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Streeterville Vacations

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

Hotwire can help you find your travel bliss with Streeterville 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 Streeterville

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 Streeterville 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 Streeterville well.

Top Hotel Deals

See all 608 Hotels in Streeterville
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$99

    Warwick Allerton - Chicago$99
    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 Magnificent Mile offers a newly renovated fresh look and is located two blocks from Navy Pier, Magnificent Mile shopping, ...

      Embassy Suites Chicago Downtown Magnificent Mile$169

      Embassy Suites Chicago Downtown Magnificent Mile$169
      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$110

        Millennium Knickerbocker Chicago$110
        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$89

          The Whitehall Hotel$89
          W Chicago - Lakeshore

          W Chicago - Lakeshore

          644 N Lake Shore Dr, Chicago
            4.5 out of 5.0
             
             

            The luxury W Chicago - Lakeshore overlooks Lake Michigan and is just steps away from Chicago's iconic attractions, including Ohio Street Beach, Navy Pier, and ...

            W Chicago - Lakeshore$112

            W Chicago - Lakeshore$112
            Sheraton Grand Chicago

            Sheraton Grand Chicago

            301 E North Water St, Chicago
              4.0 out of 5.0
               
               

              This 34-story Chicago hotel is three blocks from Michigan Avenue shopping, the Navy Pier, and Lake Michigan; the Loop business district and the Wrigley Building ...

              Sheraton Grand Chicago$139

              Sheraton Grand Chicago$139
              AC Hotels by Marriott Chicago Downtown

              AC Hotels by Marriott Chicago Downtown

              630 N Rush St, Chicago
                3.5 out of 5.0
                 
                 

                This hotel is just off the Magnificent Mile and one-third mile from Water Tower Place and the Wrigley Building. Millennium Park is 0.7 mile from the hotel; the ...

                AC Hotels by Marriott Chicago Downtown$112

                AC Hotels by Marriott Chicago Downtown$112
                Omni Chicago Suites - Magnificent Mile

                Omni Chicago Suites - Magnificent Mile

                676 N Michigan Ave, Chicago
                  4.5 out of 5.0
                   
                   

                  Omni Chicago Suites - Magnificent Mile is at the center of Chicago’s most prestigious neighborhood, 3 blocks from the shores of Lake Michigan and around the ...

                  Omni Chicago Suites - Magnificent Mile$179

                  Omni Chicago Suites - Magnificent Mile$179
                  Loews Chicago Hotel

                  Loews Chicago Hotel

                  455 North Park Drive, Chicago
                    4.5 out of 5.0
                     
                     

                    Located in Near North Side, this luxury hotel is within a 10-minute walk of Tribune Tower and Wrigley Building. Navy Pier and Chicago Children's Museum are also ...

                    Loews Chicago Hotel$159

                    Loews Chicago Hotel$159
                    Hampton Inn Chicago Downtown/Magnificent Mile

                    Hampton Inn Chicago Downtown/Magnificent Mile

                    160 E Huron Street, Chicago
                      2.5 out of 5.0
                       
                       

                      Located a half-block from prime Magnificent Mile Avenue shopping, this downtown Chicago 225-room high-rise is 3 blocks from Lake Michigan, 4 blocks from Water ...

                      Hampton Inn Chicago Downtown/Magnificent Mile$139

                      Hampton Inn Chicago Downtown/Magnificent Mile$139

                      Top Flight Deals

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