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Near South Side Vacations

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

Hotwire can help you find your travel bliss with Near South Side 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 Near South Side

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 Near South Side 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 Near South Side well.

Near South Side Flight + Hotel packages

Top Hotel Deals

See all 621 Hotels in Near South Side
Hyatt Regency McCormick Place

Hyatt Regency McCormick Place

2233 S Martin Luther King Dr, Chicago
    4.0 out of 5.0
     
     

    Connected via enclosed skybridge to the McCormick Place convention complex, the Hyatt Regency is adjacent to a Metro station, with easy access to Chicago's downtown ...

    Hyatt Regency McCormick Place$104

    Hyatt Regency McCormick Place$104
    Marriott Marquis Chicago

    Marriott Marquis Chicago

    2121 South Prairie Avenue, Chicago
      4.0 out of 5.0
       
       

      Located in Near South Side, this hotel is within 1 mi (2 km) of McCormick Place, Soldier Field, and Field Museum of Natural History. John G. Shedd Aquarium and ...

      Marriott Marquis Chicago$152

      Marriott Marquis Chicago$152
      Chicago Downtown Condo - Michigan Ave Suite ID #14-15

      Chicago Downtown Condo - Michigan Ave Suite ID #14-15

      1255 S. Michigan Avenue, Chicago
        2.5 out of 5.0
         
         

        Located in Near South Side, this condo building is within a 15-minute walk of Columbia College Chicago and Grant Park. Art Institute of Chicago and Millennium ...

        Furnished Suites in South Loop Chicago

        Furnished Suites in South Loop Chicago

        1333 S Wabash Ave, Chicago
          3.5 out of 5.0
           
           

          Located in Near South Side, this apartment building is within 1 mi (2 km) of Columbia College Chicago, Art Institute of Chicago, and McCormick Place. Grant Park ...

          The Wheeler Mansion

          The Wheeler Mansion

          2020 South Calumet Avenue, Chicago
            4.0 out of 5.0
             
             

            Located in Near South Side, this luxury hotel is within a 10-minute walk of McCormick Place, Glessner House Museum, and National Vietnam Veterans Art ...

            Stay Alfred Apartments on Wabash

            Stay Alfred Apartments on Wabash

            1333 S. Wabash Avenue, Chicago
              4.0 out of 5.0
               
               

              This apartment building is located in Chicago (Near South Side), close to Field Museum of Natural History, Soldier Field, and John G. Shedd Aquarium. Also nearby ...

              Home2 Suites by Hilton Chicago McCormick Place

              Home2 Suites by Hilton Chicago McCormick Place

              123 E. CERMAK ROAD, Chicago
                2.5 out of 5.0
                 
                 

                This hotel is located in Chicago (Near South Side), close to Wintrust Arena, McCormick Place, and Art Institute of Chicago. Also nearby are Soldier Field and ...

                Hilton Garden Inn Chicago McCormick Place

                Hilton Garden Inn Chicago McCormick Place

                123 East Cermak, Suite 300, Chicago
                  3.0 out of 5.0
                   
                   

                  This hotel is located in Chicago (Near South Side), close to Wintrust Arena, McCormick Place, and Art Institute of Chicago. Also nearby are Soldier Field and ...

                  Hampton Inn Chicago McCormick Place

                  Hampton Inn Chicago McCormick Place

                  111 E Cermak Rd, Chicago
                    2.5 out of 5.0
                     
                     

                    This hotel is located in Chicago (Near South Side), close to Wintrust Arena, McCormick Place, and Art Institute of Chicago. Also nearby are Soldier Field and ...

                    Loft-Style 2BR in South Loop by Sonder

                    Loft-Style 2BR in South Loop by Sonder

                    1545 S State St, Chicago
                      4.0 out of 5.0
                       
                       

                      Top Flight Deals

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