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Chatham

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Chatham Flights as Low as $246

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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 August, 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 15 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 $246, 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 $246 right now, why wait?

Chatham Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$114

Last Minute Hotel Deals in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
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! (841 reviews)
"Great experience"

Reviewed on Jun 21, 2026

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
Book a stay at this 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! (697 reviews)
"Great pool and location"

Reviewed on Jun 22, 2026

Chatham Wayside Inn
Queen Anne Inn

Queen Anne Inn

4 out of 5
70 Queen Anne Rd Chatham MA
Stay at this hotel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Harwich ...
8.8/10 Excellent! (240 reviews)
"I was so happy with this hotel!! When I got to my room, I couldn’t find the TV remote - the woman at the desk came to help me find it and noticed that the fridge in the room was making a strange sound. She knew I needed the fridge to store insulin, so just to be safe she moved me to a different room, ..."

Reviewed on Jun 22, 2026

Queen Anne Inn
Pleasant Bay Village Resort

Pleasant Bay Village Resort

3 out of 5
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 ...
9.6/10 Exceptional! (316 reviews)
"Such a wonderful surprise. This hotel has been in business for over 50 years in the same family. How did we not know about this place sooner?! Everything was clean; pool and hot tub were large. Staff was super friendly and nice. The grounds...oh my! They have poured an incredible amount of time and ..."

Reviewed on Jun 24, 2026

Pleasant Bay Village Resort
Greyfinch Chatham Inn

Greyfinch Chatham Inn

3 out of 5
946 Main Street (Rte 28) Chatham MA
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! (268 reviews)
"We had a great stay at the Greyfinch Inn … just too short! Staff at reception were cheerful, welcoming and gave us good dining recommendations. Room was clean, bright and cozy. Bed was super comfy! Located in great proximity to both the center of Chatham and to nearby beaches. Can’t wait to return ..."

Reviewed on Jun 15, 2026

Greyfinch Chatham Inn
Chatham Seafarer Inn

Chatham Seafarer Inn

3.5 out of 5
2079 Main St Chatham MA
Stay at this hotel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ocean Edge Golf Club and Cockle Cove Beach are located ...
9/10 Wonderful! (325 reviews)
"The room was very clean. Shower was easy to use. Very nice pool area in a quiet atmosphere. Would go there again."

Reviewed on Jun 23, 2026

Chatham Seafarer Inn
Riviera Beach Resort

Riviera Beach Resort

3 out of 5
327 South Shore Drive South Yarmouth MA
Book a stay at this beach hotel in South Yarmouth. Enjoy free WiFi, an outdoor pool, and a private beach. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (1,005 reviews)
"Staff was friendly & helpful."

Reviewed on Jun 27, 2026

Riviera Beach Resort
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd Hyannis MA
Book a stay at this spa resort in Hyannis. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the clean rooms in our reviews. Popular attractions ...
8.8/10 Excellent! (602 reviews)
"Very nice property. Room was very good. Had all the amenities you need for a good comfortable stay. I would stay there again."

Reviewed on Jun 25, 2026

Margaritaville Resort Cape Cod
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.