A river with a bridge, marina, and residential area.

$30 Cheap Flights to Chesapeake City, MD

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Popular airlines to Chesapeake City

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Today's featured flight deals to Chesapeake City

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How much is the cheapest flight to Chesapeake City?

Prices were available within the past 7 days and start at $30 for one-way flights and $60 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Avelo Airlines
Frontier Airlines
American Airlines
Southwest Airlines
Delta

What you need to know for your flight to Chesapeake City

Flights to Chesapeake City at a glance

Traveling to Chesapeake City is easy—simply choose between full-service and budget airlines. Compare flight times and costs to find an option that aligns with your budget, schedule, and plans to explore the city's renowned attractions and neighborhoods.

  • Major airports near Chesapeake City: Philadelphia International Airport (PHL), New Castle Airport (ILG)
  • Closest airport to Chesapeake City: New Castle Airport, ILG (around 15 miles)
  • Flights per week: 4,500+ flights arriving across Chesapeake City airports
  • Number of airlines that fly to Chesapeake City: around 45+ carriers

Popular airports near Chesapeake City

Chesapeake City is a delightful destination ideal for outdoor enthusiasts, beach lovers, and those seeking scenic getaways. Travelers flock here for family fun, romantic escapes, and adventurous experiences. The city is conveniently accessible via two major airports.

  • Philadelphia International Airport (PHL): Situated in Philadelphia County, Pennsylvania, approximately 39 miles from Chesapeake City, this airport offers a wide range of domestic and international flights, linking travelers to over 225 domestic cities and more than 160 international destinations. Passengers can opt for upgrades to first class, premium economy, or business class for enhanced comfort, depending on the airline and route. Key airlines operating here include American Airlines, Frontier Airlines, and Delta.
  • New Castle Airport (ILG): Found in New Castle County, Delaware, just around 15 miles from Chesapeake City, this airport provides services for both domestic and international travel, connecting to over 10 domestic cities and 1 international location. Major airlines flying from this airport include American Airlines and Avelo Airlines.

Top routes to Chesapeake City

  • Orlando (MCO) to Chesapeake City (PHL/ILG), with one-way flight options from around $40
  • Boston (BOS) to Chesapeake City (PHL/ILG), with one-way flight options from around $55
  • Fort Lauderdale (FLL) to Chesapeake City (PHL/ILG), with one-way fares starting at around $30
  • Chicago (ORD/MDW) to Chesapeake City (PHL), with one-way flights starting at around $60
  • Atlanta (ATL) to Chesapeake City (PHL/ILG), with one-way flights starting at around $45

Cheapest routes to Chesapeake City

  • Raleigh (RDU) to Chesapeake City (PHL/ILG), with cheap one-way fares from around $30
  • Jacksonville (OAJ/JAX) to Chesapeake City (PHL/ILG), with budget one-way fares from around $30
  • Fort Lauderdale (FLL) to Chesapeake City (PHL/ILG), with affordable one-way prices from around $30
  • Miami (MIA) to Chesapeake City (PHL), with budget one-way fares from around $35
  • Nashville (BNA) to Chesapeake City (PHL/ILG), with low one-way fares from around $35

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

Top airlines with flights to Chesapeake City

  • American Airlines: Serving Philadelphia International Airport (PHL), American Airlines is responsible for roughly 48% of arrivals to Chesapeake City. The typical one-way fare hovers around $290, with premium cabin service options like premium economy, business, and first class varying by route.
  • Delta: Operating flights into Philadelphia International Airport (PHL), Delta accounts for about 13% of arrivals to Chesapeake City. The average cost for a one-way ticket is around $350, offering premium cabin choices, including premium economy, business, and first class depending on the route.
  • Frontier Airlines: Frontier Airlines connects travelers to Philadelphia International Airport (PHL), making up approximately 12% of arrivals to Chesapeake City. The average one-way fare is approximately $160, making it a budget-friendly option for many.
  • Southwest Airlines: Also flying into Philadelphia International Airport (PHL), Southwest Airlines contributes roughly 11% of arrivals to Chesapeake City. Travelers can expect one-way fares averaging around $250, providing a reliable option for reaching the area.
  • United: United operates flights to Philadelphia International Airport (PHL), accounting for about 9% of arrivals in Chesapeake City. The average one-way fare is around $370, with premium cabin services like premium economy and first class available depending on the route.

Best time to fly to Chesapeake City

The most popular months for travelers to fly to Chesapeake City are January, March, and April, when peak temperatures in Chesapeake City can reach up to 53.6°F in April. If you prefer quieter travel, consider October, the least busy time to visit with temperatures around 58.1°F and typically the lowest average one-way fare (around $216), roughly 4% cheaper than the yearly average. Looking for additional cheaper months to fly? May, September, and December offer average one-way fares of around $220, making them good options for flexible travelers.

calendar iconMonthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinesscrowd level iconDemandprice iconAverage one-way Fare
January33.1°F (0.6°C)Light RainMostly SunnyModerately High$247
February35.6°F (2.0°C)Light RainMostly SunnyAverage$225
March43.0°F (6.1°C)Light RainMostly SunnyModerately High$236
April53.6°F (12.0°C)Light RainMostly SunnyModerately High$238
May63.1°F (17.3°C)Light RainMostly SunnyAverage$217
June71.6°F (22.0°C)Light RainMostly SunnyAverage$226
July77.0°F (25.0°C)Light RainMostly SunnyAverage$225
August75.0°F (23.9°C)Light RainMostly SunnyAverage$225
September68.7°F (20.4°C)Light RainMostly SunnyModerately Low$218
October58.1°F (14.5°C)Light RainMostly SunnyModerately Low$216
November46.2°F (7.9°C)Light RainMostly SunnyModerately Low$226
December39.0°F (3.9°C)Light RainMostly SunnyAverage$223

*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 City

Getting some of the best deals on flights to Chesapeake City 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 City 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 City 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 City

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

  • Public transportation: From Philadelphia International Airport, travelers will find PHL Airport Terminals C & D Station, a metro station, just 0.1 miles away by walking, while Philadelphia International Airport Terminal B Station, a train station, is about 0.2 miles away on foot. For those needing maritime transport, Philadelphia Seaport, a seaport, is located approximately 8.4 miles from the airport by car.
  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Chesapeake City, with private rides that can be arranged in advance.
  • Car rental: Renting a car in Chesapeake City is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Chesapeake City 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 Chesapeake City

  • North East: Located 13 miles drive away from Chesapeake City, North East is perfect for those seeking outdoor adventures and scenic beauty. With its inviting beach, visitors can relax by the water or explore the nearby Elk Neck State Park, which offers hiking trails and stunning vistas. The University of Delaware adds a cultural touch with its historic significance, making it an ideal stop for curious travelers. Whether you're interested in motor racing or enjoying a picnic at the bay, North East provides a delightful blend of activities for nature lovers and adventurers alike.
  • Williamsburg: Williamsburg is located 10 miles drive away from Chesapeake City and offers a charming village atmosphere perfect for family outings. Visitors can enjoy a day at Lums Pond State Park, where outdoor activities abound, or catch a performance at the local theater. The proximity of the University of Delaware enriches the area’s cultural landscape, while the urban park provides a lovely space for relaxation. With golf courses and family-friendly attractions, Williamsburg is a great destination for those looking to create lasting memories.
  • Yorkshire: Yorkshire is located 12 miles drive away from Chesapeake City and is an inviting village that combines family-friendly activities with cultural experiences. The historic charm of the University of Delaware and the excitement of the Bob Carpenter Center offer a unique blend of education and entertainment. For those who enjoy nature, the University of Delaware Botanic Gardens presents a beautiful setting for relaxation or a romantic stroll. Additionally, the local shopping centers provide ample opportunities for retail therapy, making Yorkshire a well-rounded stop for visitors.

Tips for short-haul flights to Chesapeake City

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 is often more cost-effective. Maximize space by using travel-sized toiletries, wearing your heaviest clothing, and coordinating outfits efficiently. This approach 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. To keep yourself engaged, download 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, taking into account 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 Chesapeake City

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. Many full-service airlines allow you to select your seat for free once online check-in opens, typically 24–48 hours before your flight. Some airlines may even provide the option to select your seat 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 procedures.
  • Relax at the airport—if you find yourself with 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 readily available.
  • Adjust to the new time zone mid-flight—begin syncing 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 mitigate jet lag.

Frequently asked questions

What month is the cheapest to fly to Chesapeake City?
Plan your trip for September if you want to land a deal on your fare. It's the cheapest month to fly to Chesapeake City. Try to avoid traveling during busy periods such as public holidays or school breaks.
Which US cities have the cheapest flights to Chesapeake City?
Chicago, Atlanta and Boston generally have cheap flights to Chesapeake City. Keep in mind that prices may vary based on factors such as demand, time of year and number of stopovers.
Which US cities fly direct to Chesapeake City?
Take your pick of 77 US cities with direct flights to Chesapeake City. When you book on Expedia, click on "Direct flights only" to compare nonstop routes. Fly to Chesapeake City from any of these leading cities:
  • Chicago
  • Atlanta
  • Boston
  • Orlando
  • Charlotte
How to find a cheap flight to Chesapeake City?
To snag cheap flights to Chesapeake City, book in advance or visit during the off-peak months of April and June. Like another tip? Jet off on a Thursday and save 16% on average compared to traveling on a Sunday.* Set a price alert on the Expedia app and we'll update you 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 Chesapeake City?
It's possible to get great deals on last-minute departures to Chesapeake City, especially if your plans aren't set in stone. Consider flying from a different hub, changing your dates or picking an alternative airline to get a cheap flight to Chesapeake City.
How far in advance should I book a flight to Chesapeake City?
Get the travel dates you want and a price that fits your budget by booking your domestic flight to Chesapeake City up to 28 days in advance. Lock in tickets two to four months ahead if you're traveling to Chesapeake City 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 Chesapeake City?
You can save an average of 8% if you buy tickets on a Sunday instead of Fridays, which tend to be the priciest day to book.* When it comes to snapping up a cheap flight to Chesapeake City, the key is good timing.*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 City?
There are 13 airlines connecting Chesapeake City with 105 airports across the world. The chief entry point to this city is Philadelphia Intl. Airport (PHL). Book a fare with any of these leading airlines to Chesapeake City:
  • American Airlines
  • Delta Air Lines
  • United Airlines
  • Frontier Airlines
Where do you fly into Chesapeake City?
Chesapeake City's main gateway is Philadelphia Intl. Airport (PHL). If you'd like other nearby options when flying to Chesapeake City, check out Lancaster Airport (LNS), Baltimore Washington Intl. Thurgood Marshall Airport (BWI) or Wilmington, DE (ILG-New Castle). It's also possible to fly to Chesapeake City through Aberdeen, MD (APG-Phillips Army Airfield).
How far is the airport from central Chesapeake City?
If you're arriving at Philadelphia Intl. Airport (PHL), you'll be approximately 40 mi northeast of central Chesapeake City.
Can I save money by booking a Chesapeake City trip package?
You could possibly save hundreds of dollars if you choose a Chesapeake City 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 extras like car rentals and tours for your own personalized Chesapeake City break.
Can I change or cancel my flight to Chesapeake City?
If you bought your flight to Chesapeake City within the last 24 hours, you can usually change or cancel it for free. After that, additional charges may apply depending on the airline's terms of service. For more information, visit our Customer Service Portal. Remember that some flights are non-refundable, so you may be issued a credit toward future travel instead of a direct refund. When browsing Expedia, use the "Changes included" or "No cancel fee" filters to find fares with flexible change policies.

*Flight schedules are subject to change.

*Available to One Key members.

Book with confidence

Tips to find the cheapest flights to Chesapeake City

The cheapest day to fly

Get started finding a cheap flight to Chesapeake City 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

September is the cheapest month to fly to Chesapeake City. 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 City. 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 City, 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 City

The lowest price for round-trip flights to Chesapeake City in 2026 starts from from $60, while one-way tickets start from from $30. 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 City. 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 City

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

The most affordable airports to fly into

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

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 City.

Stopover savings

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

Tips to find the cheapest flights to Chesapeake City

Travel information

Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Destination city name
Baltimore
Roundtrip price
$60

Trending flights to Chesapeake City

Prices were available within the past 7 days and start at $30 for one-way flights and $60 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines

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