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Wheeling Vacations

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

Hotwire can help you find your travel bliss with Wheeling 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 Wheeling

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 Wheeling 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 Wheeling well.

Wheeling Flight + Hotel packages

Top Hotel Deals

See all 473 Hotels in Wheeling
The Westin Chicago North Shore

The Westin Chicago North Shore

601 N Milwaukee Ave, Wheeling
    4.0 out of 5.0
     
     

    This family-friendly Wheeling hotel is located in the suburbs, within 3 mi (5 km) of Heritage Park and Sportsman's Country Club. Northbrook Sports Complex and ...

    The Westin Chicago North Shore$119

    The Westin Chicago North Shore$119
    Ramada Plaza by Wyndham Chicago North Shore

    Ramada Plaza by Wyndham Chicago North Shore

    1090 South Milwaukee Avenue, Wheeling
      3.0 out of 5.0
       
       

      Situated in Wheeling, this hotel is within 3 mi (5 km) of River Trail Nature Center, Heritage Park, and Grove National Historic Landmark. Rob Roy Golf Course ...

      Ramada Plaza by Wyndham Chicago North Shore$59

      Ramada Plaza by Wyndham Chicago North Shore$59
      Olde Court Inn

      Olde Court Inn

      374 North Milwaukee Ave, Wheeling
        2.0 out of 5.0
         
         

        Situated near the airport, this motel is 1.3 mi (2.1 km) from Heritage Park and 2.5 mi (4 km) from Sportsman's Country Club. River Trail Nature Center and Raupp ...

        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$70

            Best Western At O'Hare$70
            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$76

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

                      Top Flight Deals

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