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Vacation Rentals in Chicago

See all Vacation Rentals in Chicago
Pangea Suites

Pangea Suites

55 E Washington Street, Chicago
    3.5 out of 5.0
     
     
    2.5 out of 5 (2 reviews)

    Located in The Loop, this aparthotel is steps from Michigan Avenue, Millennium Park, and Chicago Cultural Center. Art Institute of Chicago and Chicago Theatre ...

    Pittsfield Apartments + Suites

    Pittsfield Apartments + Suites

    55 E Washington St., Chicago
      3.0 out of 5.0
       
       
      2.4 out of 5 (10 reviews)

      Located in The Loop, this apartment building is steps from Michigan Avenue, Millennium Park, and Chicago Cultural Center. Art Institute of Chicago and Chicago ...

      Pittsfield Apartments + Suites$48

      Comfort Suites Michigan Avenue Loop

      Comfort Suites Michigan Avenue Loop

      320 N. Michigan Avenue, Chicago
        3.0 out of 5.0
         
         
        4.3 out of 5 (37 reviews)

        Located in The Loop, this aparthotel is within a 5-minute walk of Michigan Avenue and Wrigley Building. Millennium Park and Chicago Theatre are also within 10 ...

        Comfort Suites Michigan Avenue Loop$89

        Dewitt Hotel and Suites

        Dewitt Hotel and Suites

        900 N Dewitt Pl, Chicago
          3.0 out of 5.0
           
           
          3.7 out of 5 (9 reviews)

          Located in Near North Side, this aparthotel is within a 5-minute walk of Magnificent Mile and John Hancock Center. Chicago Water Tower and Tribune Tower are ...

          Dewitt Hotel and Suites$67

          Ginosi 747 Apartel

          Ginosi 747 Apartel

          747 N May St., Chicago
            2.5 out of 5.0
             
             

            Located in West Town, this apartment building is within 2 mi (3 km) of Magnificent Mile, John Hancock Center, and Merchandise Mart. United Center and Chicago ...

            Ginosi 747 Apartel$48

            River North Waterside Condos

            River North Waterside Condos

            West Hubbard St and N Wells Street, Chicago
               
               

              Located in River North, this apartment building is 0.1 mi (0.1 km) from Magnificent Mile.

              Residence Inn Marriott Chicago Midway

              Residence Inn Marriott Chicago Midway

              6638 S Cicero Ave, Chicago
                3.0 out of 5.0
                 
                 
                4.8 out of 5 (8 reviews)

                Situated near the airport, this aparthotel is within 9 mi (15 km) of Toyota Park, University of Chicago, and State Street. Douglas Park and University of Chicago ...

                Residence Inn Marriott Chicago Midway$135

                Oakwood 200 Squared

                Oakwood 200 Squared

                210 North Wells Street, Chicago
                  4.0 out of 5.0
                   
                   
                  5.0 out of 5 (1 reviews)

                  Located in The Loop, this apartment building is within a 5-minute walk of Chicago Riverwalk and Merchandise Mart. Ford Center for the Performing Arts Oriental ...

                  Oakwood 200 Squared$89

                  West Town Guest House

                  West Town Guest House

                  1413 N Ashland Ave, Chicago
                    3.0 out of 5.0
                     
                     

                    Located in Wicker Park, this apartment building is within 3 mi (5 km) of Concord Music Hall, John Hancock Center, and Willis Tower. Skydeck Ledge and University ...

                    West Town Guest House$29

                    River North Luxe Condos

                    River North Luxe Condos

                    West Erie Street and North Dearborn St , Chicago
                       
                       

                      Located in River North, this apartment building is within a 10-minute walk of Magnificent Mile and Chicago Water Tower. John Hancock Center and Tribune Tower ...

                      Corporate Suites in the Heart of Magnificent Mile

                      Corporate Suites in the Heart of Magnificent Mile

                      East Ohio Street & North Michigan Avenue, Chicago
                        3.5 out of 5.0
                         
                         
                        4.3 out of 5 (3 reviews)

                        Located in Near North Side, this apartment building is steps from Magnificent Mile and Tribune Tower. John Hancock Center and Wrigley Building are also within ...

                        WoodSpring Suites Chicago Tinley Park

                        WoodSpring Suites Chicago Tinley Park

                        18636 West Creek Drive, Tinley Park
                          2.5 out of 5.0
                           
                           
                          3.0 out of 5 (1 reviews)

                          Situated in the business district, this aparthotel is 1 mi (1.6 km) from Tinley Park Convention Center and 2.9 mi (4.7 km) from Hollywood Casino Amphitheatre. ...

                          WoodSpring Suites Chicago Tinley Park$90

                          Apartments in the Loop

                          Apartments in the Loop

                          N Franklin St and West Calhoun Pl , Chicago
                             
                             

                            Located in The Loop, this apartment building is within a 10-minute walk of Chicago City Hall, Willis Tower, and Skydeck Ledge. Ford Center for the Performing ...

                            Residence Inn by Marriott Chicago Naperville/Warrenville

                            Residence Inn by Marriott Chicago Naperville/Warrenville

                            28500 Bella Vista Parkway, Warrenville
                              3.0 out of 5.0
                               
                               
                              4.5 out of 5 (4 reviews)

                              Situated in the business district, this aparthotel is within 9 mi (15 km) of Morton Arboretum, College of Dupage, and Wheaton College. Chicago Premium Outlets ...

                              Residence Inn by Marriott Chicago Naperville/Warrenville$84

                              Sunny Lakeview Suites by Sonder

                              Sunny Lakeview Suites by Sonder

                              North Clark Street, Belmont Ave, Chicago
                                3.5 out of 5.0
                                 
                                 

                                This apartment building is located in Chicago (Lakeview), close to Vic Theatre, Wrigley Field, and Lincoln Park. Also nearby are Lincoln Park Zoo and Kingston ...

                                Grand Local Ave Luxury Apartments

                                Grand Local Ave Luxury Apartments

                                1411 W Grand Ave, Chicago
                                  3.5 out of 5.0
                                   
                                   

                                  Located in West Town, this apartment building is within 2 mi (3 km) of Union Park, United Center, and Merchandise Mart. University of Illinois Chicago and Willis ...

                                  Grand Local Ave Luxury Apartments$122

                                  Lakeview Apartments in Chicago

                                  Lakeview Apartments in Chicago

                                  734 W Sheridan Rd, Chicago
                                    3.5 out of 5.0
                                     
                                     

                                    This apartment building is located in Chicago (Lakeview), close to Lincoln Park, Wrigley Field, and Vic Theatre. Also nearby are Saint Joseph Hospital and Kingston ...

                                    The Plymouth Premier 2BR Suites by Sonder

                                    The Plymouth Premier 2BR Suites by Sonder

                                    South Dearborn Street, Chicago
                                      4.0 out of 5.0
                                       
                                       

                                      This apartment building is located in Chicago (The Loop), close to Roosevelt University, Art Institute of Chicago, and Willis Tower. Also nearby are Skydeck ...

                                      The Penthouse at Grand Plaza

                                      The Penthouse at Grand Plaza

                                      540 North State Street, Near North Side, Chicago
                                        4.0 out of 5.0
                                         
                                         

                                        Located in River North, this apartment building is within a 10-minute walk of Magnificent Mile, Tribune Tower, and Wrigley Building. John Hancock Center and ...

                                        Apartment in River North with Balcony

                                        Apartment in River North with Balcony

                                        750 North Hudson Avenue, Chicago
                                          3.5 out of 5.0
                                           
                                           

                                          Located in River North, this apartment building is within 1 mi (2 km) of Magnificent Mile, John Hancock Center, and Merchandise Mart. Willis Tower and Skydeck ...

                                          Map

                                          Chicago is a city with many nicknames. The Windy City’s impressive skyline glitters across Lake Michigan, inspiring Carl Sandburg to dub it the City of Big Shoulders when it became the birthplace of the skyscraper. As the home of a rich Blues music tradition, Chicago has also been called Toddlin’ Town and Sweet Home Chicago by voices such as Frank Sinatra and Robert Johnson. Get to know the many names of faces of this great city like a local from our Chicago vacation rentals.

                                          The Local Life

                                          Locals know that exploring Chicago’s best kept secrets is about digging deeper. Sure, try the obligatory Chicago dog, but then head to that corner gourmet dog store for something completely unique, like a chicken, apple, and cranberry dog. Go ahead, wolf it down. We won’t judge.

                                          Enjoy views of famous buildings such as the John Hancock Center, Tribune Tower, and Chicago Water Tower, or be part of the skyline at Embassy Suites Chicago Downtown Magnificent Mile. Locals love the area because it’s so close to the Chicago Riverwalk and the famous Millennium Park.

                                          The Chicago Institute of Art draws admirers from around the world, but the Museum of Contemporary Photography and the Chicago Cultural Center provide inspiration for those who are willing to venture off the beaten path. Luckily, the Ginosi Basics Loop Apartel is close by and features a classy lobby that’s photogenic enough for your own photography exhibit on social media. You can call that shot Untitled #4, or simply #Chicagovacation.

                                          See a side of Chicago most visitors miss, then relax in one of Travelocity’s vacation rentals, where it feels like Sweet Home Chicago.