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Vacation Rentals in Chicago

See all Vacation Rentals in Chicago
Pangea Corporate Suites

Pangea Corporate Suites

55 E Washington Street, Chicago
    3.5 out of 5.0
     
     
    2.5 out of 5 (17 reviews)

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

    Pangea Corporate Suites$49

    Pangea Corporate Suites$49
    Pittsfield Apartments + Suites

    Pittsfield Apartments + Suites

    55 E Washington St., Chicago
      3.0 out of 5.0
       
       
      3.0 out of 5 (746 reviews)

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

      Pittsfield Apartments + Suites$64

      Pittsfield Apartments + Suites$64
      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 (1,654 reviews)

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

        Comfort Suites Michigan Avenue Loop$99

        Comfort Suites Michigan Avenue Loop$99
        Dewitt Hotel and Suites

        Dewitt Hotel and Suites

        900 N Dewitt Pl, Chicago
          3.0 out of 5.0
           
           
          3.8 out of 5 (914 reviews)

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

          Dewitt Hotel and Suites$76

          Dewitt Hotel and Suites$76
          Ginosi 747 Apartel

          Ginosi 747 Apartel

          747 N May St., Chicago
            2.5 out of 5.0
             
             
            4.5 out of 5 (31 reviews)

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

            Ginosi 747 Apartel$100

            Ginosi 747 Apartel$100
            River North Waterside Condos

            River North Waterside Condos

            West Hubbard St and N Wells Street, Chicago
               
               
              4.5 out of 5 (8 reviews)

              Located in River North, this apartment building is steps from Downtown Chicago and Magnificent Mile.

              River North Waterside CondosGet Rates

              River North Waterside CondosGet Rates
              Residence Inn Marriott Chicago Midway

              Residence Inn Marriott Chicago Midway

              6638 S Cicero Ave, Chicago
                 
                 
                4.5 out of 5 (227 reviews)

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

                Residence Inn Marriott Chicago Midway$158

                Residence Inn Marriott Chicago Midway$158
                Oakwood 200 Squared

                Oakwood 200 Squared

                210 North Wells Street, Chicago
                  4.0 out of 5.0
                   
                   
                  4.6 out of 5 (85 reviews)

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

                  Oakwood 200 Squared$169

                  Oakwood 200 Squared$169
                  West Town Guest House

                  West Town Guest House

                  1413 N Ashland Ave, Chicago
                    3.0 out of 5.0
                     
                     
                    3.9 out of 5 (12 reviews)

                    Located in Wicker Park, this apartment building is 1.2 mi (1.9 km) from Downtown Chicago and within 3 mi (5 km) of John Hancock Center and Willis Tower. Skydeck ...

                    West Town Guest HouseGet Rates

                    West Town Guest HouseGet Rates
                    River North Luxe Condos

                    River North Luxe Condos

                    West Erie Street and North Dearborn St , Chicago
                       
                       
                      5.0 out of 5 (2 reviews)

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

                      River North Luxe CondosGet Rates

                      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 (35 reviews)

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

                        Corporate Suites in the Heart of Magnificent MileGet Rates

                        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 (58 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$80

                          WoodSpring Suites Chicago Tinley Park$80
                          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
                            Apartments in the Loop

                            Apartments in the Loop

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

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

                              Apartments in the LoopGet Rates

                              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
                                 
                                 
                                4.3 out of 5 (131 reviews)

                                Situated in the business district, this aparthotel is within 3 mi (5 km) of Arrowhead Golf Club, DuPage Children's Museum, and Saints Peter and Paul Catholic ...

                                Residence Inn by Marriott Chicago Naperville/Warrenville$98

                                Residence Inn by Marriott Chicago Naperville/Warrenville$98
                                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 ...

                                  Sunny Lakeview Suites by SonderGet Rates

                                  Sunny Lakeview Suites by SonderGet Rates
                                  Lakeview Apartments in Chicago

                                  Lakeview Apartments in Chicago

                                  734 W Sheridan Rd, Chicago
                                    3.5 out of 5.0
                                     
                                     
                                    4.0 out of 5 (1 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

                                    Lakeview Apartments in ChicagoGet Rates
                                    The Plymouth Premier 2BR Suites by Sonder

                                    The Plymouth Premier 2BR Suites by Sonder

                                    South Dearborn Street, Chicago
                                       
                                       

                                      Located in The Loop, this apartment building is 0.1 mi (0.1 km) from Downtown Chicago.

                                      The Plymouth Premier 2BR Suites by SonderGet Rates

                                      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 Downtown Chicago, Tribune Tower, and Wrigley Building. John Hancock Center and ...

                                        The Penthouse at Grand PlazaGet Rates

                                        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 Downtown Chicago, John Hancock Center, and Merchandise Mart. Willis Tower and Skydeck ...

                                          Apartment in River North with BalconyGet Rates

                                          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
                                            3.0 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$106

                                            Congress Plaza Hotel$106
                                            Palmer House a Hilton Hotel

                                            Palmer House a Hilton Hotel

                                            17 E Monroe St, Chicago
                                               
                                               

                                              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$90

                                              Palmer House a Hilton Hotel$90
                                              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$121

                                                Freehand Chicago$121
                                                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