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

Highland Vacations

Pack those stellar shades. We have Highland 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 Highland – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Highland 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 Highland

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 Highland 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 Highland well.

Highland Flight + Hotel packages

Top Hotel Deals

See all 142 Hotels in Highland
La Quinta Inn & Suites Chicago - Lake Shore

La Quinta Inn & Suites Chicago - Lake Shore

4900A S. Lake Shore Drive, Chicago
    3.0 out of 5.0
     
     

    Located in Kenwood, this hotel is 1.1 mi (1.7 km) from Chicago Museum of Science and Industry and 1.9 mi (3 km) from University of Chicago. Robie House and Jackson ...

    La Quinta Inn & Suites Chicago - Lake Shore$118

    La Quinta Inn & Suites Chicago - Lake Shore$118
    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
      La Quinta Inn & Suites Chicago Tinley Park

      La Quinta Inn & Suites Chicago Tinley Park

      7255 West 183rd St., Tinley Park
        2.5 out of 5.0
         
         

        Situated in the suburbs, this hotel is 0.5 mi (0.9 km) from Tinley Park Convention Center and 2.4 mi (3.8 km) from Hollywood Casino Amphitheatre. Coyote Run ...

        La Quinta Inn & Suites Chicago Tinley Park$79

        La Quinta Inn & Suites Chicago Tinley Park$79
        Sleep Inn Tinley Park

        Sleep Inn Tinley Park

        18420 Spring Creek Dr, Tinley Park
          2.5 out of 5.0
           
           

          Situated in Tinley Park, this hotel is 0.8 mi (1.2 km) from Tinley Park Convention Center and 2.6 mi (4.2 km) from Hollywood Casino Amphitheatre. Coyote Run ...

          Sleep Inn Tinley Park$79

          Sleep Inn Tinley Park$79
          Motel 6 Alsip

          Motel 6 Alsip

          5150 West 127th Street, Alsip
            2.0 out of 5.0
             
             

            Situated in Alsip, this motel is 2.3 mi (3.7 km) from Trinity Christian College and within 6 mi (10 km) of Gaelic Park and Childrens Museum of Oak Lawn. Chicago ...

            Motel 6 Alsip$49

            Motel 6 Alsip$49
            Ameristar Casino Hotel East Chicago

            Ameristar Casino Hotel East Chicago

            777 Ameristar Blvd., East Chicago
              4.0 out of 5.0
               
               

              Situated near the airport, this hotel is within a 15-minute walk of Ameristar Casino East Chicago and Indiana Harbor. Buffington Harbor and Lost Marsh Golf Course ...

              Ameristar Casino Hotel East Chicago$93

              Ameristar Casino Hotel East Chicago$93
              Best Western Plus Portage Hotel & Suites

              Best Western Plus Portage Hotel & Suites

              6200 Melton Rd, Portage
                2.5 out of 5.0
                 
                 

                Located in the business district, this family-friendly hotel is within 12 mi (20 km) of Indiana University Northwest, Deep River Water Park, and Indiana Dunes ...

                Best Western Plus Portage Hotel & Suites$84

                Best Western Plus Portage Hotel & Suites$84
                Chicago Lake Shore Hotel

                Chicago Lake Shore Hotel

                4900 S Lake Shore Dr, Chicago
                  3.0 out of 5.0
                   
                   

                  Located 5 miles south of downtown Chicago, this hotel is also just south of McCormick Place and overlooks Lake Michigan.

                  Chicago Lake Shore Hotel$83

                  Chicago Lake Shore Hotel$83
                  Extended Stay America Merrillville - US Rte. 30

                  Extended Stay America Merrillville - US Rte. 30

                  1355 E 83rd Ave, Merrillville
                    2.5 out of 5.0
                     
                     

                    Situated in Merrillville, this hotel is 1.5 mi (2.5 km) from Star Plaza Theatre and within 9 mi (15 km) of Deep River Water Park and Indiana University Northwest. ...

                    Extended Stay America Merrillville - US Rte. 30$72

                    Extended Stay America Merrillville - US Rte. 30$72
                    La Quinta Inn Merrillville

                    La Quinta Inn Merrillville

                    8210 Louisiana St, Merrillville
                      2.5 out of 5.0
                       
                       

                      Situated in Merrillville, this hotel is 1.4 mi (2.3 km) from Star Plaza Theatre and within 9 mi (15 km) of Deep River Water Park and Indiana University Northwest. ...

                      La Quinta Inn Merrillville$64

                      La Quinta Inn Merrillville$64

                      Top Flight Deals

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