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It's time to fly. What's waiting for you in Chatham?

Perhaps you’re searching cheap flights to Chatham for a much-needed vacation or you simply have to roll in to see the relatives. Either way, we say rock that family reunion. Tell one too many stories at the hotel bar. Traveling for work? Crush it. If you lie back and relax without your cell phone, we won’t tell.

In the end you want to score a great deal and have a fantastic time, right? Flying is a small part of the whole adventure. We get that. Wherever you’re excited to go – or get away from – start this story with Hotwire’s cheap flights to Chatham.

Not sure how to get the best price on plane tickets to Chatham?

We know there are some airline aficionados out there. If you don’t know the industry like the back of your hand, don’t worry. You can make spending less look good with our booking tips.

Search certain days of the week for Chatham flights

For better savings, consider departing on a Wednesday, Thursday or Saturday. Return on a Sunday, Tuesday or Wednesday. International deals are often available when departing Monday through Thursday.

Change up your days for cheaper weekend getaways

Jetting off on Thursday and returning on Sunday is generally less expensive than flying on Friday and returning on Monday.

Stay a Saturday night to play more

Spending the weekend at your destination will generally result in lower airfares. We’re all for that.

Consider alternate airports when searching Chatham flights

Other nearby airports may offer different fares from your current search results. Clicking “Nearby Airports” after your initial search will give a list of the closest options.

See a fare that you like? Pounce!

Coordinate with your travel buddies before searching and you’ll be able to act quickly when it’s time to book. Airline ticket prices often change in minutes. We know you’re combing for the best prices but so is everyone else! If the deal is right, snag it and feel the sweet satisfaction of booking victory.

Fly during the off-peak season

Certain travel destinations have especially high volume during particular seasons. For example, Europe, Hawaii and Alaska are big hits in the summer. Florida, New Orleans and Southern California are the most popular in springtime. Winter is prime for Mexico and the Caribbean, as well as ski and snowboard destinations like the Colorado Rockies. In the autumn, Northern California, the Pacific Northwest and New England draw visitors. Flying during less popular periods can mean extra money in your wallet – yes, please!

Last Minute Hotel Deals in Chatham

See all 296 Properties in Chatham
Berkshire Plaza Hotel

Berkshire Plaza Hotel

1 West St, Pittsfield
    3.5 out of 5.0
     
     

    Located in the heart of Pittsfield, this spa hotel is within a 5-minute walk of Berkshire Museum, Colonial Theater, and Berkshire Athenaeum. Canoe Meadows Wildlife ...

    Berkshire Plaza Hotel$84

    Berkshire Plaza Hotel$84
    The Wick, Hudson, A Tribute Portfolio Hotel

    The Wick, Hudson, A Tribute Portfolio Hotel

    41 Cross Street, Hudson
      4.0 out of 5.0
       
       

      Situated in Hudson, this boutique hotel is within a 10-minute walk of Max and Lillian Katzman Theater and Hudson Opera House. Hudson Area Library and FASNY Museum ...

      The Wick, Hudson, A Tribute Portfolio Hotel$84

      The Wick, Hudson, A Tribute Portfolio Hotel$84
      Vacation Village in the Berkshires

      Vacation Village in the Berkshires

      276 Brodie Mountain Rd, Hancock
        3.0 out of 5.0
         
         

        Situated in Hancock, this condo building is within 9 mi (15 km) of Mount Greylock State Reservation Visitor Center, Pittsfield State Forest, and Waubeeka Golf ...

        Vacation Village in the Berkshires$151

        Vacation Village in the Berkshires$151
        Hilton Garden Inn Lenox Pittsfield

        Hilton Garden Inn Lenox Pittsfield

        1032 South Street, Pittsfield
          3.0 out of 5.0
           
           

          Situated in Pittsfield, this hotel is 1.2 mi (1.9 km) from Bousquet Ski Area and within 3 mi (5 km) of Arrowhead Museum and Colonial Theater. Berkshire Museum ...

          Hilton Garden Inn Lenox Pittsfield$111

          Hilton Garden Inn Lenox Pittsfield$111