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Highland Hills Vacations

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

Hotwire can help you find your travel bliss with Highland Hills 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 Hills

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 Hills 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 Hills well.

Top Hotel Deals

See all 518 Hotels in Highland Hills
SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street, Lombard
    2.5 out of 5.0
     
     

    Situated in the suburbs, this hotel is 0.8 mi (1.3 km) from Yorktown Shopping Center and within 6 mi (10 km) of Lilacia Park and Drury Lane Theater. Belmont ...

    SureStay Plus Hotel by Best Western Chicago Lombard$60

    SureStay Plus Hotel by Best Western Chicago Lombard$60
    Extended Stay America - Chicago - Lombard - Yorktown Center

    Extended Stay America - Chicago - Lombard - Yorktown Center

    260 E 22nd St, Lombard
      2.5 out of 5.0
       
       

      Situated in a shopping district, this hotel is 0.8 mi (1.3 km) from Yorktown Shopping Center and within 6 mi (10 km) of Lilacia Park and Drury Lane Theater. ...

      Extended Stay America - Chicago - Lombard - Yorktown Center$76

      Extended Stay America - Chicago - Lombard - Yorktown Center$76
      Sonesta ES Suites Chicago - Lombard

      Sonesta ES Suites Chicago - Lombard

      2001 S Highland Avenue, Lombard
        3.0 out of 5.0
         
         

        Situated in Highland Hills, this hotel is 0.8 mi (1.3 km) from Yorktown Shopping Center and within 6 mi (10 km) of Lilacia Park and Drury Lane Theater. Belmont ...

        Sonesta ES Suites Chicago - Lombard$109

        Sonesta ES Suites Chicago - Lombard$109
        Edward Hotel Chicago

        Edward Hotel Chicago

        6600 N. Mannheim Rd, Rosemont
          3.0 out of 5.0
           
           

          Situated near the airport, this hotel is 0.4 mi (0.6 km) from Allstate Arena and within 3 mi (5 km) of Rivers Casino and Donald E. Stephens Convention Center. ...

          Edward Hotel Chicago$81

          Edward Hotel Chicago$81
          Hotel Chicago West Loop

          Hotel Chicago West Loop

          1622 W Jackson Blvd, Chicago
            2.5 out of 5.0
             
             

            Located in Near West Side, this hotel is within 2 mi (3 km) of United Center, University of Illinois Chicago, and Willis Tower. Skydeck Ledge and Art Institute ...

            Hotel Chicago West Loop$71

            Hotel Chicago West Loop$71
            Best Western At O'Hare

            Best Western At O'Hare

            10300 W Higgins Road, Rosemont
              3.0 out of 5.0
               
               

              This hotel is 4 blocks from Allstate Arena (DePaul Blue Demons; Chicago Wolves) and 2 miles from O'Hare Airport; complimentary 24-hour shuttle service is ...

              Best Western At O'Hare$69

              Best Western At O'Hare$69
              Hyatt Place Chicago/O'Hare Airport

              Hyatt Place Chicago/O'Hare Airport

              6810 Mannheim Rd, Rosemont
                3.0 out of 5.0
                 
                 

                Situated near the airport, this hotel is 0.2 mi (0.3 km) from Allstate Arena and within 3 mi (5 km) of Rivers Casino and Donald E. Stephens Convention Center. ...

                Hyatt Place Chicago/O'Hare Airport$113

                Hyatt Place Chicago/O'Hare Airport$113
                Red Roof Inn Chicago - O'Hare Airport

                Red Roof Inn Chicago - O'Hare Airport

                22 West Algonquin Road, Arlington Heights
                  2.0 out of 5.0
                   
                   

                  Situated near the airport, this motel is 1.1 mi (1.8 km) from Heritage Park and within 3 mi (5 km) of Arlington Lakes Golf Club and Metropolis Performing Arts ...

                  Red Roof Inn Chicago - O'Hare Airport$43

                  Red Roof Inn Chicago - O'Hare Airport$43
                  Loews Chicago O'Hare Hotel

                  Loews Chicago O'Hare Hotel

                  5300 N River Rd, Rosemont
                    4.5 out of 5.0
                     
                     

                    This family-friendly Rosemont hotel is located near the airport, within a 10-minute walk of Rosemont Theatre, Fashion Outlets of Chicago, and Donald E. Stephens ...

                    Loews Chicago O'Hare Hotel$103

                    Loews Chicago O'Hare Hotel$103
                    Country Inn & Suites by Radisson, Chicago O'Hare South, IL

                    Country Inn & Suites by Radisson, Chicago O'Hare South, IL

                    777 East Grand Avenue, Bensenville
                      3.0 out of 5.0
                       
                       

                      Situated near the airport, this hotel is within 9 mi (15 km) of Stevenson Park, Rosemont Theatre, and MB Financial Park at Rosemont. Fashion Outlets of Chicago ...

                      Country Inn & Suites by Radisson, Chicago O'Hare South, IL$76

                      Country Inn & Suites by Radisson, Chicago O'Hare South, IL$76

                      Top Flight Deals

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