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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
     
     
    2.4 out of 5 (38 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 ...

    Pangea SuitesGet Rates

    Pittsfield Apartments + Suites

    Pittsfield Apartments + Suites

    55 E Washington St., Chicago
      3.0 out of 5.0
       
       
      3.0 out of 5 (781 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$51

      Pittsfield Apartments + Suites$51
      Comfort Suites Michigan Avenue Loop

      Comfort Suites Michigan Avenue Loop

      320 N. Michigan Avenue, Chicago
        3.0 out of 5.0
         
         
        4.2 out of 5 (1,710 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

        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
           
           
          3.8 out of 5 (943 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

          Dewitt Hotel and Suites$67
          Ginosi 747 Apartel

          Ginosi 747 Apartel

          747 N May St., Chicago
            2.5 out of 5.0
             
             
            4.2 out of 5 (47 reviews)

            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$45

            Ginosi 747 Apartel$45
            River North Waterside Condos

            River North Waterside Condos

            West Hubbard St and N Wells Street, Chicago
               
               
              4.6 out of 5 (21 reviews)

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

              River North Waterside CondosGet Rates

              Residence Inn Marriott Chicago Midway

              Residence Inn Marriott Chicago Midway

              6638 S Cicero Ave, Chicago
                3.0 out of 5.0
                 
                 
                4.5 out of 5 (234 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$148

                Residence Inn Marriott Chicago Midway$148
                Oakwood 200 Squared

                Oakwood 200 Squared

                210 North Wells Street, Chicago
                  4.0 out of 5.0
                   
                   
                  4.6 out of 5 (99 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

                  Oakwood 200 Squared$89
                  West Town Guest House

                  West Town Guest House

                  1413 N Ashland Ave, Chicago
                    3.0 out of 5.0
                     
                     
                    3.5 out of 5 (17 reviews)

                    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

                    West Town Guest House$29
                    River North Luxe Condos

                    River North Luxe Condos

                    West Erie Street and North Dearborn St , Chicago
                       
                       
                      4.7 out of 5 (6 reviews)

                      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 ...

                      River North Luxe CondosGet Rates

                      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
                         
                         
                        3.9 out of 5 (40 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 ...

                        Corporate Suites in the Heart of Magnificent MileGet Rates

                        WoodSpring Suites Chicago Tinley Park

                        WoodSpring Suites Chicago Tinley Park

                        18636 West Creek Drive, Tinley Park
                          2.5 out of 5.0
                           
                           
                          3.7 out of 5 (71 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

                          WoodSpring Suites Chicago Tinley Park$90
                          Apartments in the Loop

                          Apartments in the Loop

                          N Franklin St and West Calhoun Pl , Chicago
                             
                             
                            4.2 out of 5 (8 reviews)

                            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 ...

                            Apartments in the LoopGet Rates

                            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
                               
                               
                              4.2 out of 5 (134 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

                              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
                                 
                                 
                                5.0 out of 5 (1 reviews)

                                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 ...

                                Sunny Lakeview Suites by SonderGet Rates

                                Grand Local Ave Luxury Apartments

                                Grand Local Ave Luxury Apartments

                                1411 W Grand Ave, Chicago
                                  3.5 out of 5.0
                                   
                                   
                                  4.1 out of 5 (12 reviews)

                                  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

                                  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
                                     
                                     
                                    2.5 out of 5 (2 reviews)

                                    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 ...

                                    Lakeview Apartments in ChicagoGet Rates

                                    The Plymouth Premier 2BR Suites by Sonder

                                    The Plymouth Premier 2BR Suites by Sonder

                                    South Dearborn Street, Chicago
                                      4.0 out of 5.0
                                       
                                       
                                      1.0 out of 5 (1 reviews)

                                      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 Plymouth Premier 2BR Suites by SonderGet Rates

                                      The Penthouse at Grand Plaza

                                      The Penthouse at Grand Plaza

                                      540 North State Street, Near North Side, Chicago
                                        4.0 out of 5.0
                                         
                                         
                                        5.0 out of 5 (11 reviews)

                                        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 ...

                                        The Penthouse at Grand PlazaGet Rates

                                        Apartment in River North with Balcony

                                        Apartment in River North with Balcony

                                        750 North Hudson Avenue, Chicago
                                          3.5 out of 5.0
                                           
                                           
                                          4.3 out of 5 (3 reviews)

                                          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 ...

                                          Apartment in River North with BalconyGet Rates

                                          Map

                                          Choosing the perfect Chicago (and vicinity) rental

                                          You've likely stayed at countless hotels. Maybe it's time to try a vacation rental to experience the area like a local. Stay in Chicago (and vicinity) at one of 26 vacation rentals now bookable on Expedia.com.

                                          • 22 apartments
                                          • 4 condos

                                          Shoppers, art connoisseurs, and foodies are in for a treat, while all visitors will find something at this urban lakeside destination to delight in. Families won't want to miss the nearby concerts and theaters.

                                          Dining in Chicago (and vicinity)

                                          Ada Street, University Club of Chicago, and Maria's Packaged Goods and Community Bar are a few favorite spots to grab some food. Most vacation rentals come with full-size kitchens, so eating in is always an option, too.

                                          Sightseeing around Chicago (and vicinity)

                                          Some of the top sights in Chicago (and vicinity) include Millennium Park, Willis Tower, and Skydeck Ledge. If you're bringing the kiddos along, save a few hours for Six Flags Great America, Navy Pier, and John G. Shedd Aquarium. Culture aficionados will have plenty to take in at Chicago Cultural Center, Ford Center for the Performing Arts Oriental Theatre, and Chicago Theater. If your vacation agenda includes shopping, consider a trip to Chicago Premium Outlets and Shops at Northbridge. Outdoor enthusiasts will appreciate a jaunt through Grant Park and Lincoln Park.

                                          Exploring the Chicago (and vicinity) area

                                          For those arriving without a car, nearby metro stations like Monroe Station, Monroe Station, or Adams-Wabash Station provide a convenient transportation option. To travel outside the immediate area, consider taking a train from Millennium Station, Chicago Van Buren Street Station, or Chicago Union Station.

                                          Packing for your Chicago (and vicinity) trip

                                          Wondering what the weather will be like on your trip? Here are the seasonal average temperatures.

                                          • January–March: 31°F
                                          • April–June: 61°F
                                          • July–September: 72°F
                                          • October–December: 42°F

                                          Booking your rental on Expedia

                                          Expedia makes it easy and safe to book vacation rentals in Chicago (and vicinity). We can even help you contact the property owner to make special arrangements. You're sure to have a memorable trip with the convenience of a short-term rental.

                                          Other types of properties in Chicago you may be interested in

                                          Congress Plaza Hotel

                                          Congress Plaza Hotel

                                          520 South Michigan Avenue, Chicago
                                            3.5 out of 5.0
                                             
                                             

                                            Built in 1893, this downtown Chicago hotel offers a convenient location across from Grant Park and close to Lake Michigan.

                                            Congress Plaza Hotel$79

                                            Congress Plaza Hotel$79
                                            Palmer House a Hilton Hotel

                                            Palmer House a Hilton Hotel

                                            17 E Monroe St, Chicago
                                              4.0 out of 5.0
                                               
                                               

                                              This 1925 Beaux Arts-style Chicago hotel is steps from Millennium Park, 2 blocks from Macy's and the Art Institute, and 1 mile from Lake Michigan, Magnificent ...

                                              Palmer House a Hilton Hotel$92

                                              Palmer House a Hilton Hotel$92
                                              Freehand Chicago

                                              Freehand Chicago

                                              19 East Ohio Street, Chicago
                                                3.5 out of 5.0
                                                 
                                                 

                                                Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Museum of Contemporary ...

                                                Freehand Chicago$77

                                                Freehand Chicago$77
                                                Comfort Inn Arlington Heights - O'Hare

                                                Comfort Inn Arlington Heights - O'Hare

                                                2120 S Arlington Heights Rd, Arlington Heights
                                                  2.5 out of 5.0
                                                   
                                                   

                                                  Situated near the airport, this hotel is within 1 mi (2 km) of Ned Brown Forest Preserve and Heritage Park. Arlington Lakes Golf Club and Metropolis Performing ...

                                                  Comfort Inn Arlington Heights - O'Hare$68

                                                  Comfort Inn Arlington Heights - O'Hare$68