known airlines to Chesapeake:
American Airlines
United Airlines
Delta Air Lines
Breeze Airways
Where do you fly into Chesapeake?
Chesapeake's main gateway is Tri-State Airport (HTS). If you're looking for more nearby options when flying to Chesapeake, check out Yeager Airport (CRW), Portsmouth, OH (PMH-Greater Portsmouth Regional) or Athens, OH (ATO-Ohio University). It's also possible to fly to Chesapeake through Pikeville, KY (PVL-Pike County - Hatcher Field).
How far is the airport from central Chesapeake?
You'll be about 7 mi southwest of central Chesapeake after landing at Tri-State Airport (HTS).
Can I save money by booking a Chesapeake trip package?
Book a Chesapeake flight and hotel package deal on Expedia, and you can enjoy significant savings. It's easy to bundle your accommodations and flights, and you can add activities and car rentals to create your own customized Chesapeake break. Plus, there's nothing like the convenience of booking everything in the same place.
Can I change or cancel my flight to Chesapeake?
If you reserved your flight to Chesapeake within the last 24 hours, you can typically change or cancel it for free. After that, additional costs may apply depending on the airline's terms and conditions. For more information, check out our Customer Service Portal. Remember that some flights are non-refundable, so you may be offered a credit for a future flight in place of a direct refund. During your search on Expedia, use the "Changes included" or "No cancel fee" filters to see fares with flexible change policies.
Prices were available within the past 7 days and start at $52 for one-way flights and $106 for roundtrip, for the period specified. Prices and availability are subject to change.