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Chatham

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Chatham Flights as Low as $56

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Tue, May 6 - Tue, May 13
MCO
Orlando Intl.
BOS
Logan Intl.
$56 Roundtrip, found 3 days ago
$56
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, May 6 from Orlando Intl. to Logan Intl., returning Tue, May 13, priced at $56 found 3 days ago
Spirit Airlines
Tue, Jun 3 - Wed, Jun 4
MCO
Orlando Intl.
BOS
Logan Intl.
$60 Roundtrip, found 3 days ago
$60
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Jun 3 from Orlando Intl. to Logan Intl., returning Wed, Jun 4, priced at $60 found 3 days ago
Frontier Airlines
Tue, May 6 - Tue, May 13
MCO
Orlando Intl.
BOS
Logan Intl.
$61 Roundtrip, found 3 days ago
$61
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, May 6 from Orlando Intl. to Logan Intl., returning Tue, May 13, priced at $61 found 3 days ago
Spirit Airlines
Tue, May 6 - Tue, May 13
MCO
Orlando Intl.
BOS
Logan Intl.
$62 Roundtrip, found 3 days ago
$62
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, May 6 from Orlando Intl. to Logan Intl., returning Tue, May 13, priced at $62 found 3 days ago
Spirit Airlines
Tue, May 6 - Tue, May 13
MCO
Orlando Intl.
BOS
Logan Intl.
$63 Roundtrip, found 3 days ago
$63
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, May 6 from Orlando Intl. to Logan Intl., returning Tue, May 13, priced at $63 found 3 days ago
Spirit Airlines
Tue, May 6 - Tue, May 13
MCO
Orlando Intl.
BOS
Logan Intl.
$67 Roundtrip, found 3 days ago
$67
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, May 6 from Orlando Intl. to Logan Intl., returning Tue, May 13, priced at $67 found 3 days ago
Spirit Airlines
Tue, May 6 - Tue, May 13
MCO
Orlando Intl.
BOS
Logan Intl.
$68 Roundtrip, found 3 days ago
$68
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, May 6 from Orlando Intl. to Logan Intl., returning Tue, May 13, priced at $68 found 3 days ago
Frontier Airlines
Tue, May 20 - Thu, May 22
MCO
Orlando Intl.
BOS
Logan Intl.
$73 Roundtrip, found 4 days ago
$73
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, May 20 from Orlando Intl. to Logan Intl., returning Thu, May 22, priced at $73 found 4 days ago
Frontier Airlines
Mon, Jun 9 - Wed, Jun 11
MCO
Orlando Intl.
BOS
Logan Intl.
$76 Roundtrip, found 1 day ago
$76
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Jun 9 from Orlando Intl. to Logan Intl., returning Wed, Jun 11, priced at $76 found 1 day ago
Spirit Airlines
Tue, May 6 - Tue, May 13
MCO
Orlando Intl.
BOS
Logan Intl.
$77 Roundtrip, found 3 days ago
$77
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, May 6 from Orlando Intl. to Logan Intl., returning Tue, May 13, priced at $77 found 3 days ago
Breeze Airways
Wed, Jun 4 - Sat, Jun 7
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 10 hours ago
$102
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Wed, Jun 4 from Orlando Intl. to Portsmouth Intl., returning Sat, Jun 7, priced at $102 found 10 hours ago
JetBlue Airways
Fri, Mar 21 - Mon, Mar 31
MCO
Orlando Intl.
BOS
Logan Intl.
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, Mar 21 from Orlando Intl. to Logan Intl., returning Mon, Mar 31, priced at $157 found 2 days ago
Delta
Sat, Mar 22 - Sun, Mar 30
MCO
Orlando Intl.
BOS
Logan Intl.
$189 Roundtrip, found 2 days ago
$189
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Mar 22 from Orlando Intl. to Logan Intl., returning Sun, Mar 30, priced at $189 found 2 days ago
United
Thu, Jun 5 - Mon, Jun 9
MCO
Orlando Intl.
BOS
Logan Intl.
$207 Roundtrip, found 3 days ago
$207
Roundtrip
found 3 days ago
Select United flight, departing Thu, Jun 5 from Orlando Intl. to Logan Intl., returning Mon, Jun 9, priced at $207 found 3 days ago
American Airlines
Wed, Jun 4 - Sat, Jun 7
MCO
Orlando Intl.
BOS
Logan Intl.
$247 Roundtrip, found 10 hours ago
$247
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Wed, Jun 4 from Orlando Intl. to Logan Intl., returning Sat, Jun 7, priced at $247 found 10 hours ago
Delta
Tue, Mar 25 - Tue, Apr 1
MCO
Orlando Intl.
HYA
Barnstable Municipal
$572 Roundtrip, found 2 days ago
$572
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Mar 25 from Orlando Intl. to Barnstable Municipal, returning Tue, Apr 1, priced at $572 found 2 days ago

Cheap Flights to Chatham

Fall in love at first flight with your vacation to Chatham by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chatham on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chatham, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chatham

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chatham with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the PVC airport.

What is the cheapest month to fly to Chatham?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chatham are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chatham?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Chatham.

What airport is best to fly into Chatham?

When you’re planning your trip to Chatham, convenience is the name of the game. Luckily, Chatham Barnstable Municipal Airport is nearby so you can deplane and get going on checking off everything on your Chatham must-do list.

How much are flights to Chatham?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chatham on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $56, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chatham?

The trick to saving a stack of cash on your flight to Chatham? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $56 right now, why wait?

Chatham Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$82

Last Minute Hotel Deals in Chatham

Chatham Bars Inn
Chatham Bars Inn
5 out of 5
297 Shore Rd, Chatham, MA
The price is $312 per night from Mar 12 to Mar 13
$312
includes taxes & fees
Mar 12 - Mar 13
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 ...
9/10 Wonderful! (744 reviews)
"We loved our weekend getaway to the Chatham Bars Inn! What a beautiful place, and they keep it warm and cozy in the winter. The food, drinks, and fireplaces were all wonderful. Highly recommend!"

Reviewed on Feb 7, 2025

Chatham Bars Inn
Chatham Wayside Inn
Chatham Wayside Inn
4 out of 5
512 Main St, Chatham, MA
The price is $233 per night from Mar 13 to Mar 14
$233
includes taxes & fees
Mar 13 - Mar 14
Stay at this 4-star golf hotel in Chatham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
9.2/10 Wonderful! (469 reviews)
"Location within walking distance of town."

Reviewed on Feb 23, 2025

Chatham Wayside Inn
Margaritaville Resort Cape Cod
Margaritaville Resort Cape Cod
4 out of 5
1225 Iyannough Rd, Hyannis, MA
The price is $216 per night from Mar 11 to Mar 12
$216
includes taxes & fees
Mar 11 - Mar 12
Stay at this 4-star family-friendly resort in Hyannis. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the clean rooms in our reviews. Popular ...
8.2/10 Very Good! (99 reviews)
"We had a great time. The hotel is all renovate, the did an excellent job. Everything is clean, beautiful decored.. we loved it. My 3 year old daughter enjoyed so much, especially the water park. Food is great, staff is super friendly!! We will come back for sure."

Reviewed on Mar 7, 2025

Margaritaville Resort Cape Cod
Fairfield Inn & Suites by Marriott Cape Cod Hyannis
Fairfield Inn & Suites by Marriott Cape Cod Hyannis
2.5 out of 5
867 Iyannough Road, Hyannis, MA
The price is $117 per night from Mar 23 to Mar 24
$117
includes taxes & fees
Mar 23 - Mar 24
Book a stay at this business-friendly hotel in Hyannis. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (542 reviews)
"Will stay again!"

Reviewed on Feb 21, 2025

Fairfield Inn & Suites by Marriott Cape Cod Hyannis
Bayside Resort Hotel
Bayside Resort Hotel
3 out of 5
225 Route 28, West Yarmouth, MA
The price is $118 per night from Mar 11 to Mar 12
$118
includes taxes & fees
Mar 11 - Mar 12
Stay at this 3-star beach hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
8.8/10 Excellent! (1,290 reviews)
"This hotel is amazing!!!!! Room was completely clean and smells so good! Breakfast was incredible!!! We would stay here again for sure!"

Reviewed on Mar 5, 2025

Bayside Resort Hotel
Hampton Inn & Suites Cape Cod-West Yarmouth
Hampton Inn & Suites Cape Cod-West Yarmouth
2.5 out of 5
99 Main Street, Route 28, West Yarmouth, MA
The price is $107 per night from Mar 16 to Mar 17
$107
includes taxes & fees
Mar 16 - Mar 17
Book a stay at this family-friendly hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,000 reviews)
"Reliable"

Reviewed on Mar 7, 2025

Hampton Inn & Suites Cape Cod-West Yarmouth
Comfort Inn Hyannis - Cape Cod
Comfort Inn Hyannis - Cape Cod
2.5 out of 5
259 Main Street, Hyannis, MA
The price is $108 per night from Mar 16 to Mar 17
$108
includes taxes & fees
Mar 16 - Mar 17
Book a stay at this business-friendly hotel in Hyannis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7.6/10 Good! (1,012 reviews)
"What can I say? The Comfort Inn is a nice place to stay. The beds are comfortable."

Reviewed on Mar 8, 2025

Comfort Inn Hyannis - Cape Cod
Hyannis Travel Inn
Hyannis Travel Inn
2.5 out of 5
18 North St, Hyannis, MA
Stay at this hotel in Hyannis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
9.4/10 Exceptional! (1,000 reviews)
"Hyannis Travel Inn, MA This place was wonderful. The best thing about it was the staff. They will go out of their way to help you plan your stay. They have numerous recommendations across the entire Cape area for everything from food to shopping to activities. They know all about all the events going ..."

Reviewed on Jan 29, 2025

Get rates
Hyannis Travel Inn
See all 4,745 properties in Chatham
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.