$21 Cheap Flights to Chestnut Hill, MA

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Featured airlines

Featured Airlines: American Airlines, United Airlines, Delta, Spirit, JetBlue, Frontier, Air India, Hawaiian Airlines and Qatar Airways

How much is the cheapest flight to Chestnut Hill?

Prices were available within the past 7 days and start at $21 for one-way flights and $41 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Jun 11 - Wed, Jun 12
ORD
O'Hare Intl.
BOS
Logan Intl.
$41 Roundtrip, found 1 hour ago
$41
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Jun 11 from O'Hare Intl. to Logan Intl., returning Wed, Jun 12, priced at $41 found 1 hour ago
Spirit Airlines
Tue, Aug 20 - Tue, Aug 27
ORD
O'Hare Intl.
BOS
Logan Intl.
$52 Roundtrip, just found
$52
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Aug 20 from O'Hare Intl. to Logan Intl., returning Tue, Aug 27, priced at $52 just found
JetBlue Airways
Mon, Jun 24 - Sun, Jun 30
ORD
O'Hare Intl.
BOS
Logan Intl.
$115 Roundtrip, found 2 hours ago
$115
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Mon, Jun 24 from O'Hare Intl. to Logan Intl., returning Sun, Jun 30, priced at $115 found 2 hours ago
Frontier Airlines
Wed, Aug 21 - Thu, Aug 22
ORD
O'Hare Intl.
BOS
Logan Intl.
$126 Roundtrip, found 6 hours ago
$126
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Aug 21 from O'Hare Intl. to Logan Intl., returning Thu, Aug 22, priced at $126 found 6 hours ago
Delta
Sat, Sep 7 - Sat, Sep 7
ORD
O'Hare Intl.
BOS
Logan Intl.
$132 Roundtrip, found 7 hours ago
$132
Roundtrip
found 7 hours ago
Select Delta flight, departing Sat, Sep 7 from O'Hare Intl. to Logan Intl., returning Sat, Sep 7, priced at $132 found 7 hours ago

Find Your Flights to Chestnut Hill BOS

Cheap flights to Chestnut Hill (BOS)

Get started finding a cheap flight to Chestnut Hill 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.

We recommend using the ‘Flexible Dates’ calendar at the top of the page to see the price of plane tickets on the surrounding dates. This allows you to pick the cheapest days to fly if your trip allows flexibility and score cheap flight deals to Chestnut Hill.

Roundtrip prices range from $41 - $132, and one-ways to Chestnut Hill start as low as $21.

Be aware that choosing a non-stop flight can sometimes be more expensive while saving you time. And routes with connections may be available at a cheaper rate.

Airlines that fly to Chestnut Hill (BOS)

You have several options for which airline you choose to travel with to Chestnut Hill. There are 10 airlines flying into BOS: Spirit Airlines, JetBlue Airways, Frontier Airlines, Delta. 

Cheap plane tickets may be available from different airlines at different times and with unique terms. It’s best to understand the details of each airline’s offer before judging its value.

For example, if you plan to check a bag or bring a carry-on, check whether the cheap airfare deal includes a baggage allowance. If not, verify whether the baggage fee is higher than the difference of other airline plane ticket deals offering free checked/carry-on baggage in exchange for a slightly higher airfare. 

Additionally, your preferred frequent flyer membership programs may influence your choice of cheap airline. Expedia allows you to enter your membership numbers during checkout to earn points from your airline and Expedia Rewards—all while getting a great deal and planning all your travel in one online platform.

Find the best deals

At Expedia, we source many flight deals from multiple providers, so you can easily find the best deals that are right for you. A great strategy for getting the best deals can be to make sure you book and travel at the optimal times. Airfare to Chestnut Hill (BOS) varies throughout the year based on seasonal demand. You’ll see the lowest rates for roundtrips to BOS in June and in September for one-ways.

Cancellation & flexibility

To change or cancel eligible flights, go to ‘My Trips’ and navigate to your itinerary. If you booked within the last 24-hours, you might be able to cancel your flight for free. Learn more about flight changes or cancellations from our customer service portal. Some plane tickets are available with no change fees, which you can filter for during your search.

Frequently asked questions

Where can I learn more about changing or canceling my flight to Chestnut Hill?
Most flights are free to cancel within 24 hours of making the reservation. However, some flights are non-refundable, and you may receive a flight credit from the airline to use for a future booking. For more information, please visit our Customer Service Portal.
How do I find cheap flights to Chestnut Hill that have flexible change policies?
It’s as easy as counting to three with Expedia. Firstly, enter your preferred travel dates and click the “Search” button. Second step: Check the “No change fee” box underneath the “Flexible change policies” filter on the left-hand side of your screen. Step 3. Bag your flexible and cheap ticket to Chestnut Hill.
What is the name of Chestnut Hill's airport?
Logan Intl. Airport (BOS) is the only airport near Chestnut Hill.
How far is BOS from central Chestnut Hill?
BOS is 8 mi from central Chestnut Hill, so you’ll have a reasonable commute into the center.
What airport is best to fly into Chestnut Hill?
A flight to Chestnut Hill means coming in to land at Logan Intl. Airport. Disembark the plane, collect your bags and you’ll be 8 mi from the downtown area.
How many airlines fly to Chestnut Hill?
There are 38 air carriers that service Chestnut Hill from 118 worldwide airports.
How many nonstop flights are there to Chestnut Hill?
With roughly 3,327 direct flights each week, you’ll be touching down in Chestnut Hill before you can ask, “Are we there yet?”
Where are the most popular flights to Chestnut Hill departing from?
Travelers frequently set off from New York, Washington and Chicago airports when going to Chestnut Hill.
How long is the flight to Chestnut Hill Airport?
Which airport you depart from determines how much of the in-flight entertainment you’ll get to see. From Washington to Chestnut Hill, the average flight time is 1 hour and 33 minutes. From Queens Village it takes about 1 hour and 18 minutes, and from Chicago it’s 2 hours and 16 minutes.
How to book the cheapest flight to Chestnut Hill?
If you’d like to save some cash on your Chestnut Hill vacation, listen up! As any seasoned traveler will tell you, don’t leave booking until the last minute. Airfares are usually highest just prior to the departure date. Another excellent way to get the best price is to compare all options. If where you’re headed has multiple airports, don’t forget to look into the cost of flying into a less busy terminal. And finally, don’t forget that it’s first in, best dressed. Know what a typical airfare costs and be ready to snap up a ticket as soon as you see a great bargain. The best deals never last long.
How to survive the flight to Chestnut Hill?
Depending on where you’re coming from, your flight to Chestnut Hill could be no sweat at all or it could go on forever. We’ve rounded up some handy hints that will help you start your next unforgettable escape on the right foot.What to pack in your hand luggage:

  • First and foremost, put in your passport, important documents, wallet and daily medications. Next, you’ll need some entertainment to help pass the time. A juicy book and a laptop filled with your favorite shows are good options. If you plan to catch forty winks, a comfy neck pillow and some noise-canceling headphones will also come in handy. Finally, find room for a few toiletry items so you’ll arrive looking fresh and ready to go.

Do not pack the following items in your hand luggage:

  • While the list of restricted items differs between air carriers, the general rule to follow is nothing flammable, sharp or explosive. This includes screwdrivers, pocket knives, spray paint and fireworks. Sporting equipment like ice skates, and objects that could harm other people, such as firearms and swords, won’t be allowed on board either.

What to wear on a flight:

  • The best way to ensure a comfortable flight is often as simple as your choice of clothing. Prepare yourself for varying temperatures by layering up. That way you’ll stay nice and warm if the cabin gets too cold. Shoes like sandals and heels are best left for other occasions. Even though they may be your favorites, opt for flat, closed-toed footwear like sneakers. Your feet will appreciate it.
  • Unfortunately, a risk of flying long distances is developing deep vein thrombosis (DVT), a blood clotting condition caused by extended periods of inactivity. To prevent this from happening, make the most of every opportunity to walk around the cabin and stretch your legs. Compression tights and socks are another great idea to help reduce this risk.

How to get through airport security fast when flying to Chestnut Hill?
As savvy travelers know, the secret is to be well organized before you get to security. That way, you’ll be boarding that plane to Chestnut Hill in a flash. Follow these tips and get your trip off to a flying start:

  • Your boarding pass and travel ID will need to be presented to airport security personnel. Have them easily accessible so you don’t hold up the queue.
  • Next up is the X-ray machine. Empty your pockets and remove anything metal that is likely to set off the scanner’s alarm. This includes things like headphones or earphones, as well as your coat or jacket. They’ll need to be placed on the conveyor belt for screening.
  • All electronic devices, including your laptop and phone, are also required to be scanned separately.
  • Don’t forget to remove gels and liquids from your carry-on bag. They often need to be sent through the X-ray separately. Each item should be in a container no larger than 3.4 ounces (100 milliliters) and everything must fit inside a single quart-size (one liter), clear zip-close bag.
  • Lightweight sneakers are a good footwear choice as you’re less likely to be required to remove them when going through security. Big boots and other heavy shoes are often subjected to additional screening.
  • Avoid taking prohibited items in your carry-on bag. If you have any sharp or pointed objects, put them in your checked baggage. They won’t be allowed in the cabin.

Flights to Chestnut Hill information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Destination city name
Boston
Roundtrip price
$40

Trending flights to Chestnut Hill

Prices were available within the past 7 days and start at $21 for one-way flights and $41 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Jun 11 - Wed, Jun 12
ORD
O'Hare Intl.
BOS
Logan Intl.
$41 Roundtrip, found 1 hour ago
$41
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Jun 11 from O'Hare Intl. to Logan Intl., returning Wed, Jun 12, priced at $41 found 1 hour ago
*Available to One Key members.