8 Affordable Places to Fly From Boston for Your Next Trip

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Ever since I started tracking flight deals from Logan (okay, I might be slightly obsessed), I’ve discovered some absolute steals that’ll make your travel dreams possible. Just last week, I spotted tickets to Lisbon for under $400 roundtrip. Imagine sipping espresso at a sunny cafe in Chiado, then wandering through those gorgeous tiled streets without destroying your savings account.

Looking for some of the best places in Boston to snag cheap flights? From Montreal’s incredible food scene (seriously, get the bagels at St. Viateur) to Nashville’s live music venues, where I spent less on flights than a night out in Back Bay, these 8 destinations prove you don’t need to be rich to travel right. These deals are so good, you might even have money left for lobster rolls when you get back.

#1 tip to find cheap flights from Boston 

Looking for cheap flight deals from Boston? This is a game-changer: Going (formerly Scott’s Cheap Flights).

Here’s the deal: Sign up for free email alerts, set your departure and destination, and boom – you’ll get alerts for insanely cheap flights. Mistake fares? Deep discounts? They’ve got it all.

I’ve saved thousands using Going. Recently, I even found a $299 roundtrip fare from Boston to Paris in May. Not bad!

Want even more deals? Their $49/year premium version is well worth it- just one discounted flight pays for the whole thing. And if you’re into business/first class, you’ll want to sign up for their Elite version, which saved me over $5,000 in 2024 alone. Trust me, it’s a small price for massive savings.

Now, let’s dive into the 8 cheapest destinations from Boston in 2025.

Best Cheap Getaways from Boston

Looking for cheap getaways from Boston? Visit Orlando for world-famous theme parks and entertainment, St. Thomas, Virgin Islands for stunning beaches and island adventures, Azores for breathtaking landscapes and volcanic hot springs, and Frankfurt for historic landmarks and vibrant city life. Whether you’re interested in history, culture, or cuisine, these destinations offer budget-friendly escapes from Boston.

1. Boston to Orlando, FL ($97–$140 roundtrip)

• ✈️ Flight Time: 3-3.5 hours nonstop
• 🛫 Airlines: JetBlue, Spirit, Frontier (best deals often Tuesday-Wednesday)
• 📅 Best Time to Visit: January to early March 🌞 and September to October 🍂 for the best deals
• 🏆 Perfect for: Theme park enthusiasts 🎢, family trips 👨‍👩‍👧‍👦, winter escapees ☀️, budget travelers 💰

Orlando is basically Boston’s favorite winter escape plan that somehow stays affordable despite everyone having the same idea. This place delivers reliable sunshine and endless entertainment options without requiring a second mortgage to visit.

Walt Disney World is the obvious draw, but locals know Universal Studios actually has better rides and shorter lines if you’re past the princess phase. Skip the theme parks entirely? Head to Winter Park for gorgeous gardens and boat tours without a costumed character in sight, or hit Lake Eola Park downtown for local beers and amazing food with actual Orlando residents. Who knew there was life beyond Mickey?

Best time to fly from Boston is January to early March when everyone’s desperate to escape New England winter and airlines respond with serious deals. JetBlue and Frontier constantly battle for this route with fares sometimes dipping below $100 roundtrip.

• Read next: Best Airports Near Orlando
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• For more reading: Things to Do in Orlando at Night
• Keep reading: Best Airlines to Fly to Orlando

2. Boston to St. Thomas, Virgin Islands ($217–$260 roundtrip)

• ✈️ Flight Time: 4.5 hours nonstop
• 🛫 Airlines: JetBlue, American, United, Delta (best deals with JetBlue)
• 📅 Best Time to Visit: April to June 🏝️ and September to November 🍂 for lower prices and good weather
• 🏆 Perfect for: Beach lovers 🏖️, snorkeling enthusiasts 🐠, sailing fans ⛵, tropical cocktail sippers 🍹

St. Thomas is a legit Caribbean paradise you can actually afford. This island gives you those gorgeous beaches and turquoise water without needing to sell a kidney to get there from Boston.

Magens Bay is that beach you see on screensavers but can actually swim at, with powder-white sand and water so clear you’ll think someone Photoshopped it. Charlotte Amalie lets you score duty-free deals on booze and luxury stuff for way less than you’d pay at home. Ferry over to Water Island to snorkel with sea turtles without fighting through tourist crowds, or hit up Mountain Top for banana daiquiris with views so insane even your terrible phone photos will look professional.

JetBlue has the best direct flights from Boston, usually cheapest in May-June or September-October when you dodge both hurricane season and peak tourist prices. 

• Read next: Caribbean Cruise Guide
• You may also like: Top Things to Do in St. Thomas

3. Boston to the Azores ($300 –$340 roundtrip)

• ✈️ Flight Time: 5-5.5 hours nonstop
• 🛫 Airlines: Azores Airlines, TAP Portugal (seasonal direct flights)
• 📅 Best Time to Visit: May to October 🌞 for hiking and outdoor activities
• 🏆 Perfect for: Nature lovers 🌋, hikers 🥾, hot spring enthusiasts ♨️, adventure seekers 🧗‍♀️

The Azores are basically Europe’s best-kept secret that Boston somehow has direct flights to. These Portuguese islands in the middle of the Atlantic are like Hawaii meets Iceland but without the insane prices or crowds.

São Miguel is the main island with crazy volcanic landscapes, neon-blue crater lakes, and hot springs where you can literally cook food in the ground. Ponta Delgada has those charming European vibes with black and white cobblestone streets and amazing seafood for half what you’d pay in Boston. Hike around Sete Cidades to see the famous twin lakes (one blue, one green) that look fake in photos but are even more mind-blowing in person. 

Azores Airlines runs direct flights from Boston, with the best deals in spring and fall when weather’s still perfect but summer crowds are gone. This is one of those rare routes where booking 3-4 months ahead can save you serious cash. 

• Read next: Must-See Places in the Azores

INSIDER TIP: Again, I highly recommend signing up for Going.com (Scott’s Cheap Flights) to find the best deals. Last year, I got an email alert on a $250 roundtrip fare from Boston to Ponta Delgada with TAP. This made it super cheap and easy to get to Europe. The premium version is 100% worth the money, but I would at least sign up for the free version to save big on airfare this year.

4. Boston to Frankfurt, Germany ($399–$440 roundtrip)

• ✈️ Flight Time: 7-7.5 hours nonstop
• 🛫 Airlines: Lufthansa, United, Condor (year-round direct routes)
• 📅 Best Time to Visit: April-May 🌷 and September-October 🍂 for pleasant weather and fewer tourists
• 🏆 Perfect for: City explorers 🏙️, museum lovers 🖼️, beer enthusiasts 🍺, gateway travelers ✈️

Frankfurt is your budget backdoor into Europe that most people totally sleep on. This city isn’t just banks and business travelers; it’s actually the perfect combo of old European charm and modern city vibes, plus it’s the cheapest German destination you can reach from Boston.

Römerberg square looks like it’s straight out of a fairytale, while Kleinmarkthalle food market is where locals crush currywurst and beer before noon without judgment. Grab incredible city views from the Main Tower, then hit Sachsenhausen neighborhood for traditional apple wine taverns where you’ll drink with Germans who’ve been coming to the same spots for decades. 

Lufthansa runs direct flights from Boston daily, with prices dipping lowest in February-March and October-November. Sign up for their newsletter to catch flash sales that sometimes drop fares below $400 roundtrip. 

• Read next: Hidden Gems in Frankfurt

5. Boston to Nashville, TN ($158–$190 roundtrip)

• ✈️ Flight Time: 2.5 hours nonstop
• 🛫 Airlines: JetBlue, Southwest, Delta, American
• 📅 Best Time to Visit: April-May 🌸 and September-October 🍂 for perfect weather and outdoor events
• 🏆 Perfect for: Music lovers 🎸, foodies 🍗, nightlife seekers 🍻, weekend trippers 🌆

Nashville is the South’s coolest city that somehow stays affordable to fly to from Boston. This place has way more personality than most cities twice its size, with live music literally everywhere and food so good you’ll consider relocating.

Broadway is the famous strip packed with honky-tonks where you can bar-hop through live music venues without paying a single cover charge. Skip the tourist traps and head to East Nashville for killer local restaurants, vintage shops, and bars where actual locals hang out. The Gulch neighborhood has that perfect mix of street art, craft breweries, and boutiques that’ll drain your wallet but fill your Instagram. 

JetBlue and Southwest battle for this route with fares often dipping below $170 roundtrip during sales. Avoid CMA Fest in June and peak summer when prices spike.

• Read next: Best Places to Stay in Nashville
• You may also like: Travel Bucket List Ideas
• For more reading: Magical Airbnbs in Tennessee
• Keep reading: Things to Do in Nashville at Night
• Also worth reading: Nashville Family Activities

6. Boston to Dublin, Ireland ($376–$430 roundtrip)

• ✈️ Flight Time: 6-7 hours nonstop
• 🛫 Airlines: Aer Lingus, Delta, United (daily direct flights)
• 📅 Best Time to Visit: April-June 🌷 and September-October 🍂 for fewer tourists and decent weather
• 🏆 Perfect for: Pub enthusiasts 🍺, history buffs 🏰, literary fans 📚, friendly locals 🤝

Dublin is probably the cheapest European city you can fly to from Boston that doesn’t feel like a budget destination. This compact Irish capital delivers serious character, insanely friendly locals, and that perfect mix of history and nightlife without breaking the bank.

Temple Bar is the obvious tourist spot, but walk literally 5 minutes in any direction to find pubs like The Long Hall or Grogan’s where you’ll drink with locals instead of other Americans. Trinity College Library looks fake it’s so beautiful, and the Guinness Storehouse tour includes a pint with the best view in the city. 

Aer Lingus runs the most direct flights and typically has the best deals, especially during their January-February sales. 

• Read next: Best Airlines to Dublin
• You may also like: Cheap Flights from Dublin
• For more reading: Globus Journeys Ireland Tour
• Keep reading: West Ireland Travel Guide
• Also worth reading: Dublin Activities for Young Adults
• Readers also enjoyed: Most Beautiful Places in Dublin
• Don’t miss this: Unique Restaurants in Dublin

7. Boston to Chicago, Illinois ($167–$210 roundtrip)

• ✈️ Flight Time: 2.5-3 hours nonstop
• 🛫 Airlines: United, American, JetBlue, Spirit
• 📅 Best Time to Visit: May-June 🌿 and September-October 🍂 for perfect weather and outdoor events
• 🏆 Perfect for: Architecture fans 🏙️, food lovers 🍕, art enthusiasts 🎨, city explorers 🌆

Chicago is basically a cheaper, friendlier NYC that’s ridiculously easy to reach from Boston. Despite being one of America’s biggest cities, flights stay competitive and affordable year-round thanks to multiple airlines fighting for your dollars.

The Loop gives you that big-city skyline experience with architecture that’ll make you actually stop and look up. Millennium Park has the famous Bean for your obligatory reflection selfie, while the lakefront trail offers 18 miles of views that remind you this isn’t actually an ocean. After a weekend here, you’ll be that annoying person who won’t shut up about how Chicago is actually cooler than New York.

United and American constantly compete on this route with deals regularly dipping below $180 roundtrip, especially for Tuesday and Wednesday departures. Winter is cheapest but honestly brutal (think Boston but windier), while summer sees slightly higher prices during festival season. 

• Read next: Cheapest Flights from Chicago
• You may also like: Unique Restaurants in Chicago
• For more reading: Best Things to Do in Chicago as a Couple
• Keep reading: Things to Do in Chicago at Night
• Also worth reading: Most Beautiful Places in Chicago
• Readers also enjoyed: Best Places to Stay in Chicago

8. Boston to San Juan, Puerto Rico ($199–$230 roundtrip)

• ✈️ Flight Time: 4 hours nonstop
• 🛫 Airlines: JetBlue, Delta, American, United
• 📅 Best Time to Visit: April-June 🌴 and September-November 🍂 for lower prices and good weather
• 🏆 Perfect for: Beach lovers 🏖️, history buffs 🏰, foodie explorers 🍽️, rainforest adventures 🌿

San Juan is tropical paradise without the passport hassle or currency exchange. This place gives you Caribbean vibes with the convenience of staying on U.S. soil, all with direct flights from Boston that cost less than flying to most West Coast cities.

Old San Juan looks like someone dropped a colorful European city onto a Caribbean island, with cobblestone streets and buildings painted in every color imaginable. Condado Beach offers that perfect mix of white sand, clear water, and beachfront bars serving drinks with tiny umbrellas. Just outside the city, El Yunque rainforest lets you hike to waterfalls where you can actually swim, making those sweaty trails completely worth it.

JetBlue usually has the cheapest direct flights, with regular sales in the $180-200 range if you avoid major holidays and spring break. 

• Read next: Budget-Friendly Tropical Destinations
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• For more reading: Best Places to Visit in Puerto Rico

EXPERT ADVICE: If you’re planning to fly to the Caribbean, I HIGHLY recommend signing up for Going.com (Scott’s Cheap Flights) to find the best deals. Recently, I was notified of a $160 roundtrip fare from Boston to Puerto Rico with JetBlue. The premium version is 100% worth the money, but I would at least sign up for the free version to save big on airfare this year. And if business class is more your speed, then you’ll want to upgrade to the Elite Version, where I’ve spent under $1,200 on international flights abroad!

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.

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. 

What are the most popular places to fly to from Boston Logan Intl?

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. And don’t forget to sign up for Scott’s Cheap Flights to get the best possible deal on airfare this year! Happy Travels! -Jon