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Near North Side Vacations

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

Hotwire can help you find your travel bliss with Near North 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 North 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 North 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 North Side well.

Near North Side Flight + Hotel packages

Top Hotel Deals

See all 130 Hotels in Near North Side
Warwick Allerton - Chicago

Warwick Allerton - Chicago

701 North Michigan Avenue, Chicago
    4.0 out of 5.0
     
     

    Located on Michigan Avenue in the middle of Chicago's Magnificent Mile, this 1920s Italian Renaissance hotel is surrounded by fashionable shops, 1 mile from ...

    Warwick Allerton - Chicago$91

    Warwick Allerton - Chicago$91
    Trump International Hotel & Tower Chicago

    Trump International Hotel & Tower Chicago

    401 N Wabash Ave, Chicago
      5.0 out of 5.0
       
       

      Located in Near North Side, this family-friendly Chicago hotel is within a 5-minute walk of Wrigley Building and Tribune Tower. Chicago Theatre and Ford Center ...

      Trump International Hotel & Tower Chicago$310

      Trump International Hotel & Tower Chicago$310
      The James Chicago-Magnificent Mile

      The James Chicago-Magnificent Mile

      55 East Ontario Street, Chicago
        4.5 out of 5.0
         
         

        Right on Magnificent Mile, The James Chicago-Magnificent Mile puts guests in the middle of Chicago's famed shopping district filled with boutiques and restaurants. ...

        The James Chicago-Magnificent Mile$137

        The James Chicago-Magnificent Mile$137
        Embassy Suites Chicago Downtown Magnificent Mile

        Embassy Suites Chicago Downtown Magnificent Mile

        511 North Columbus Drive, Chicago
          4.0 out of 5.0
           
           

          The Embassy Suites Chicago Downtown Lakefront offers a newly renovated fresh look and is located two blocks from Navy Pier, Magnificent Mile shopping, and within ...

          Embassy Suites Chicago Downtown Magnificent Mile$159

          Embassy Suites Chicago Downtown Magnificent Mile$159
          Millennium Knickerbocker Chicago

          Millennium Knickerbocker Chicago

          163 East Walton Place, Chicago
            4.0 out of 5.0
             
             

            This 1927 landmark Chicago hotel is a half block from Michigan Avenue/Magnificent Mile shopping, two blocks from Oak Street shopping and Water Tower Place. Lake ...

            Millennium Knickerbocker Chicago$97

            Millennium Knickerbocker Chicago$97
            Sofitel Chicago Magnificent Mile

            Sofitel Chicago Magnificent Mile

            20 E Chestnut St, Chicago
              4.5 out of 5.0
               
               

              Located 1 block from Rush Street nightclubs, Oak Street shopping, and the Magnificent Mile, this 32-story Gold Coast hotel is 2 blocks from the John Hancock ...

              Sofitel Chicago Magnificent Mile$167

              Sofitel Chicago Magnificent Mile$167
              Viceroy Chicago

              Viceroy Chicago

              1118 North State Street, Chicago
                4.5 out of 5.0
                 
                 

                This hotel is located in Chicago (Near North Side), close to Magnificent Mile, John Hancock Center, and Chicago Water Tower. Also nearby are Millennium Park ...

                Viceroy Chicago$172

                Viceroy Chicago$172
                The Godfrey Hotel Chicago

                The Godfrey Hotel Chicago

                127 West Huron, at LaSalle, Chicago
                  4.5 out of 5.0
                   
                   

                  Located in Near North Side, this spa hotel is within a 15-minute walk of Holy Name Cathedral, John Hancock Center, and Chicago Water Tower. Merchandise Mart ...

                  The Godfrey Hotel Chicago$113

                  The Godfrey Hotel Chicago$113
                  Hyatt Place Chicago/River North

                  Hyatt Place Chicago/River North

                  66 W Illinois St, Chicago
                    3.0 out of 5.0
                     
                     

                    Three blocks from the river, Hyatt Place Chicago/River North is on a lively street in downtown Chicago. It's just north of the corporate hub, The Loop, and a ...

                    Hyatt Place Chicago/River North$136

                    Hyatt Place Chicago/River North$136
                    The Whitehall Hotel

                    The Whitehall Hotel

                    105 E Delaware Pl, Chicago
                      4.0 out of 5.0
                       
                       

                      Built in 1927, this Chicago hotel is one block from Michigan Avenue shopping and Rush Street restaurants and nightlife; Lake Michigan is within five blocks.

                      The Whitehall Hotel$98

                      The Whitehall Hotel$98

                      Top Flight Deals

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