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Highland Park Vacations

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

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

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 Park 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 Park well.

Highland Park Flight + Hotel packages

Top Hotel Deals

See all 456 Hotels in Highland Park
Courtyard Chicago Highland Park/Northbrook

Courtyard Chicago Highland Park/Northbrook

1505 Lake Cook Road, Highland Park
    3.0 out of 5.0
     
     

    Situated in the suburbs, this hotel is 0.7 mi (1.2 km) from Chicago Botanic Garden and within 3 mi (5 km) of Ravinia Park and Ravinia Pavillion. Rosewood Beach ...

    Courtyard Chicago Highland Park/Northbrook$94

    Courtyard Chicago Highland Park/Northbrook$94
    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$89

      Edward Hotel Chicago$89
      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
            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$72

              Country Inn & Suites by Radisson, Chicago O'Hare South, IL$72
              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
                Hotel Versey Days Inn by Wyndham Chicago

                Hotel Versey Days Inn by Wyndham Chicago

                644 West Diversey Parkway, Chicago
                  3.0 out of 5.0
                   
                   

                  In Chicago's lively Lakeview neighborhood, this award-winning Days Inn is about 1 mile from Lincoln Park, the Lincoln Park Zoo, Wrigley Field, and the Peggy ...

                  Hotel Versey Days Inn by Wyndham Chicago$93

                  Hotel Versey Days Inn by Wyndham Chicago$93
                  Chicago Getaway Hostel

                  Chicago Getaway Hostel

                  616 W Arlington Pl, Chicago
                    1.5 out of 5.0
                     
                     

                    Located in Lincoln Park, this hostel is within 1 mi (2 km) of Lincoln Hall and Lincoln Park Zoo. Wrigley Field and John Hancock Center are also within 3 mi (5 ...

                    Hotel Lincoln

                    Hotel Lincoln

                    1816 N Clark Street, Chicago
                      4.0 out of 5.0
                       
                       

                      Located in Lincoln Park, this boutique hotel is within a 10-minute walk of Second City, Chicago History Museum, and Lincoln Park Zoo. North Avenue Beach and ...

                      Hotel Lincoln$129

                      Hotel Lincoln$129

                      Top Flight Deals

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