Cheap Flights to Chatham from $72
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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 $147 and $72 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
ACK
Nantucket Memorial
$167 Roundtrip, found 3 hours ago
$167
Roundtrip
found 3 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| JFK | Boston | July 18 to July 18 | $147 |
| ORD | Nantucket | July 11 to July 15 | $162 |
| ORD | Hyannis | August 11 to August 15 | $167 |
| JFK | Hyannis | July 22 to July 22 | $195 |
| JFK | Nantucket | August 12 to August 12 | $201 |
| BOS | Nantucket | September 10 to September 12 | $227 |
| SAT | Boston | September 5 to September 10 | $239 |
| BOS | Provincetown | June 21 to June 25 | $245 |
| BOS | Hyannis | June 27 to July 1 | $269 |
| EWR | Provincetown | June 21 to June 30 | $518 |
| FCO | Boston | September 5 to October 4 | $536 |
| FCO | Boston | September 5 to October 4 | $536 |
| MXP | Boston | August 27 to September 14 | $559 |
| ORD | Provincetown | June 28 to July 3 | $595 |
| SAT | Provincetown | July 2 to July 5 | $1,330 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| BOS | Provincetown | June 14 to June 19 | $236 |
| BOS | Hyannis | June 14 to June 17 | $307 |
| JFK | Boston | June 14 to July 5 | $316 |
| ORD | Boston | June 13 to June 14 | $324 |
| DCA | Nantucket | June 13 to June 15 | $364 |
| LGA | Nantucket | June 13 to June 15 | $384 |
| BOS | Nantucket | June 14 to June 18 | $397 |
| DCA | Boston | June 13 to June 15 | $399 |
| ORD | Nantucket | June 13 to June 17 | $487 |
| JFK | Hyannis | June 13 to June 16 | $554 |
| SAT | Boston | June 13 to June 18 | $611 |
| FCO | Boston | June 14 to June 30 | $690 |
| FCO | Boston | June 14 to June 30 | $690 |
| MXP | Boston | June 13 to June 17 | $740 |
| EWR | Provincetown | June 13 to June 15 | $1,348 |
Chatham Flight Information
Traveling to | Chatham |
|---|---|
Lowest Price | $147 |
Number of Airlines Serving | |
Airlines Serving | 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
$1,025 nightly
The price is $1,173 total per night from Jun 23 to Jun 24
$1,173 total
Jun 23 - Jun 24
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! (835 reviews)
"Lovely hotel. We had a cottage which had lovely views out across the sandbars. Only downside was the weather but that wasn’t an issue in such lovely surroundings."
Reviewed on Jun 5, 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 Hardings Beach and Ridgevale Beach are located ...
9.2/10 Wonderful! (631 reviews)
"Very safe . Cafe Mood great food run by Jamaican family"
Reviewed on Oct 11, 2025
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
$1,025 nightly
The price is $1,173 total per night from Jun 23 to Jun 24
$1,173 total
Jun 23 - Jun 24
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! (835 reviews)
"Lovely hotel. We had a cottage which had lovely views out across the sandbars. Only downside was the weather but that wasn’t an issue in such lovely surroundings."
Reviewed on Jun 5, 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 Hardings Beach and Ridgevale Beach are located ...
9.2/10 Wonderful! (631 reviews)
"Very safe . Cafe Mood great food run by Jamaican family"
Reviewed on Oct 11, 2025
Greyfinch Chatham Inn
946 Main Street (Rte 28) Chatham MA
$371 nightly
The price is $425 total per night from Jun 14 to Jun 15
$425 total
Jun 14 - Jun 15
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! (265 reviews)
"Lovely room and central location, but our room had humidity issues that decreased our satisfaction with our stay."
Reviewed on Jun 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
$419 nightly
The price is $480 total per night from Jun 14 to Jun 15
$480 total
Jun 14 - Jun 15
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 Gallery Antonia are located ...
9.6/10 Exceptional! (163 reviews)
"This is not a hotel, which, since I booked via Hotels.com, I expected that it would be. Apparently, in New England an Inn is not a hotel. Holiday Inn is a hotel and they have Inn in the name, so we don’t know. It’s basically a $700 a night bed and breakfast. Clean and appears new, nicely appointed, ..."
Reviewed on May 30, 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 Hardings Beach and Ridgevale Beach are located ...
9.2/10 Wonderful! (631 reviews)
"Very safe . Cafe Mood great food run by Jamaican family"
Reviewed on Oct 11, 2025
Chatham Bars Inn
297 Shore Rd Chatham MA
$1,025 nightly
The price is $1,173 total per night from Jun 23 to Jun 24
$1,173 total
Jun 23 - Jun 24
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! (835 reviews)
"Lovely hotel. We had a cottage which had lovely views out across the sandbars. Only downside was the weather but that wasn’t an issue in such lovely surroundings."
Reviewed on Jun 5, 2026
Pleasant Bay Village Resort
1191 Orleans Road Chatham MA
$254 nightly
The price is $290 total per night from Jun 15 to Jun 16
$290 total
Jun 15 - Jun 16
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! (307 reviews)
"This place was gorgeous and the staff was so kind and helpful. They gave me so many good recommendations and went above and beyond to make my stay memorable. Highly recommend!"
Reviewed on Jun 5, 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
$371 nightly
The price is $425 total per night from Jun 14 to Jun 15
$425 total
Jun 14 - Jun 15
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! (265 reviews)
Families like: Outdoor pool, close to beach, bicycle rentals
Travelers say...
"Lovely room and central location, but our room had humidity issues that decreased our satisfaction with our stay."
Reviewed on Jun 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 - first class flights
Price found within the past 48 hours. Click for updated prices.
Need a Car For After Your Flight?
Special
East Boston, Massachusetts, USA
$57
$176 total
found 2 days ago
Economy
East Boston, Massachusetts, USA
$58
$179 total
found 3 days ago
Compact
East Boston, Massachusetts, USA
$59
$183 total
found 3 days ago
Midsize
East Boston, Massachusetts, USA
$62
$189 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
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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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