Cheap Flight Deals to Chatham MA from CA $96

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How to find cheap flights to Chatham?

The cheapest prices found with in the last 7 days for return flights were CA $278 and CA $96 for one-way flights to Chatham for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
CMHBostonMay 23 to May 26CA $278
CMHNantucketMay 13 to May 14CA $1,244
*Prices include taxes and fees

Your guide to flights to Chatham, MA

Spirit Airlines, JetBlue Airways, Porter Airlines fly to Chatham, so use Travelocity to search, find, and compare some truly tempting deals from the 4 airlines—that way you can be sure you’ve found the best deal for you. A flight to Chatham MA currently costs between CA $278 and CA $1,244. Prices vary, but for the best fares, travel in June when prices are at their lowest.  

Top tips for finding cheap flights to Chatham  

The cheapest flight for a round trip to Chatham is currently CA $278. When you search for flights to Chatham, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Chatham for nearby days.  The cheapest month to travel to Chatham is May from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Chatham 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Chatham with Travelocity 

We have top deals on plane tickets even for last minute flights to Chatham, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Chatham for less. 

Find The Perfect Hotel For After Your Flight

Amazing Place to Stay After Flight to Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is CA $517 per night from May 5 to May 6
CA $517
per night
May 5 - May 6
Stay at this luxury resort in Chatham. Enjoy an outdoor pool, a private beach, and a full-service spa. Our guests praise the property condition in our reviews. ...
9/10 Wonderful! (685 reviews)
"Long term homeowner in proximity to CBI and first time guest. Beautiful location and grounds, but stay fell short given established reputation and the cost of accommodations, Room smelled quit musty. Decor suggested a collection of castoff furnishings from perhaps past renovations. Bathroom needed ..."

Reviewed on 1 Apr. 2024

Chatham Bars Inn
The Chatham Motel

The Chatham Motel

2 out of 5
1487 Main Street, Chatham, MA
The price is CA $273 per night from May 13 to May 14
CA $273
per night
May 13 - May 14
Stay at this motel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular attractions Hardings ...
9.2/10 Wonderful! (576 reviews)
"Clean and comfortable rooms."

Reviewed on 18 Sep. 2023

The Chatham Motel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Luxury Hotels in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is CA $517 per night from May 5 to May 6
CA $517
per night
May 5 - May 6
Stay at this luxury resort in Chatham. Enjoy an outdoor pool, a private beach, and a full-service spa. Our guests praise the property condition in our reviews. ...
9/10 Wonderful! (685 reviews)
"Long term homeowner in proximity to CBI and first time guest. Beautiful location and grounds, but stay fell short given established reputation and the cost of accommodations, Room smelled quit musty. Decor suggested a collection of castoff furnishings from perhaps past renovations. Bathroom needed ..."

Reviewed on 1 Apr. 2024

Chatham Bars Inn
The Chatham Motel

The Chatham Motel

2 out of 5
1487 Main Street, Chatham, MA
The price is CA $273 per night from May 13 to May 14
CA $273
per night
May 13 - May 14
Stay at this motel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular attractions Hardings ...
9.2/10 Wonderful! (576 reviews)
"Clean and comfortable rooms."

Reviewed on 18 Sep. 2023

The Chatham Motel
Greyfinch Chatham Inn

Greyfinch Chatham Inn

3 out of 5
946 Main Street (Rte 28), Chatham, MA
The price is CA $239 per night from May 1 to May 2
CA $239
per night
May 1 - May 2
Stay at this 3-star motel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular attractions ...
8.6/10 Excellent! (181 reviews)
Great Place!!
"This hotel was great. We stayed in several places on our New England trip, and Greyfinch was easily the best. It was very nice, clean, and comfortable."

Reviewed on 21 Oct. 2023

Greyfinch Chatham Inn
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Old Harbor Inn

Old Harbor Inn

3.5 out of 5
22 Old Harbor Rd., Chatham, MA
The price is CA $299 per night from May 2 to May 3
CA $299
per night
May 2 - May 3
Stay at this 3.5-star B&B in Chatham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Gallery Antonia and Veterans Field are located nearby. ...
9.6/10 Exceptional! (152 reviews)
"Friendly staff"

Reviewed on 25 Nov. 2023

Old Harbor Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Chatham

The Chatham Motel

The Chatham Motel

2 out of 5
1487 Main Street, Chatham, MA
The price is CA $273 per night from May 13 to May 14
CA $273
per night
May 13 - May 14
Stay at this motel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular attractions Hardings ...
9.2/10 Wonderful! (576 reviews)
"Clean and comfortable rooms."

Reviewed on 18 Sep. 2023

The Chatham Motel
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is CA $517 per night from May 5 to May 6
CA $517
per night
May 5 - May 6
Stay at this luxury resort in Chatham. Enjoy an outdoor pool, a private beach, and a full-service spa. Our guests praise the property condition in our reviews. ...
9/10 Wonderful! (685 reviews)
"Long term homeowner in proximity to CBI and first time guest. Beautiful location and grounds, but stay fell short given established reputation and the cost of accommodations, Room smelled quit musty. Decor suggested a collection of castoff furnishings from perhaps past renovations. Bathroom needed ..."

Reviewed on 1 Apr. 2024

Chatham Bars Inn
Pleasant Bay Village Resort

Pleasant Bay Village Resort

3 out of 5
1191 Orleans Road, Chatham, MA
Stay at this 3-star hotel in Chatham. Enjoy free WiFi, free parking, and breakfast. Popular attractions Caleb Nickerson House and Fox Hill are located nearby. ...
9.6/10 Exceptional! (243 reviews)
"Beautiful grounds and staff that made you feel like family!"

Reviewed on 28 Sep. 2023

Pleasant Bay Village Resort
Save an average of 15% on thousands of hotels when you're signed in
Greyfinch Chatham Inn

Greyfinch Chatham Inn

3 out of 5
946 Main Street (Rte 28), Chatham, MA
The price is CA $239 per night from May 1 to May 2
CA $239
per night
May 1 - May 2
Stay at this 3-star motel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular attractions ...
8.6/10 Excellent! (181 reviews)
Great Place!!
"This hotel was great. We stayed in several places on our New England trip, and Greyfinch was easily the best. It was very nice, clean, and comfortable."

Reviewed on 21 Oct. 2023

Greyfinch Chatham Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Best Chatham Flight and Hotel Packages

Chatham flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Raffles Boston
The Langham, Boston
The Boston Hotel
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Frequently asked questions

Which airlines fly to Chatham?
Being a large travel hub, it’s no surprise that Chatham has 20 airlines that fly in and out of the city. Check out the fares on offer with these top carriers:

  • Delta Air Lines
  • JetBlue Airways
  • American Airlines

Where to stay in Chatham
Finding a great place to stay is a key ingredient for an amazing travel experience. Take your pick of 2,178 properties in Chatham and start cooking up the escape of your dreams!After a long day of exploring, there’s nothing better than returning to a stylish room and a plush bed. The Queen Anne Inn and the Chatham Bars Inn are the top luxury properties to consider in Chatham. However, if you don’t think you’ll spend much time in your suite, how about a cheaper option like the Chatham Highlander Village Inn or the The Hawthorne?
Places to visit in Chatham
0 Like some more options? 0 And that’s not all there is. 0
How to get through airport security fast when traveling to Chatham
Make your journey to Chatham that little bit easier by reading over these handy security tips:

  • Have your boarding pass and passport somewhere accessible. They’ll be the first things you’ll be asked to produce by airport security.
  • Belts, wallets and power banks are to be placed in a tub for X-raying. If you walk into the body scanner with these items, you’ll be requested to turn back and remove them.
  • All laptops must be taken out of their protective carriers and placed in a tray for inspection.
  • Flying with a favorite perfume or cologne? As long as it contains no more than 3.4 ounces (100 milliliters) and it’s stored in a clear resealable plastic bag, you can keep it with you in your carry-on luggage.
  • Hiking boots and other bulky shoes tend to be X-rayed by airport security. We suggest wearing lightweight sneakers instead.
  • The list of non-permissible items is forever changing. Read over your carrier’s website to learn about what is not allowed on board their aircraft.

How to find cheap flights

What is the best day to buy a plane ticket?

Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you’re looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you’re browsing flight deals.

 

What are the cheapest days to fly?

Frequent travellers may already know this, earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.

 

How far in advance can you book a flight?

Here’s the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.

*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

Plane Tickets To Chatham

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Chatham. Browse through our inventory to explore a wide range of cheap flights to Chatham to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Chatham as you anxiously await to exit the plane and explore what Chatham has to offer. Considering all the amazing local food and culture in Chatham, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Chatham to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Chatham without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Chatham with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Chatham today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.