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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 , 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  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 , 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  right now, why wait?

Chatham Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$187

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 ...
9/10 Wonderful! (802 reviews)
Room was very clean but a little dated also there is very little space to put your clothes away…no dressers

Reviewed on Jan 3, 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! (614 reviews)
I’ve always been curious about the Wayside Inn because my mom worked there a gazillion years ago when she was in high school. It’s so cozy and clean and staff was very friendly. They also upgraded us which was super nice! The only thing was outlets in the room were kind of oddly positioned— but we ...

Reviewed on Jan 4, 2026

Chatham Wayside Inn
Surfside Inn Chatham

Surfside Inn Chatham

2.5 out of 5
25 Holway St Chatham MA
Book a stay at this beach B&B in Chatham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chatham Lighthouse and Chatham Windmill are ...
8/10 Very Good! (159 reviews)
This is a beautiful property very centrally located. I highly recommend the surfside inn.

Reviewed on Oct 15, 2025

Surfside Inn Chatham
The Hawthorne

The Hawthorne

2 out of 5
196 Shore Rd Chatham MA
Book a stay at this beach hotel in Chatham. Enjoy free WiFi, free parking, and a private beach. Popular attractions Chatham Seaside Links and Mayo House are ...
9.2/10 Wonderful! (195 reviews)
This is the find!! Water front efficiency units-- while they may be small, they do the job. You can not find anything else like them. And the owners are wonderful. I understand now why so many people return here annually.

Reviewed on Nov 15, 2025

The Hawthorne
Captain's House Inn

Captain's House Inn

4 out of 5
369 Old Harbor Road Chatham MA
Stay at this 4-star B&B in Chatham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chatham Fish Pier and Chatham Shark Center are located ...
9.6/10 Exceptional! (215 reviews)
Great place to stay in Chatham. Went for First Night celebrations and the Inn was clean and comfortable and served one of the best breakfasts! Highly recommend!

Reviewed on Jan 3, 2026

Captain's House Inn
Queen Anne Inn

Queen Anne Inn

4 out of 5
70 Queen Anne Rd Chatham MA
Book a stay at this business-friendly hotel in Chatham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (238 reviews)
Great breakfast, nice pool area

Reviewed on Nov 7, 2025

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! (304 reviews)
Fantastic hotel! Super friendly, helpful staff, clean and spacious rooms, beautiful propert!

Reviewed on Nov 2, 2025

Pleasant Bay Village Resort
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
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! (668 reviews)
The hotel is being remodeled, but the room is very clean. They even had gluten free options for breakfast, which made my little one super happy!

Reviewed on Jan 3, 2026

Fairfield Inn & Suites by Marriott Cape Cod Hyannis
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.