7 Cheapest Places to Fly to From Boston (Right Now)

by Global Viewpoint
7 Cheapest places to fly to from Boston

Are you looking for the cheapest places to fly to from Boston right now? Maybe you’re looking for a new and exotic international vacation destination with affordable flights from Logan International Airport. Or maybe you want to seize the opportunity for a cheap flight within the US. Either way, you’re in luck! I am very familiar with finding the best deals out of my home state, and I’m sharing this information with you. 

If you’re from Boston, I don’t have to tell you that it’s a great city. It’s bursting with rich American history, delicious food, and many popular attractions. There’s no real reason to leave. But as a world traveler, I know that there is so much more to explore throughout the world. When the travel bug bites, it’s best to fly!

It’s no secret that Boston is not the most affordable place to live. And it’s even less of a surprise to learn that travel can get expensive. There is some good news, though. There are many cheap flights from Boston that can take you to some incredible places on a budget. You just need to do some research and open your plans to a little flexibility. With a little patience, you’ll find the ideal escape from Beantown in no time (and, best yet: on a budget!). 

Whether you’re from Boston city proper, the Boston metropolitan area, or within easy access to Logan International Airport, you will love these cheap flights from Boston in 2023. 

Without further ado, here are some of the cheapest places to fly to from Boston.

cheapest places to fly from Boston text overlay over a cloud background with an airplane wing
This article on the cheapest places to fly to from Boston contains affiliate links, where I may receive a commission at no extra cost to you.

My #1 tip for finding cheap flights out of Boston 

Looking for the cheapest flights from Boston? Before we look at some of the most budget-friendly destinations, I want to tell you a little secret. This is the key to finding the cheapest flights and saving money on airfare. 

For the past 3 years, I’ve been using Scott’s Cheap Flights (now called Going) to find the cheapest flight deals worldwide. You can find cheap places to fly to from Boston, NYC, or wherever you depart. All you have to do is enter your home airport (such as BOS, JFK, ATL, etc.) and your destination. They will then send you mistake fares and cheap flight deals you’ll only think are too good to be true. 

In 2022 alone, I saved thousands of dollars thanks to their email alerts. This includes, most recently, a $225 roundtrip fare from Boston to Barcelona. Typically, I save about $300 roundtrip whenever I fly.

If you’re a frequent traveler, consider upgrading to their premium version. It costs $49 per year, but it will easily save you hundreds (or thousands) of dollars if you fly just 2-3 times. I recommend signing up for the free trial (which you can cancel at any time) to test it out for yourself. And if you find it valuable, use my coupon code JON20 to save 20%!

Other considerations when looking for the cheapest places to fly to from Boston

The world is vast, with over 40,000 commercial airports. To find a reasonable amount of cheap destinations from Boston, I limited my focus to major airports in North America, South America, and Europe. While you can find flight deals to other continents, you will find the cheapest, most accessible flights from Boston listed below. 

It’s important to note that flights from Boston can and will vary throughout the year. Ticket prices are subject to supply and demand, so you can expect to pay higher fares during peak travel times. For instance, December is an expensive time to fly to Hawaii because it’s high season. Flights to Florida will similarly be more expensive in the winter. On the other hand, you’ll likely find the opposite is true for flights to Europe. When planning a European adventure on a budget, you’re better off visiting between January and April during the off-season. 

While the cheapest flights from Boston may vary in exact price, overall, the cheapest destinations will remain relatively the same. Some places will always be cheaper to fly to, and some will always be more expensive, regardless of the season. 

For this article, I have not included any cheap destinations from Boston that are within easy driving distance. Sure, you can find inexpensive flights to cities like NYC, Philadelphia, and Providence, but we’re looking beyond New England and nearby cities on the East Coast

From domestic to international flights, here are the 7 cheapest places to fly to from Boston in 2023. 

Looking to save BIG on airfare? I recommend signing up for the free version of Dollar Flight Club. Thanks to DFC, I’ve saved THOUSANDS of dollars…so I couldn’t recommend it more!

Cheapest Places to Fly from Boston in 2023: Cities with Cheap Flight Deals

Below are the cheapest flights from Boston across the US and world:

1. Boston to Orlando, FL ($97 roundtrip)

Looking for cheap flights from Boston? Orlando, Florida, checks all boxes when planning a vacation. It is one of the cheapest places to travel to from Boston and offers many recreation and adventure opportunities. 

Orlando is one of the cheapest places to fly to from Boston
Orlando is one of the world’s most visitor-friendly cities.

There are four airports in and around Orlando, but if you’re looking for cheap airfare, your best bet is the Orlando International Airport (MCO). Just six miles from Downtown Orlando, MCO is the busiest airport in Florida and the seventh busiest in the country. This means it’s easy to find good flight deals and transportation options. 

Orlando is one of the best destinations for a cheap flight from Boston

Families and solo travelers will find so much to do and see in Orlando. You can make the most of a visit to the world’s theme park capital by visiting Disney World, Universal Studios, and SeaWorld. Are you fascinated by science and space? You’ll love visiting the Kennedy Space Center, where you can learn more about NASA. For a truly mind-bending experience, check out the Museum of Illusions at ICON Park.

There is more to O-Town than amusement parks and indoor recreation. If you want to enjoy the beautiful Florida sunshine, you can kayak Rock Springs at Kelly Park or challenge your body at Orlando Tree Trek Adventure Park in Kissimmee. While Orlando is 60 miles away from its closest beach, there is still plenty to do on land and at nearby lakes. If you want to hit up the coast, Cocoa Beach is only an hour away!

Disney World is one of the most popular destinations in Orlando
Walt Disney World Resort includes 4 theme parks, 2 water parks and over 20 Resort hotels.

Spring is a good time to travel for the cheapest flights from Boston to Orlando. The months between March and May give you a good balance of cheap airfare and lovely weather. January and February are also cheap months to fly from Boston to Orlando after the holiday rush has passed. 

2. Boston to St. Thomas, Virgin Islands ($217 roundtrip)

Looking for cheap flights from Boston? Why not give the Virgin Islands a chance? Specifically St. Thomas. St. Thomas is one of the most popular cruise destinations in the Caribbean. It also happens to be one the cheapest places to fly to from Boston.

St. Thomas, Virgin Islands, is one of the cheapest places to fly to from Boston
St. Thomas is the gateway isle of the U.S. Virgin Islands in the Caribbean.

You can expect a direct flight from Boston to St. Thomas to take about four hours, giving you enough time to watch Titanic or take a nap. American Airlines, Delta, JetBlue, Spirit, and United all offer direct flights to St. Thomas. The island only has one public airport, Cyril E. King Airport (STT), on the southwestern side of St. Thomas. 

Once you arrive, hotel staff can pick you up, or you can take a taxi to your destination, such as one of the many all-inclusive resorts. For a relaxing getaway, St. Thomas is known for its white sand beaches, such as Magens Bay Beach, one of St. Thomas’s most photographed locations. This protected cove has calm, clear water and a nearby bar and grill with live music. The Phantasea Tropical Botanical Garden is a unique eco-attraction on the island with lush foliage, colorful Caribbean flowers, and retail orchids and air plants for sale. 

St. Thomas is known for its white sand beaches and crystal clear water
St. Thomas is known for its pristine beaches, snorkeling, and historic buildings.

Other popular things to do on St.Thomas include visiting the Pirates Treasure Museum, the Virgin Islands Children’s Museum, and shopping at St. John Brewers on the Waterfront. To enjoy these great attractions on a budget, I recommend flying to the Virgin Islands between March and June. This is when you can avoid crowds and peak rates while still enjoying pleasant weather.

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3. Boston to Frankfurt, Germany ($399 roundtrip)

When looking for cheap international flights from Boston, look to Frankfurt! Frankfurt, Germany, is a vibrant and cosmopolitan city that offers visitors a wide range of attractions and activities. A nonstop flight from Boston will take about seven and a half hours. Flight prices from Boston to Frankfurt will vary depending on the time of year, but you can find roundtrip flights under $400 if you know how to find a good deal. 

Frankfurt, Germany, is one of the cheapest places to fly to from Boston
Frankfurt, Germany, officially Frankfurt am Main is a beautiful and modern city.

For the cheapest flights to Frankfurt, you’ll fly into the Frankfurt Airport (FRA), or Flughafen Frankfurt, if you want to speak the language. Some airlines offering cheap flights from Boston to Frankfurt include United, Air Canada, Lufthansa, American Airlines, Virgin Atlantic, and Delta. The Frankfurt Airport is only 15 km from the city’s downtown district (about 9 miles). With the electric trains, it’s only a 10-15 minute ride, so renting a car is not necessary. 

Enjoy Frankfurt’s rich history

There is no shortage of things to do once you arrive in this bustling city. Whether you are interested in history, art, nature, or just soaking up the local culture, there is something for everyone here. I recommend exploring the Römerberg, the historic city center of Frankfurt, with its charming half-timbered buildings and cobblestone streets.

 Römerbergis the the historic city center of Frankfurt, Germany.
Statue of Lady Justice in Frankfurt, Germany.

For an unobstructed view of the city, visit the Main Tower. This 56-story skyscraper offers panoramic views of the city from its observation deck. For art fans, the Städel Museum, officially the Städelsches Kunstinstitut und Städtische Galerie, is one of the most important art museums in Germany. It has a collection that spans 700 years of European art. For a scenic stroll, check out the Palm Garde. This beautiful park has a wide variety of tropical and subtropical plants and a greenhouse with exotic flora.

4. Boston to Nashville, TN ($158 roundtrip)

Cheapest flights from Boston come in all shapes and sizes, and this one is among the best!

Are you a music lover looking to experience the charm of the south? You’ll love taking a trip to Nashville, Tennessee. Nashville is a vibrant city with a rich cultural heritage and a thriving music scene. It’s also one of the cheapest places to fly to from Boston. This lively bucket list city is well-known for its music scene, delicious southern cuisine, and friendly locals. 

Nashville, Tennessee is one of the cheapest places to fly to from Boston
A view of Nashville’s waterfront district along the Cumberland River.

The Nashville International Airport (BNA) is a popular destination for budget-friendly airlines like Southwest and Frontier, so you can always find flight discounts. Some months are cheaper to fly than others. If you’re looking for the best deal, consider booking a flight for February, which is usually the cheapest time to fly to Nashville. For the nicest weather, spring is a wonderful time to visit Music City.

Nashville, TN, is a music-lover’s paradise

Nashville Airport is less than 10 miles from downtown, so you can easily take public transportation or use a ride-share service to your hotel or Airbnb. Whether you’re looking to party or spend a relaxing vacation in Nashville, there is something for everyone to enjoy. The Country Music Hall of Fame and Museum is a must for country music fans. Music and history lovers alike will enjoy exploring the historic Ryman Auditorium. The Ryman, once the home of the Grand Ole Opry, is one of the most iconic concert venues and tourist attractions. 

Boadway in Nashville is popular for its bars, honky-tonks, and live music
The Broadway Historic district in Nashville is known for music-related businesses and tourist attractions.

When you’re in town, stroll down Broadway, a bustling street lined with honky-tonks, bars, and live music. For a more down-to-earth way to spend an afternoon, Cheekwood Estate & Gardens is a historic estate with beautiful gardens, art galleries, and a mansion with tours. Everyone can find plenty of ways to pass the time after taking a cheap flight from Boston to Nashville. 

5. Boston to Dublin, Ireland ($376 roundtrip)

Looking for a cheap international flight from Boston to Europe? Check out Dublin! Dublin, Ireland, is a wonderful city to visit, steeped in history, culture, and a vibrant atmosphere. It’s a popular destination for visitors worldwide, but especially from Boston, thanks to great flight deals from sites like Going

Dublin, ireland is one of the cheapest placers to fly to from Boston
Dublin Castle is one of the most important historical buildings in Ireland.

Travelers visiting Dublin will fly into Dublin Airport (DUB), the busiest airport in Ireland. Many airlines offer direct flights to The Pale, including Aer Lingus, British Airways, United, JetBlue, Air Canada, and Lufthansa. Because Dublin is such a busy airport with many airlines, it’s easy to find cheap flights from Boston. Of course, some months are naturally more expensive than others. From my experience of touring Ireland, March is the cheapest month for airfare. 

Dublin has so much to offer

Ireland’s western coast has the city of Galway and a sprawling green countryside, and the east has Dublin with historic tours, good beer, and modern art. No visit to the Emerald Isle is complete without a tour of the Guinness Storehouse. The Guinness Storehouse is the home of the famous Irish stout, and it offers visitors a fascinating look at this iconic drink’s history and brewing process. If you prefer Irish whiskey, take a tour of Teeling Whiskey and learn about the distilling process with a tasting. 

the historic Temple Bar neighborhood is one of the most popular destinations in Dublin.
The famous Temple Bar Pub in central Dublin, Ireland.

For history with a modern flair, the historic Temple Bar neighborhood is one of the most popular destinations in Dublin. This neighborhood is famous for its pubs, restaurants, and cultural attractions. Trinity College is one of Ireland’s oldest universities and is home to the famous Book of Kells, a 9th-century manuscript considered one of Ireland’s greatest cultural treasures. This wonderful historic city has so many other treasures for everyone to enjoy. 

6. Boston to Chicago, Illinois ($167 roundtrip)

There’s a lot to love about Chicago beyond finding cheap flights from Boston (although that’s certainly a plus!). Six airports serve the Windy City, including Chicago Midway Airport (MDW) and Chicago O’Hare International Airport (ORD). When flying to Chigaco from Boston, Midway is more convenient to central Chicago and tends to have cheaper flights. O’Hare is a larger and busier airport with more flights and international routes. No matter which airport you fly into, both are well-connected to the city via train, taxi, rideshare, or rental car. 

Chicago, Illinois is one of the cheapest place to fly to from Boston
Take a Chicago River boat tour when visiting the Windy City.

From its remarkable architecture and top-rate museums to its delicious food and baseball scene, this vibrant city has so much to offer. You don’t have to be a Cubs fan or enjoy deep-dish pizza to have a great time in Chicago, although it certainly doesn’t hurt. Everyone can enjoy a ballgame at Wrigley Field, one of the oldest baseball stadiums in the country. 

If you love architecture and unbeatable views, visit the Willis Tower (formerly known as the Sears Tower) for a stunning view of the city from the Skydeck. You can also experience the architecture of the renowned Frank Lloyd Wright at the Robie House, one of his most famous works. It’s also worth checking out the Art Institute of Chicago, Lincoln Park Zoo, and the Millennium Park Outdoor Public Art Walking Tour

Cloud Gate in Chicago's Millennium Park
Cloud Gate public sculpture in Chicago’s Millennium Park

Summertime is the best time to visit Chicago for the warm weather and festival season. However, the cheapest time to fly from Boston to Chicago is in February.  For cheap flights out of Boston, look no further than Chicago!

7. Boston to San Juan, Puerto Rico ($199 roundtrip)

Looking for an affordable tropical destination to visit from Boston? Add San Juan to your bucket list! This vibrant city is rich in cultural history and leisure activities. When you arrive, I recommend you visit Old San Juan. It’s on my list as one of the best places to visit in Puerto Rico. Walk through the historic streets and admire the colonial architecture, including El Morro fort and San Cristobal fort.

San Juan, Puerto Rico  is one of the cheapest place to fly to from Boston
El Morro fort in San Juan, Puerto Rico

Take a cheap flight from Boston to paradise

If you enjoy rum, I recommend touring the famous Bacardi Distillery, where you can learn about the history of rum-making in Puerto Rico. In addition to the local rum, you must sample the local cuisine. San Juan is known for its delicious food, so try some of the local specialties such as arroz con pollo (rice with chicken), mofongo (mashed plantain dish), and Lechon (roast pork).

Looking for a scenic place to spend a day in San Juan? Explore the El Yunque National Forest, the only tropical rainforest in the United States Forest Service! It’s a beautiful destination for hiking, waterfalls, and bird watching. For scenic ocean views, the Paseo de la Princesa is a historic walkway that runs along the bay in Old San Juan. This path offers beautiful views of the city and the ocean.

Old San Juan offers a historic tropical paradise
Old San Juan offers visitors a historical view of paradise.

Whether you’re interested in history, culture, or a tropical escape, there’s something for everyone in this vibrant city. The best part is, you can find cheap flights from Boston to the Luis Muñoz Marin International Airport (SJU). The cheapest time to fly to San Juan is in February. Thanks to the tropical climate, temperatures range from the low-70s to mid-80s all year long. This means there’s never a bad time to visit this wonderful city. 

Frequently asked questions (FAQs) about flying from Boston on a budget

Here are some of the most common questions I receive about finding the cheapest places to fly to from Boston worldwide. Note that there are many more cheap destinations from Boston, and you can find the occasional rare deals via travel sites. 

Where in Europe is cheapest to fly from Boston?

Curious about cheap international flights from Boston? If you’re dreaming of cobblestone streets, historic castles, and delicious pastries, but don’t want to empty your wallet on airfare, I’ve got some insider info for you.

When it comes to hopping across the pond from Beantown, one of your most affordable options is often Dublin, Ireland. Why, you ask? Well, Dublin is a major hub for several budget airlines, including Aer Lingus and Ryanair, which often results in competitive prices. Plus, who can resist the charm of the Emerald Isle?

Another budget-friendly option is often Reykjavik, Iceland. With airlines like Icelandair offering affordable flights, you could be soaking in a geothermal hot spring or exploring stunning waterfalls without breaking the bank.

And let’s not forget about Lisbon, Portugal. This sun-soaked city often has great deals on flights from Boston, and with its delicious food, historic sites, and beautiful beaches, it’s a destination that offers a lot of bang for your buck.

Kayakson boston harbor
Boston is a great city with so much to offer, including cheap flights from Logan International Airport.

What is the cheapest way to fly out of Boston?

If you’re looking for the best deals out of Boston, you will likely find the best flight deals using Going’s free email service. When you set Logan International Airport as your departure point, you will get notifications year-round for flight deals for destinations around the world. Even if you’re looking to book a traditionally expensive vacation, you can find deals that save you at least 40% off normal prices. 

What tropical island is closest to Boston?

Want to escape the cold and head to a tropical paradise? I don’t blame you! Luckily, Bostonians don’t have to travel too far to reach a slice of paradise.

The closest tropical island to Boston is Bermuda, and let me tell you, it’s a gem! Bermuda is just a quick two-hour flight away, and you’ll be transported to a world of pink sand beaches, crystal-clear waters, and some of the friendliest people you’ll ever meet.

But wait, there’s more! Not only is Bermuda a tropical paradise, but it’s also a hub for adventure. From snorkeling and scuba diving to kayaking and exploring the island’s underground caves, there’s something for everyone on this magical island.

So pack your swimsuit and sunscreen, and get ready to escape to Bermuda, the closest tropical island to Boston. You won’t be disappointed!

Read next: Top 50 prettiest islands on Earth

What is the cheapest day to fly from Boston?

Generally, the cheapest days to fly out of Logan Internation Airport are Tuesday, Wednesday, and Saturday. These are the slowest travel days during the week, resulting in an average savings of 12-20% without considering other discounts. Airlines want to encourage travelers to buy tickets on their off-peak days. Therefore, they offer reduced prices. 

By contrast, Thursday, Friday, Sunday, and Monday are typically more expensive days to fly. If you can be flexible with your travel arrangements, try to fly out on one of these slower days and see if ticket prices are cheaper. 

You can find cheap flights from Boston using travel websites like Going
George Washington statue in Boston Common Park.

Oh, Boston Logan International Airport, the launching pad for adventures and the gateway to fun. So, where do Bostonians jet off to the most, you ask? Here are some of the most popular places to fly from Boston.

First up, we have the City of Angels, Los Angeles! That’s right; Angelenos and Bostonians have a lot in common: great seafood, passionate sports fans, and a love for sunshine. So, it’s no wonder LA is a hot spot for Bostonians looking to trade clam chowder for tacos and palm trees.

Next up, the Windy City, Chicago! Whether you’re in the mood for deep-dish pizza or a stroll down the Magnificent Mile, Bostonians just can’t resist the charm of the Second City.

And last but not least, we have the Sunshine State, Florida! With its beautiful beaches, warm weather, and theme parks galore, Florida is the ultimate escape for Bostonians looking to thaw out during those chilly winters.

So there you have it, folks, the most popular places to fly to from Boston Logan International Airport! Bon voyage!

What is the best way to save money on flights from Boston?

My biggest advice for finding the best flight deals from Boston is patience and flexibility. Flight deals are never guaranteed, and if your main goal is to find the cheapest flight possible, you may need to wait a bit for the right flight deal to hit your inbox

You must also be a little more flexible when booking flights from Boston. Flying during the off-season or on a weekday instead of the weekend can save you a lot of money. Sometimes it’s as simple as flying on a Tuesday instead of a Sunday. If you’re booking a hotel or rental cabin, you might save money on your accommodations if you stay during the week. 

When looking for the cheapest flight deals, it’s also important to compare the prices of different airlines and to look at flights with layovers. Direct flights are generally more expensive, so if you don’t mind your journey taking longer, consider booking a cheaper ticket that includes a layover or two. 

As mentioned, it’s also important to sign up for alerts from travel websites and airlines, as they will often notify you of sales and special deals. This will help you find the cheapest places to fly to from Boston at any time of year!

Where is the longest flight from Boston?

Get ready to buckle up and settle in, because the longest flight from Boston Logan International Airport is a doozy! Drumroll, please…the longest flight from Boston is to Hong Kong, a bustling metropolis on the other side of the world.

The flight covers a whopping 7,805 miles and takes around 16 hours and 45 minutes, which is plenty of time to catch up on movies, podcasts, and some well-deserved shut-eye.

But don’t worry, the flight isn’t all about cramped seats and stale pretzels. With award-winning in-flight entertainment, gourmet cuisine, and luxurious amenities, flying to Hong Kong can be a comfortable and enjoyable experience.

So, if you’re up for an adventure and ready to explore a new culture, book your ticket to Hong Kong, the destination of the longest flight from Boston. Just be sure to stretch your legs and stay hydrated!

For more travel tips (and inspo), follow my adventures on Instagram: @Global.Viewpoint. Happy Travels! -Jon

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