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Chatham

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Chatham Flights as Low as $119

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

United
Thu, Sep 4 - Thu, Sep 4
ORD
O'Hare Intl.
BOS
Logan Intl.
$119 Roundtrip, found 15 hours ago
$119
Roundtrip
found 15 hours ago
Select United flight, departing Thu, Sep 4 from O'Hare Intl. to Logan Intl., returning Thu, Sep 4, priced at $119 found 15 hours ago
Spirit Airlines
Wed, Aug 20 - Sat, Sep 6
ORD
O'Hare Intl.
BOS
Logan Intl.
$126 Roundtrip, found 6 days ago
$126
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Aug 20 from O'Hare Intl. to Logan Intl., returning Sat, Sep 6, priced at $126 found 6 days ago
JetBlue Airways
Thu, Sep 4 - Mon, Sep 8
ORD
O'Hare Intl.
BOS
Logan Intl.
$129 Roundtrip, found 12 hours ago
$129
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Thu, Sep 4 from O'Hare Intl. to Logan Intl., returning Mon, Sep 8, priced at $129 found 12 hours ago
American Airlines
Thu, Sep 4 - Mon, Sep 8
ORD
O'Hare Intl.
BOS
Logan Intl.
$129 Roundtrip, found 12 hours ago
$129
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Logan Intl., returning Mon, Sep 8, priced at $129 found 12 hours ago
JetBlue Airways
Wed, Sep 3 - Wed, Sep 3
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$134 Roundtrip, found 11 hours ago
$134
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Wed, Sep 3 from Ronald Reagan Washington National to Logan Intl., returning Wed, Sep 3, priced at $134 found 11 hours ago
JetBlue Airways
Fri, Sep 5 - Sat, Sep 6
ORD
O'Hare Intl.
BOS
Logan Intl.
$137 Roundtrip, found 22 hours ago
$137
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Fri, Sep 5 from O'Hare Intl. to Logan Intl., returning Sat, Sep 6, priced at $137 found 22 hours ago
JetBlue Airways
Fri, Aug 8 - Wed, Aug 13
ORD
O'Hare Intl.
BOS
Logan Intl.
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, Aug 8 from O'Hare Intl. to Logan Intl., returning Wed, Aug 13, priced at $139 found 1 day ago
Delta
Mon, Aug 11 - Wed, Aug 13
ORD
O'Hare Intl.
BOS
Logan Intl.
$139 Roundtrip, found 6 hours ago
$139
Roundtrip
found 6 hours ago
Select Delta flight, departing Mon, Aug 11 from O'Hare Intl. to Logan Intl., returning Wed, Aug 13, priced at $139 found 6 hours ago
JetBlue Airways
Tue, Aug 12 - Thu, Aug 21
ORD
O'Hare Intl.
BOS
Logan Intl.
$140 Roundtrip, found 3 days ago
$140
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Aug 12 from O'Hare Intl. to Logan Intl., returning Thu, Aug 21, priced at $140 found 3 days ago
Delta
Sat, Oct 11 - Sat, Oct 18
ORD
O'Hare Intl.
BOS
Logan Intl.
$142 Roundtrip, found 22 hours ago
$142
Roundtrip
found 22 hours ago
Select Delta flight, departing Sat, Oct 11 from O'Hare Intl. to Logan Intl., returning Sat, Oct 18, priced at $142 found 22 hours ago
Spirit Airlines
Wed, Sep 10 - Mon, Sep 15
ORD
O'Hare Intl.
BOS
Logan Intl.
$154 Roundtrip, found 7 hours ago
$154
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Wed, Sep 10 from O'Hare Intl. to Logan Intl., returning Mon, Sep 15, priced at $154 found 7 hours ago
Spirit Airlines
Tue, Sep 2 - Sat, Sep 6
LAX
Los Angeles Intl.
BOS
Logan Intl.
$172 Roundtrip, found 8 hours ago
$172
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Tue, Sep 2 from Los Angeles Intl. to Logan Intl., returning Sat, Sep 6, priced at $172 found 8 hours ago
Frontier Airlines
Fri, Sep 5 - Sat, Sep 6
ORD
O'Hare Intl.
BOS
Logan Intl.
$218 Roundtrip, found 22 hours ago
$218
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Fri, Sep 5 from O'Hare Intl. to Logan Intl., returning Sat, Sep 6, priced at $218 found 22 hours ago
Alaska Airlines
Fri, Oct 31 - Mon, Nov 3
LAX
Los Angeles Intl.
BOS
Logan Intl.
$270 Roundtrip, found 5 hours ago
$270
Roundtrip
found 5 hours ago
Select Alaska Airlines flight, departing Fri, Oct 31 from Los Angeles Intl. to Logan Intl., returning Mon, Nov 3, priced at $270 found 5 hours ago
JetBlue Airways
Mon, Sep 8 - Fri, Sep 12
DCA
Ronald Reagan Washington National
HYA
Barnstable Municipal
$361 Roundtrip, found 12 hours ago
$361
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Mon, Sep 8 from Ronald Reagan Washington National to Barnstable Municipal, returning Fri, Sep 12, priced at $361 found 12 hours ago
JetBlue Airways
Mon, Sep 8 - Thu, Sep 18
DCA
Ronald Reagan Washington National
PVC
Provincetown Municipal
$402 Roundtrip, found 11 hours ago
$402
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Mon, Sep 8 from Ronald Reagan Washington National to Provincetown Municipal, returning Thu, Sep 18, priced at $402 found 11 hours 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 September, 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 $119, 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 $119 right now, why wait?

Chatham Flight Information
Destination airport
Portsmouth Intl.
Destination airport IATA code
PSM
Roundtrip price
$101

Last Minute Hotel Deals in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
Stay at this 5-star 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! (775 reviews)
"Old school hotel complex in a great location overlooking the Sea. Great ambience in the main lodge & dining facilities. Very kid friendly with the main pool swarming with kids. At one point I noticed 8 small kids in the large jacuzzi at one time - unusual for a luxury property. The pool experience ..."

Reviewed on Jul 16, 2025

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Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St, Chatham, MA
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! (532 reviews)
"We had a wonderful time. The property is centrally located, and we walked most everywhere."

Reviewed on Aug 1, 2025

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Chatham Wayside Inn
The Chatham Motel

The Chatham Motel

2 out of 5
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! (614 reviews)
"Room was spacious and clean."

Reviewed on Jul 10, 2025

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The Chatham Motel
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! (184 reviews)
"I stayed there for a wedding. The staff was super helpful and really went above and beyond. The place was beautifully kept and had a charming vibe. I’d definitely recommend it!"

Reviewed on Jul 18, 2025

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The Hawthorne
Hyannis Plaza Hotel

Hyannis Plaza Hotel

2.5 out of 5
662 Main Street, Hyannis, MA
Book a stay at this luxury hotel in Hyannis. Enjoy free parking, an outdoor pool, and a 24-hour front desk. Popular attractions Hyannis Harbor and Cape Codder ...
6.8/10 (815 reviews)
"Parking was not an issue. Room's were spacious and clean and beds comfortable. There was minimal towels in bathroom and the TV kept freezing up for a second or two at times. The pool towels, when available were very small. The handle on the pool stairs was very wobbly, and pool needs renovating. ..."

Reviewed on Jul 31, 2025

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Hyannis Plaza Hotel
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28, West Yarmouth, MA
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. ...
8.6/10 Excellent! (1,444 reviews)
"Jon at Moby Dick Pub was an absolute legend."

Reviewed on Aug 1, 2025

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Bayside Resort Hotel
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd, Hyannis, MA
Stay at this 4-star 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 ...
8.6/10 Excellent! (236 reviews)
"clean, smart and safe."

Reviewed on Jul 28, 2025

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Margaritaville Resort Cape Cod
Cape Sands Inn

Cape Sands Inn

2.5 out of 5
149 Main St - RT 28, West Yarmouth, MA
Book a stay at this family-friendly motel in West Yarmouth. Enjoy free parking, an outdoor pool, and a sauna. Our guests praise the pool and the helpful staff ...
8.2/10 Very Good! (1,008 reviews)
"Needed a little updating (painting, minor repairs). Was a little bit damp but easily fixed with a dehumidifier. Beds, internet and location were all positive. The staff and their customer service skills were impeccable. Would most definitely stay again."

Reviewed on Aug 1, 2025

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Cape Sands Inn
See all 5,033 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.