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 $117 and $59 for one-way flights to Chatham for the period specified. Prices and availability are subject to change. Additional terms apply
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$117 Roundtrip, found 7 hours ago
$117
Roundtrip
found 7 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| SAT | Boston | December 5 to December 19 | $230 |
| BOS | Provincetown | November 5 to November 8 | $240 |
| JFK | Boston | November 19 to November 22 | $255 |
| BOS | Nantucket | January 10 to January 10 | $334 |
| FCO | Boston | January 16 to January 23 | $509 |
| FCO | Boston | January 16 to January 23 | $509 |
| LIN | Boston | November 7 to November 23 | $517 |
| BOS | Hyannis | December 8 to December 15 | $549 |
| EWR | Provincetown | November 6 to November 7 | $605 |
| JFK | Nantucket | January 4 to January 26 | $669 |
| JFK | Hyannis | December 17 to December 28 | $720 |
| DCA | Provincetown | November 6 to November 8 | $932 |
| ORD | Nantucket | December 4 to December 6 | $1,030 |
| ORD | Hyannis | November 5 to November 9 | $1,084 |
| DCA | Hyannis | November 25 to November 29 | $1,095 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| BOS | Provincetown | October 30 to November 8 | $330 |
| BWI | Boston | November 1 to November 7 | $350 |
| ORD | Boston | November 1 to November 4 | $368 |
| LGA | Boston | November 1 to November 2 | $447 |
| BOS | Hyannis | October 31 to November 6 | $460 |
| BOS | Nantucket | November 1 to November 3 | $553 |
| SAT | Boston | October 31 to November 3 | $709 |
| JFK | Nantucket | November 1 to November 8 | $736 |
| LIN | Boston | November 1 to November 18 | $777 |
| JFK | Hyannis | November 1 to November 6 | $838 |
| FCO | Boston | November 1 to November 14 | $867 |
| FCO | Boston | November 1 to November 14 | $867 |
| DCA | Nantucket | October 30 to November 6 | $1,093 |
Chatham Flight Information
Traveling to | Chatham |
|---|---|
Lowest Price | $117 |
Number of Airlines Serving | |
Airlines Serving | Delta, American Airlines |
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
$387 nightly
The price is $443 total per night from Nov 2 to Nov 3
$443 total
Nov 2 - Nov 3
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! (873 reviews)
"Amazing property and staff."
Reviewed on Oct 18, 2026
The Chatham Motel
1487 Main Street Chatham MA
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! (642 reviews)
"Room was comfortable,clean and very accessible. Polite staff. The stairs and wood walk porch in front of building are in need of some repair with nails sticking out. Tricky walking when wet. Off season so no pool open as it’s outdoors."
Reviewed on Oct 17, 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
$387 nightly
The price is $443 total per night from Nov 2 to Nov 3
$443 total
Nov 2 - Nov 3
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! (873 reviews)
"Amazing property and staff."
Reviewed on Oct 18, 2026
The Chatham Motel
1487 Main Street Chatham MA
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! (642 reviews)
"Room was comfortable,clean and very accessible. Polite staff. The stairs and wood walk porch in front of building are in need of some repair with nails sticking out. Tricky walking when wet. Off season so no pool open as it’s outdoors."
Reviewed on Oct 17, 2026
Greyfinch Chatham Inn
946 Main Street (Rte 28) Chatham MA
$203 nightly
The price is $233 total per night from Nov 1 to Nov 2
$233 total
Nov 1 - Nov 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! (298 reviews)
"Good location, Overpriced in my opinion. Was clean. For the price I would shop around more."
Reviewed on Oct 26, 2026
Save an average of 15% on thousands of hotels when you're signed in
Old Harbor Inn
22 Old Harbor Rd. Chatham MA
$395 nightly
The price is $452 total per night from Nov 1 to Nov 2
$452 total
Nov 1 - Nov 2
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! (173 reviews)
"We thoroughly enjoyed or 25th anniversary weekend at the Old Harbor inn! The staff and owner’s were amazing. The inn was well maintained the atmosphere and amenities were on point. The room was super and clean. The breakfast was great. Thanks to all who made our stay very enjoyable! We will be recommending ..."
Reviewed on Oct 12, 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
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! (642 reviews)
"Room was comfortable,clean and very accessible. Polite staff. The stairs and wood walk porch in front of building are in need of some repair with nails sticking out. Tricky walking when wet. Off season so no pool open as it’s outdoors."
Reviewed on Oct 17, 2026
Chatham Bars Inn
297 Shore Rd Chatham MA
$387 nightly
The price is $443 total per night from Nov 2 to Nov 3
$443 total
Nov 2 - Nov 3
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! (873 reviews)
"Amazing property and staff."
Reviewed on Oct 18, 2026
Pleasant Bay Village Resort
1191 Orleans Road Chatham MA
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 ...
Save an average of 15% on thousands of hotels when you're signed in
Greyfinch Chatham Inn
946 Main Street (Rte 28) Chatham MA
$203 nightly
The price is $233 total per night from Nov 1 to Nov 2
$233 total
Nov 1 - Nov 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! (298 reviews)
Families like: Outdoor pool, close to beach, bicycle rentals
Travelers say...
"Good location, Overpriced in my opinion. Was clean. For the price I would shop around more."
Reviewed on Oct 26, 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 - business class flights
Price found within the past 48 hours. Click for updated prices.
Need a Car For After Your Flight?
Economy Special
Boston, Massachusetts, USA
$34
$118 total
found 2 days ago
Standard SUV
Boston, Massachusetts, USA
$36
$123 total
found 2 days ago
Midsize Special
Boston, Massachusetts, USA
$36
$124 total
found 2 days ago
Compact
Boston, Massachusetts, USA
$38
$128 total
found 2 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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