$45 Cheap Flights to Medway, MA

Flights to Medway at a glance

Traveling to Medway is easy; you can choose between full-service and budget airlines. Compare flight times and select the option that best fits your budget, schedule, and plans to explore the city's renowned attractions and neighborhoods.

• Major airport near Medway: Logan International Airport (BOS)
• Flights per week: 7,700+ flights arriving at Medway airport
• Number of airlines that fly to Medway: around 75+ carriers

Popular airport near Medway

Medway is a charming city that offers a perfect blend of family-friendly activities, entertainment, and urban getaways. Visitors flock to Medway for its outdoor spaces, cultural experiences, sports events, and family fun. The city is conveniently accessible via a major airport.

• Logan International Airport (BOS): Situated in Suffolk County, Massachusetts, approximately 25 miles from Medway, this airport caters to both domestic and international travelers. It provides connections to around 260 cities within the U.S. and over 315 international destinations. For travelers seeking enhanced travel experiences, options to upgrade to first class, premium economy, or business class seating are available based on the specific routes and airlines. Major airlines operating here include Delta, JetBlue Airways, and American Airlines.

Top routes to Medway

• Los Angeles (LAX) to Medway (BOS), with one-way tickets available from around $100
• Chicago (ORD/MDW) to Medway (BOS), with one-way fares starting at around $50
• Washington (IAD/DCA) to Medway (BOS), with one-way fares starting at around $70
• Orlando (MCO) to Medway (BOS), with one-way fares starting at around $60
• San Francisco (SFO) to Medway (BOS), with one-way tickets available from around $110

Cheapest routes to Medway

• Presque Isle (PQI) to Medway (BOS), with affordable one-way prices from around $40
• Atlanta (ATL) to Medway (BOS), with cheap one-way fares from around $45
• Chicago (ORD/MDW) to Medway (BOS), with cheap one-way fares from around $50
• Syracuse (SYR) to Medway (BOS), with cheap one-way fares from around $50
• Philadelphia (PHL) to Medway (BOS), with budget one-way fares from around $55

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

Top airlines with flights to Medway

• American Airlines: Operating flights to Logan International Airport (BOS), this airline makes up about 25% of arrivals to Medway. The average fare for a one-way ticket is around $400, with premium cabins including premium economy, business, and first class, depending on the route.
• Delta: Also flying into Logan International Airport (BOS), Delta accounts for roughly 23% of arrivals to Medway. The typical one-way fare is approximately $430, and travelers can choose from premium economy, business class, and first class, depending on the selected route.
• JetBlue Airways: Serving Logan International Airport (BOS), JetBlue represents about 17% of arrivals to Medway. One-way fares average around $370, with premium cabin options that may include premium economy and business class, contingent on the route taken.
• United: Flying into Logan International Airport (BOS), United makes up approximately 13% of arrivals to Medway. The average fare for a one-way flight is about $380, featuring premium cabins such as premium economy, business, and first class, based on the route.
• Southwest Airlines: Operating to Logan International Airport (BOS), Southwest Airlines constitutes around 7% of arrivals to Medway. The average cost for a one-way ticket is roughly $250, making it a budget-friendly option for travelers.

Best time to fly to Medway

The most popular months for travelers to fly to Medway are January, March, and April, when peak temperatures in Medway can reach up to 48°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 64.9°F. For better deals, October usually offers the lowest average one-way fare around $224, roughly 8% cheaper than the yearly average. Looking for additional cheaper months to fly? September, November, and December offer average one-way fares of around $230, 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 Medway

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

*For members. Select hotels.

Arriving in Medway

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

• Public transportation: From Logan International Airport, several transport options are easily accessible by car. Airport Station, a metro station, is located about 0.9 miles from the airport, while Chelsea Station, a train station, is about 2.8 miles away. Additionally, Boston Seaport, a seaport, is situated approximately 3.1 miles from the airport, providing convenient access to various travel routes.
• Hotel transfer: Transfers offer a convenient way to reach your hotel in Medway, with private rides that can be arranged in advance.
• Car rental: Renting a car in Medway is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Medway 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 Medway

• Milford: Milford, located 6 miles drive away from Medway, offers a vibrant blend of entertainment and family-friendly activities. Visitors can enjoy live music concerts, explore the shopping mall center, or relax at Hopkinton State Park, a great spot for outdoor adventures. Key attractions include the Xfinity Center, a premier arena for concerts, and Dean College, known for its modern campus. Whether you're seeking an exciting day out or a leisurely family experience, Milford has something to offer for everyone.
• Franklin: Franklin is located 5 miles away from Medway and is a delightful city perfect for family outings and entertainment. With its array of music concerts and educational venues, there's plenty to keep travelers engaged. The city also features a shopping center for retail therapy. Notable points of interest include the Xfinity Center, a hub for live performances, and Dean College, which boasts a contemporary atmosphere. Franklin is an excellent destination for those looking to enjoy city life with a family-friendly twist.
• Foxboro: Foxboro, located 10 miles away from Medway, is a dynamic city renowned for its entertainment and sporting events. Travelers can attend exciting music concerts at the Xfinity Center or visit the Hall at Patriot Place, a captivating museum. The shopping centers provide additional leisure options for visitors. With Wheaton College nearby, the area combines educational experiences with recreational activities. Foxboro is an ideal spot for families and sports enthusiasts alike, making it a vibrant addition to your travel itinerary.

Tips for short-haul flights to Medway

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. Maximize space by using travel-sized toiletries, wearing your bulkiest clothing, and thoughtfully planning your outfits. 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. Download your favorite TV shows, movies, music, or podcasts ahead of time and consider bringing a book to keep yourself entertained. Remember to charge your devices fully before you board.
• Arrive at the airport in plenty of time—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 your favorite snacks and a refillable water bottle to stay hydrated and save money while at the airport.

Tips for long-haul flights to Medway

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

• Select your seat in advance—for longer flights, selecting 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 offer early seat selection before this time frame.
• Arrive at the airport in plenty of time—aim to arrive at the airport 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 extra time, take the opportunity to browse 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 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 minimize jet lag.

Tips to find the cheapest flights to Medway

The cheapest day to fly

Get started finding a cheap flight to Medway 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 Medway. 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 Medway. 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 Medway, 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 Medway

The lowest price for round-trip flights to Medway in 2026 starts from $77, while one-way tickets start from from $45. 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 Medway. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Medway

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

The most affordable airports to fly into

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

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 Medway.

Stopover savings

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