$52 Cheap Flights to Holliston, MA

Flights to Holliston at a glance

Traveling to Holliston is easy—select from a range of full-service and budget airlines, compare flight durations, and choose the best fit for your budget and itinerary as you plan to explore the city's renowned attractions and neighborhoods.

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

Popular airport near Holliston

Holliston is a charming city that offers a delightful mix of outdoor activities, family-friendly attractions, and vibrant cultural experiences, making it perfect for city vacations. Visitors are drawn to its rich culture, sports, entertainment, and scenic outdoor options, with major airports conveniently serving the area.

• Logan International Airport (BOS): Situated in Suffolk County, Massachusetts, approximately 24 miles from Holliston, this airport offers a wide range of domestic and international flights. Passengers can access around 260 domestic cities and over 315 international destinations. For enhanced comfort, options for upgrading to first class, premium economy, and business class seating are available, varying by airline and route. Major airlines operating at Logan include Delta, JetBlue Airways, and American Airlines.

Top routes to Holliston

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

Cheapest routes to Holliston

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

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

Top airlines with flights to Holliston

• American Airlines: This airline operates flights to Logan International Airport (BOS) and is responsible for approximately 25% of arrivals in Holliston. The average one-way ticket costs around $400, with premium service options that may include premium economy, business, and first class based on the route.
• Delta: Also servicing Logan International Airport (BOS), Delta represents nearly 23% of the arrivals to Holliston. Passengers can expect an average one-way fare of about $430, with premium cabin choices that may consist of premium economy, business, and first class, depending on the specific route.
• JetBlue Airways: JetBlue operates to Logan International Airport (BOS), contributing approximately 17% of Holliston's arrivals. The average fare for a one-way trip is roughly $370, offering premium service options that might include premium economy and business class based on the route.
• United: Flying to Logan International Airport (BOS), United accounts for around 13% of the arrivals in Holliston. The average one-way fare is about $380, with premium cabin selections that may include premium economy, business, and first class according to the route.
• Southwest Airlines: This airline serves Logan International Airport (BOS) and is responsible for roughly 7% of arrivals to Holliston. Travelers can find average one-way fares around $250, making it a budget-friendly choice for many passengers.

Best time to fly to Holliston

The most popular months for travelers to fly to Holliston are January, March, and April, when peak temperatures in Holliston can reach up to 47.8°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? November, September, 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 Holliston

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

*For members. Select hotels.

Arriving in Holliston

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

• Public transportation: From Logan International Airport, several key transport options are conveniently 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 approximately 3.1 miles from the airport.
• Hotel transfer: Transfers offer a convenient way to reach your hotel in Holliston, with private rides that can be arranged in advance.
• Car rental: Renting a car in Holliston is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Holliston 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 Holliston

• Milford: Located 6 miles drive away from Holliston, Milford is a vibrant city that offers a blend of entertainment and family-friendly activities. Visitors can enjoy live music at the Xfinity Center or explore educational opportunities at Dean College. For outdoor enthusiasts, Hopkinton State Park provides stunning scenery and adventure. Whether you're looking to shop at a local mall or catch an event at a sports facility, Milford has something to keep everyone engaged.
• Franklin: Franklin is located 7 miles away from Holliston and serves as a fantastic destination for families and city explorers alike. The Xfinity Center hosts a variety of music concerts, while Dean College offers a modern educational experience. History buffs will appreciate Brown University, a historic institution that adds cultural depth to your visit. With shopping centers and entertainment options, Franklin is perfect for a fun-filled day out.
• Foxboro: Situated 12 miles away from Holliston, Foxboro is known for its sports and entertainment scene. The Xfinity Center is a prime spot for concerts, while Hall at Patriot Place offers a unique museum experience. For those interested in education, Wheaton College is nearby, providing a glimpse into academic life. With shopping centers and beaches close by, Foxboro is an ideal place for family outings or a leisurely day of exploration.

Tips for short-haul flights to Holliston

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 save you money. To maximize space, pack mini toiletries, wear your bulkiest clothing, and plan your outfits efficiently. This approach also allows you to bypass waiting at baggage claim upon arrival.
• Bring your own entertainment—short-haul flights frequently lack in-flight entertainment options. To keep yourself entertained, 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 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 during your airport experience.

Tips for long-haul flights to Holliston

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 provide free seat selection once online check-in opens, which typically occurs 24–48 hours before your flight. Some airlines may allow 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 procedures.
• Relax at the airport—if you have some extra time, take the opportunity to explore 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 either 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 Holliston

The cheapest day to fly

Get started finding a cheap flight to Holliston 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

February is the cheapest month to fly to Holliston. 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 Holliston. 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 Holliston, 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 Holliston

The lowest price for round-trip flights to Holliston in 2026 starts from $92, 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 Holliston. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Holliston

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

The most affordable airports to fly into

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

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 Holliston.

Stopover savings

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