Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Chesterton Vacations

Pack those stellar shades. We have Chesterton vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Chesterton – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Chesterton vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Chesterton

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Chesterton vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Chesterton well.

Chesterton Flight + Hotel packages

Top Hotel Deals

See all 157 Hotels in Chesterton
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

501 Gateway Boulevard, Chesterton
    3.0 out of 5.0
     
     

    Situated in Chesterton, this hotel is 5.5 mi (8.9 km) from Indiana Dunes National Lakeshore and within 12 mi (20 km) of Indiana Dunes State Park and Valparaiso ...

    Hilton Garden Inn Chesterton$99

    Hilton Garden Inn Chesterton$99
    Waterbird Lakeside Inn

    Waterbird Lakeside Inn

    556 Indian Boundary Road, Chesterton
      2.0 out of 5.0
       
       

      Situated on a lake, this hotel is 2.8 mi (4.5 km) from Indiana Dunes National Lakeshore and within 12 mi (20 km) of Indiana Dunes State Park and Lighthouse Place ...

      Quality Inn

      Quality Inn

      418 Council Road, Chesterton
        2.5 out of 5.0
         
         

        Located in the heart of Chesterton, this hotel is 2.9 mi (4.7 km) from Indiana Dunes National Lakeshore and 4.2 mi (6.7 km) from Indiana Dunes State Park. Lighthouse ...

        Quality Inn$70

        Quality Inn$70
        Econo Lodge Chesterton

        Econo Lodge Chesterton

        713 Plaza Dr., Chesterton
          1.5 out of 5.0
           
           

          Located in the heart of Chesterton, this hotel is 2.8 mi (4.5 km) from Indiana Dunes National Lakeshore and 4.1 mi (6.5 km) from Indiana Dunes State Park. Lighthouse ...

          Econo Lodge Chesterton$51

          Econo Lodge Chesterton$51
          Best Western Indian Oak

          Best Western Indian Oak

          558 Indian Boundary Road, Chesterton
            2.5 out of 5.0
             
             

            Situated near the beach, this hotel is 2.8 mi (4.5 km) from Indiana Dunes National Lakeshore and within 12 mi (20 km) of Indiana Dunes State Park and Lighthouse ...

            Best Western Indian Oak$76

            Best Western Indian Oak$76
            Riley's Railhouse

            Riley's Railhouse

            123 N 4th St, Chesterton
              3.0 out of 5.0
               
               
              Blue Chip Casino Hotel and Spa

              Blue Chip Casino Hotel and Spa

              777 Blue Chip Drive, Michigan City
                3.5 out of 5.0
                 
                 

                Situated in Michigan City, this spa hotel is within 1 mi (2 km) of Washington Park Zoo and Lighthouse Place Premium Outlets. Whittaker Woods Golf Course and ...

                Blue Chip Casino Hotel and Spa$80

                Blue Chip Casino Hotel and Spa$80
                Red Roof Inn Merrillville

                Red Roof Inn Merrillville

                8290 Georgia St, Merrillville
                  2.0 out of 5.0
                   
                   

                  Situated in Merrillville, this motel is 0.8 mi (1.3 km) from Star Plaza Theatre and within 9 mi (15 km) of Deep River Water Park and Indiana University Northwest. ...

                  Red Roof Inn Merrillville$52

                  Red Roof Inn Merrillville$52
                  Baymont by Wyndham Michigan City

                  Baymont by Wyndham Michigan City

                  4128 South Franklin Street, Michigan City
                     
                     

                    Located in the heart of Michigan City, this hotel is 2.6 mi (4.2 km) from Lighthouse Place Premium Outlets and within 9 mi (15 km) of Washington Park Zoo and ...

                    Baymont by Wyndham Michigan City$65

                    Baymont by Wyndham Michigan City$65
                    Baymont by Wyndham New Buffalo

                    Baymont by Wyndham New Buffalo

                    18800 Harbor Country Drive, New Buffalo
                      2.5 out of 5.0
                       
                       

                      Situated in New Buffalo, this hotel is 1.3 mi (2.1 km) from New Buffalo Public Beach and 2.2 mi (3.5 km) from Whittaker Woods Golf Course. Legacy Hills Golf ...

                      Baymont by Wyndham New Buffalo$70

                      Baymont by Wyndham New Buffalo$70

                      Top Flight Deals

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