Cheap Flights to Chatham from $59
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How Much Does it Cost To Fly To Chatham?
The cheapest prices found with in the last 7 days for return flights were $91 and $59 for one-way flights to Chatham for the period specified. Prices and availability are subject to change. Additional terms apply
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$91 Roundtrip, found 3 hours ago
$91
Roundtrip
found 3 hours ago
JFK
John F. Kennedy Intl.
BOS
Logan Intl.
$237 Roundtrip, just found
$237
Roundtrip
just found
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | Boston | December 1 to December 8 | $237 |
| BOS | Provincetown | November 11 to November 22 | $240 |
| LGA | Nantucket | September 27 to October 1 | $270 |
| BOS | Nantucket | October 3 to October 9 | $291 |
| MLU | Boston | October 20 to October 27 | $438 |
| FCO | Boston | December 14 to December 21 | $499 |
| FCO | Boston | December 14 to December 21 | $499 |
| JFK | Hyannis | October 1 to October 3 | $517 |
| LIN | Boston | November 21 to November 27 | $545 |
| DCA | Hyannis | September 26 to September 29 | $578 |
| ORD | Nantucket | September 22 to September 26 | $727 |
| JFK | Provincetown | October 22 to October 25 | $728 |
| ORD | Provincetown | October 25 to October 28 | $1,180 |
| SAT | Nantucket | September 20 to September 24 | $1,214 |
| ORD | Hyannis | September 18 to September 20 | $1,542 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| IAD | Boston | September 13 to September 14 | $324 |
| ORD | Boston | September 13 to September 14 | $342 |
| BOS | Hyannis | September 12 to September 14 | $405 |
| EWR | Boston | September 13 to September 17 | $436 |
| JFK | Nantucket | September 12 to September 14 | $472 |
| DCA | Nantucket | September 12 to September 19 | $473 |
| SAT | Boston | September 12 to September 15 | $556 |
| BOS | Nantucket | September 12 to September 12 | $637 |
| FCO | Boston | September 13 to October 22 | $683 |
| FCO | Boston | September 13 to October 22 | $683 |
| JFK | Hyannis | September 12 to September 15 | $703 |
| DCA | Hyannis | September 12 to September 15 | $772 |
| MXP | Boston | September 13 to September 15 | $915 |
| JFK | Provincetown | September 13 to September 16 | $949 |
Chatham Flight Information
Traveling to | Chatham |
|---|---|
Lowest Price | $91 |
Number of Airlines Serving | |
Airlines Serving | Delta, Frontier Airlines, JetBlue Airways |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing Chatham Accommodation Deals
Chatham Bars Inn
297 Shore Rd Chatham MA
$655 nightly
The price is $749 total per night from Sep 24 to Sep 25
$749 total
Sep 24 - Sep 25
Total with taxes and fees
Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
9.2/10 Wonderful! (860 reviews)
"Exceptional"
Reviewed on Sep 9, 2026
The Chatham Motel
1487 Main Street Chatham MA
$219 nightly
The price is $251 total per night from Oct 11 to Oct 12
$251 total
Oct 11 - Oct 12
Total with taxes and fees
Stay at this motel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Gallery Antonia and Hardings Beach are located ...
9.2/10 Wonderful! (639 reviews)
"One night stay was great"
Reviewed on Sep 6, 2026
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
297 Shore Rd Chatham MA
$655 nightly
The price is $749 total per night from Sep 24 to Sep 25
$749 total
Sep 24 - Sep 25
Total with taxes and fees
Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
9.2/10 Wonderful! (860 reviews)
"Exceptional"
Reviewed on Sep 9, 2026
The Chatham Motel
1487 Main Street Chatham MA
$219 nightly
The price is $251 total per night from Oct 11 to Oct 12
$251 total
Oct 11 - Oct 12
Total with taxes and fees
Stay at this motel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Gallery Antonia and Hardings Beach are located ...
9.2/10 Wonderful! (639 reviews)
"One night stay was great"
Reviewed on Sep 6, 2026
Greyfinch Chatham Inn
946 Main Street (Rte 28) Chatham MA
$210 nightly
The price is $240 total per night from Oct 1 to Oct 2
$240 total
Oct 1 - Oct 2
Total with taxes and fees
Book a stay at this family-friendly motel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (281 reviews)
"The property was absolutely charming and the room was spacious and adorable. Great parking and beautiful pool/fire pit area. Bicycles were available for riding around Chatham. We did find a bug in the bathroom which was a little disappointing. Overall, the stay was great and the bed was super ..."
Reviewed on Sep 10, 2026
Save an average of 15% on thousands of hotels when you're signed in
Old Harbor Inn
22 Old Harbor Rd. Chatham MA
$441 nightly
The price is $505 total per night from Sep 20 to Sep 21
$505 total
Sep 20 - Sep 21
Total with taxes and fees
Stay at this B&B in Chatham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chatham Railroad Museum and Veterans Field are located ...
9.6/10 Exceptional! (169 reviews)
"Absolutely loved our stay at the inn! The whole inn is so charming and the staff (including the owners Ray and Judy) were the best!!! They serve breakfast every morning, which was so good and they also had baked goods available all day and it was also phenomenal. We were very impressed how well the ..."
Reviewed on Sep 5, 2026
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
1487 Main Street Chatham MA
$219 nightly
The price is $251 total per night from Oct 11 to Oct 12
$251 total
Oct 11 - Oct 12
Total with taxes and fees
Stay at this motel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Gallery Antonia and Hardings Beach are located ...
9.2/10 Wonderful! (639 reviews)
"One night stay was great"
Reviewed on Sep 6, 2026
Chatham Bars Inn
297 Shore Rd Chatham MA
$655 nightly
The price is $749 total per night from Sep 24 to Sep 25
$749 total
Sep 24 - Sep 25
Total with taxes and fees
Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
9.2/10 Wonderful! (860 reviews)
"Exceptional"
Reviewed on Sep 9, 2026
Pleasant Bay Village Resort
1191 Orleans Road Chatham MA
$215 nightly
The price is $246 total per night from Sep 27 to Sep 28
$246 total
Sep 27 - Sep 28
Total with taxes and fees
Stay at this hotel in Chatham. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
9.6/10 Exceptional! (328 reviews)
"A wonderful place to stay in Chatham. Literally a five minute drive to the pier fish market, Main Street and the beach. Check in was easy and the staff person was very helpful in pointing out places to eat and places to go both in Chatham and nearby Orleans. The room was very clean, spacious and ..."
Reviewed on Aug 30, 2026
Save an average of 15% on thousands of hotels when you're signed in
Greyfinch Chatham Inn
946 Main Street (Rte 28) Chatham MA
$210 nightly
The price is $240 total per night from Oct 1 to Oct 2
$240 total
Oct 1 - Oct 2
Total with taxes and fees
Book a stay at this family-friendly motel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (281 reviews)
Families like: Outdoor pool, close to beach, bicycle rentals
Travelers say...
"The property was absolutely charming and the room was spacious and adorable. Great parking and beautiful pool/fire pit area. Bicycles were available for riding around Chatham. We did find a bug in the bathroom which was a little disappointing. Overall, the stay was great and the bed was super ..."
Reviewed on Sep 10, 2026
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.
Chatham flight + hotel packages - premium economy flights
Price found within the past 48 hours. Click for updated prices.
Chatham flight + hotel packages - first class flights
Price found within the past 48 hours. Click for updated prices.
Need a Car For After Your Flight?
Midsize
East Boston, Massachusetts, USA
$71
$203 total
found 2 days ago
Standard
East Boston, Massachusetts, USA
$72
$207 total
found 2 days ago
Fullsize
East Boston, Massachusetts, USA
$74
$211 total
found 2 days ago
Special
East Boston, Massachusetts, USA
$77
$228 total
found 3 days ago
Lowest prices found within the past 2 days. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
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!
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