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

Perhaps you’re searching cheap flights to Chesapeake Bay 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 Chesapeake Bay.

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

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 Chesapeake Bay 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 Chesapeake Bay 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 Chesapeake Bay

See all 2,989 Properties in Chesapeake Bay
Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

1001 14th St NW, Washington
    4.0 out of 5.0
     
     

    This hotel is 5 blocks from the White House and 8 blocks from the National Mall. The Washington Monument, National World War II Memorial, and Vietnam Veterans ...

    Hamilton Hotel Washington DC$98

    Hamilton Hotel Washington DC$98
    Grand Hyatt Washington

    Grand Hyatt Washington

    1000 H Street NW, Washington
      4.0 out of 5.0
       
       

      This Washington hotel sits just 4 blocks from the Capital One Arena, 6 blocks from the White House and just 7 blocks from the National Mall. The Smithsonian ...

      Grand Hyatt Washington$105

      Grand Hyatt Washington$105
      The Fairfax at Embassy Row, Washington, D.C.

      The Fairfax at Embassy Row, Washington, D.C.

      2100 Massachusetts Avenue NW, Washington
        4.0 out of 5.0
         
         

        This Washington, DC luxury hotel is in a shopping district, 2 blocks from Dupont Circle, 4 blocks from Georgetown, and 1 mile from the John F. Kennedy Center ...

        The Fairfax at Embassy Row, Washington, D.C.$119

        The Fairfax at Embassy Row, Washington, D.C.$119
        The Wink Hotel

        The Wink Hotel

        1143 New Hampshire Ave NW, Washington
          4.0 out of 5.0
           
           

          Located in Downtown Washington D.C., this hotel is within 1 mi (2 km) of George Washington University Hospital, White House, and Vietnam Veterans Memorial. Washington ...

          The Wink Hotel$89

          The Wink Hotel$89