Cheap flights To Chestnut Hill (BOS) from $30

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Cheap Flights to Chestnut Hill from $30 One Way, $61 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Jun 3 - Wed, Jun 4
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$61 Roundtrip, just found
$61
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Jun 3 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Wed, Jun 4, priced at $61 just found
Thu, May 29 - Tue, Jun 3
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$72 Roundtrip, just found
$72
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 29 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Tue, Jun 3, priced at $72 just found
Sat, May 31 - Sun, Jun 1
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$80 Roundtrip, just found
$80
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, May 31 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Sun, Jun 1, priced at $80 just found
Thu, May 29 - Tue, Jun 3
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$82 Roundtrip, just found
$82
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 29 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Tue, Jun 3, priced at $82 just found
Thu, May 29 - Thu, May 29
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$83 Roundtrip, found 1 hour ago
$83
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Thu, May 29 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Thu, May 29, priced at $83 found 1 hour ago
Wed, Jun 4 - Mon, Jun 23
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$85 Roundtrip, found 16 hours ago
$85
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Wed, Jun 4 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Mon, Jun 23, priced at $85 found 16 hours ago
Tue, May 20 - Wed, Jun 4
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$86 Roundtrip, found 5 hours ago
$86
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Tue, May 20 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Wed, Jun 4, priced at $86 found 5 hours ago
Wed, May 21 - Thu, May 29
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$89 Roundtrip, found 17 hours ago
$89
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Wed, May 21 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Thu, May 29, priced at $89 found 17 hours ago
Thu, May 29 - Sun, Jun 1
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$90 Roundtrip, just found
$90
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 29 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Sun, Jun 1, priced at $90 just found
Tue, May 20 - Thu, May 22
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$91 Roundtrip, found 1 day ago
$91
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, May 20 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Thu, May 22, priced at $91 found 1 day ago

Chestnut Hill Flight Information

Traveling To
Chestnut Hill
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Spirit Airlines
Flight Price
$61
Earliest Departing Flight
Latest Departing Flight

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Chestnut Hill economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hampton Motor Inn
2.0-star property

Hampton Motor Inn

Jun 26 - Jun 27

1 night stay

Orlando (MCO) to Boston (BOS)

Spirit Airlines • Coach

Boston (BOS) to Orlando (MCO)

Frontier Airlines • Coach
per person
found 19 hours ago
Anchorage Inns And Suites
2.5-star property

Anchorage Inns And Suites

Jun 26 - Jun 27

1 night stay

Orlando (MCO) to Boston (BOS)

Spirit Airlines • Coach

Boston (BOS) to Orlando (MCO)

Frontier Airlines • Coach
per person
found 19 hours ago
Even Hotels Manchester Airport by IHG
3.5-star property

Even Hotels Manchester Airport by IHG

Jun 26 - Jun 27

1 night stay

Orlando (MCO) to Boston (BOS)

Spirit Airlines • Coach

Boston (BOS) to Orlando (MCO)

Frontier Airlines • Coach
per person
found 19 hours ago
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Chestnut Hill premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Omni Boston Hotel at the Seaport
4.0-star property

Omni Boston Hotel at the Seaport

9.2/10 Wonderful! (3,329 reviews)

Jun 3 - Jun 6

3 night stay

Orlando (MCO) to Boston (BOS)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 1 day ago
Loved it! Exceeded expectations.

Reviewed on Apr 23, 2025

The Whitney Hotel
4.0-star property

The Whitney Hotel

9.6/10 Exceptional! (384 reviews)

Jun 3 - Jun 6

3 night stay

Orlando (MCO) to Boston (BOS)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 1 day ago
What a gem in Boston! I've been to Boston many times and usually stay closer to the Downtown Crossing area. This time we stayed at the Whitney, choosing to try out that part of town. We loved it! Bigger than a boutique hotel, but small enough to feel intimate. Charles St is a great walking street, and we loved the location. The room was on the ground level (actually partly below ground) but was excellent! Well-appointed room, a good amount of space for Boston, and super professional staff. I'll be back when I come back to Boston

Reviewed on Jul 30, 2024

The Dagny Boston
4.0-star property

The Dagny Boston

9.4/10 Exceptional! (5,574 reviews)

Jun 3 - Jun 6

3 night stay

Orlando (MCO) to Boston (BOS)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 1 day ago
Really nice restaurant on-site. All staff were helpful and friendly.

Reviewed on Apr 28, 2025

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Chestnut Hill

Save more on flights to Chestnut Hill while making top-quality travel arrangements. At Orbitz we provide access to low cost flights, hotel lodgings and other discounts, along with superior customer service and an unbeatable satisfaction guarantee.

Compare And Book Discount Flights to Chestnut Hill

Now it is easier than ever to find a discount Chestnut Hill flight. Orbitz users can compare airfares for both international and domestic flights and can quickly determine the best hotels and car rental companies to use. You may also check out hotel and other reviews along with a number of travel tips, making your visit to an unfamiliar destination enjoyable and hassle-free.

Use Your Mobile Phone To Secure A Low Cost Flight To Chestnut Hill

We now offer free apps for the most commonly used mobile devices. You can use your mobile phone to share relevant information pertaining to your trips, view images of local lodgings and take advantage of hotel and car rental discounts that may be available only to mobile device users.

Boost Your Frequent Flyer Rewards

You even retain your ability to earn frequent flier points and rewards when purchasing your tickets with Orbitz for Chestnut Hill flights. Enter your frequent flyer information into your Orbitz profile to start earning rewards.

You will find that Orbitz is a very low cost, yet very effective travel planner. Free updates via your mobile phone device will help to keep you and all relevant parties informed of important flight updates. With access to unbeatable sales on all travel essentials, Orbitz makes booking an affordable flight to Chestnut Hill a breeze.

Frequently asked questions

Which airlines fly to Chestnut Hill?
With 20 airlines offering services to Logan Intl. Airport (BOS), the gateway to Chestnut Hill, you have loads of choice. Score a fabulous deal among these renowned international carriers waiting to fly you away to this city:

  • JetBlue - 175 flights to Chestnut Hill per month
  • Delta - 158 flights to Chestnut Hill per month
  • Air Canada - 151 flights to Chestnut Hill per month

What is the best airport to fly to in Chestnut Hill?
Logan Intl. Airport (BOS) is the gateway to the city, so the only decision you need to make will be the window seat or the aisle seat. The center of Chestnut Hill is roughly 8 miles away and where many visitors choose to book a hotel.
How much is a flight to Chestnut Hill?
Return flight prices dipped as low as $61 this past week to Chestnut Hill, and increased to a peak of $91. Some lucky jet-setters departing Baltimore (BWI) managed to pick up one-way flights starting from just $30.
How to book the cheapest flight to Chestnut Hill?
Landing cheap flights to Chestnut Hill is as easy as booking with Orbitz. But if you’d like to make sure you’re nabbing the best flight deals around, here are some suggestions to keep your wallet happy:

  • Taking off from or landing at other airports may help you cut costs. Enter your preferred departure and arrival airports. Next, select the ‘Nearby airports’ function below to see what your options are.
  • If you’re flexible with your itinerary, click on the ‘Show flexible dates’ option. You’ll see the flight deals for the days either side of your selected departure. Fares often vary depending on what day of the week it is.
  • You can also use the ‘Show options’ function to filter results for your preferred airline, seating class, nonstop flights and refundable flights. Under ‘Sort & Filter’ to the left, you can even pick the time of day you want to fly.
  • The early bird gets the most impressive deals, so book as soon as you know your travel dates. The most affordable fares go like hotcakes and prices normally climb as the departure date gets closer.
  • Think about combining your hotels, flights and car rentals into a package deal with Orbitz to make your budget go even further.
  • Don’t fly during the busy season if you can. By avoiding school vacations and summer, you can save loads on your airfares.

How long is a flight to Chestnut Hill?
Flight times vary depending on where you’re leaving from. But to give you a clearer picture of the average duration, have a look at these major routes to Chestnut Hill:

  • Washington, DC (DCA-Ronald Reagan Washington National) to Logan Intl. Airport (BOS) - 1 hour and 44 minutes
  • New York, NY (LGA-LaGuardia) to Logan Intl. Airport (BOS) - 1 hour and 34 minutes
  • New York, NY (JFK-John F. Kennedy Intl.) to Logan Intl. Airport (BOS) - 1 hour and 17 minutes

What is the best time to book a flight to Chestnut Hill?
Book in January, February or August for the lowest airfares to Chestnut Hill. Once you’ve located a bargain, lock it in — cheap flights are known to appear and vanish in the click of a mouse.
What day of the week is the cheapest to book a flight to Chestnut Hill?
If you’re after inexpensive airfares to Chestnut Hill, the best days to book are Tuesdays, Wednesdays and Saturdays. With Orbitz (and some good timing!), an unbeatable flight deal will be all yours.
What is the cheapest day of the week to fly to Chestnut Hill?
Look into departing early in the week to score cheap flights to Chestnut Hill. Orbitz data from 2020 shows Monday is generally the most inexpensive day to take off, followed by Tuesday. Saturday was found to have the most expensive airfares. Presumably, this is because most travelers prefer to kick off their break at the end of the week.
What is the cheapest month to fly to Chestnut Hill?
Consider jetting off in August if you’re on a tight budget. Orbitz data shows that this is generally the best month for cheap flights to Chestnut Hill. June is when fares hit their peak.
Which airlines allow free cancellation?
We understand that plans change and flexibility is important. That’s why you can search for flights that have free cancellation and no change fees on Orbitz. Simply click on “Filter by flexible change policies” and we’ll show you fares with more flexibility than a crayon left in the sun!
What do I need for the flight to Chestnut Hill?
Nothing’s more fun than flying to a new destination, but it’s good to be prepared. These handy tips will help get your trip off to a smooth start:

  • Your travel documents are the most important items you’ll need to take on your flight. To avoid any issues at check-in time, make sure that the information on your ticket is the same as on your government-issued photo ID.
  • Make time fly by even quicker on your short flight by packing the right stuff. Think a water bottle, snacks and entertainment. If you want your journey to Chestnut Hill to go nice and quietly, throw some headphones into your bag too.
  • Even if you’re traveling when it’s 100 degrees outside, carry a sweater or hoodie on board with you. Cabins can get a bit chilly!

How many direct flights are there to Chestnut Hill?
Every month, there are 1,287 direct flights to Chestnut Hill. Pick from a range of airline companies, including JetBlue Airways, Delta Air Lines and American Airlines. Other airlines that operate flights to Chestnut Hill nonstop are Cape Air, United Airlines and Southwest Airlines.
How do I get cheap first-class/business deals to Chestnut Hill?
There are ways of booking first or business-class fares to Chestnut Hill that won’t burn through your wallet. Bag a seat in the pointy end of the plane for less with these great tips:

  • Being flexible isn’t just useful in the gym. Have some room to move around your travel dates so you can pick up cheaper airfares when they crop up.
  • Find a low-cost carrier that offers business-class seats. They usually come with more space and a glass of bubbly — and a nicer price.
  • Make the most of your airline’s loyalty scheme and upgrade your seat. Alternatively, you can try bidding for an upgrade in online auctions.

How to get into Chestnut Hill from the airport?
Head for downtown Chestnut Hill with a Logan Intl. Airport (BOS) car rental. There are two providers at Logan Intl. Airport (BOS) — Enterprise and Advantage Rent-A-Car. Once you’ve signed the papers and have the keys in your hand, the city center is a journey of 8 miles to the southwest of BOS. Another option is to take a taxi downtown and rent a vehicle from one of our Chestnut Hill car rentals. Whatever you decide, when you book with Orbitz, you can be sure you’re always getting an amazing deal!

Nearby

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.