$33 Cheap Flights to Chatham, MA

View $33 flight on Sun, May 10, 2026Opens in a new window

Popular airlines to Chatham

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How much is the cheapest flight to Chatham?

Prices were available within the past 7 days and start at $33 for one-way flights and $66 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sun, May 10 - Tue, May 19
MCO
Orlando
BOS
Boston
$66 Roundtrip, just found
$66
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, May 10 from Orlando to Boston, returning Tue, May 19, priced at $66 just found
Spirit Airlines
Sat, May 23 - Wed, May 27
MCO
Orlando
BOS
Boston
$106 Roundtrip, just found
$106
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, May 23 from Orlando to Boston, returning Wed, May 27, priced at $106 just found
Breeze Airways
Thu, Sep 3 - Sun, Sep 6
RDU
Raleigh
PSM
Portsmouth
$107 Roundtrip, found 9 hours ago
$107
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, Sep 3 from Raleigh to Portsmouth, returning Sun, Sep 6, priced at $107 found 9 hours ago
American Airlines
Thu, May 21 - Mon, May 25
MCO
Orlando
BOS
Boston
$197 Roundtrip, just found
$197
Roundtrip
just found
Select American Airlines flight, departing Thu, May 21 from Orlando to Boston, returning Mon, May 25, priced at $197 just found
Delta
Fri, May 22 - Sun, May 24
RSW
Fort Myers
BOS
Boston
$197 Roundtrip, just found
$197
Roundtrip
just found
Select Delta flight, departing Fri, May 22 from Fort Myers to Boston, returning Sun, May 24, priced at $197 just found

Frequently asked questions

What month is the cheapest to fly to Chatham?
May is the cheapest month to fly to Chatham. There's less demand then, so fares are usually more affordable. Planning your trip outside of public and school holidays can also help you save.
Which US cities have the cheapest flights to Chatham?
Typically, New York, Washington and Chicago have cheap flights to Chatham. However, being flexible is always key to getting the best prices. Plan your escape midweek or during the low season to keep costs down.
Which US cities fly direct to Chatham?
There are 67 US destinations where you can fly to Chatham directly from. Compare your options by using the "Direct flights only" box on Expedia and find the best departure point for you. Here are some of the major cities to set off from:

  • New York
  • Washington
  • Chicago
  • Philadelphia
  • Charlotte

How to find a cheap flight to Chatham?
Book early or look for cheap flights to Chatham during the off-season, such as January and February. Leaving on a Thursday could also save you 16% on average compared to a Sunday flight.* The Expedia app makes it even easier to know exactly when to book. Just turn on the toggle for "Watch prices" and you'll receive a notification when fares go down.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Chatham?
You can find awesome deals on last-minute flights to Chatham, especially if your travel plans aren't set in stone. Consider jetting out of a different airport, tweaking your trip dates or picking another carrier to get a cheap flight to Chatham.
How far in advance should I book a flight to Chatham?
Secure the departure dates you want and a price that suits your budget by booking your domestic flight to Chatham up to 28 days in advance. Search for tickets between two and four months ahead if you're headed to Chatham from an international destination.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Chatham?
Sundays are usually the best day to book a cheap flight to Chatham, with savings of around 8% on average compared to Fridays. If you purchase tickets on a Friday, expect to pay a higher price as this is often the most expensive day.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Chatham?
Chatham is connected to 5 airports worldwide through 2 carriers, like Cape Air. Nantucket Memorial Airport (ACK) is the main hub for many airlines to Chatham. Tradewind Aviation can also fly you to this destination.
Where do you fly into Chatham?
The main airport when you fly to Chatham is Barnstable Municipal Airport (HYA), but there are some good nearby alternatives like Nantucket Memorial Airport (ACK) and Provincetown Municipal Airport (PVC). You can also touch down at Martha's Vineyard Airport (MVY) and Falmouth, MA (FMH-Otis Air National Guard Base) when flying to Chatham.
How far is the airport from central Chatham?
Touching down at Barnstable Municipal Airport (HYA) puts you about 17 mi west of the center of Chatham.
Can I save money by booking a Chatham trip package?
Bundle your hotel and flight and you could save hundreds of dollars. Plus, you can add extras like car rentals and tours to your Chatham flight and hotel package deal. With Expedia, it's simple to organize all your Chatham travel plans in the same place.
Can I change or cancel my flight to Chatham?
If you reserved your flight to Chatham in the last 24 hours, you can typically cancel or change it for free. After that, additional charges may apply depending on the airline's terms of service. To learn more, head to our Customer Service Portal. Keep in mind that some flights are non-refundable, so you may be issued a credit toward a future flight rather than a direct refund. During your search on Expedia, use the "No cancel fee" or "Changes included" filters to see fares with flexible change policies.

*Flight schedules are subject to change.

*Available to One Key members.

 

Travel information

Destination airport
Logan Intl.
Destination airport IATA code
BOS
Destination city name
Boston
Roundtrip price
$66

Trending flights to Chatham

Prices were available within the past 7 days and start at $33 for one-way flights and $66 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, Apr 22 - Wed, Apr 29
JFK
New York
BOS
Boston
$171 Roundtrip, found 6 days ago
$171
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Apr 22 from New York to Boston, returning Wed, Apr 29, priced at $171 found 6 days ago

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