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Vacation Rentals in Chicago

See all Vacation Rentals in Chicago
Pittsfield Apartments + Suites

Pittsfield Apartments + Suites

55 E Washington St., Chicago
    3.0 out of 5.0
     
     
    3.1 out of 5 (850 reviews)

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

    Pittsfield Apartments + Suites$63

    Pittsfield Apartments + Suites$63
    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 (1,781 reviews)

      Located in The Loop, this aparthotel is steps from Chicago Riverwalk and Michigan Avenue. Art Institute of Chicago and Chicago Theatre are also within 6 mi (10 ...

      Comfort Suites Michigan Avenue Loop$79

      Comfort Suites Michigan Avenue Loop$79
      Dewitt Hotel and Suites

      Dewitt Hotel and Suites

      900 N Dewitt Pl, Chicago
        3.0 out of 5.0
         
         
        3.8 out of 5 (983 reviews)

        Located in Near North Side, this aparthotel is within 6 mi (10 km) of Broadway Playhouse, John Hancock Center, and Water Tower Place. Chicago Riverwalk and Navy ...

        Dewitt Hotel and Suites$71

        Dewitt Hotel and Suites$71
        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 (237 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

          Residence Inn Marriott Chicago Midway$135
          WoodSpring Suites Chicago Tinley Park

          WoodSpring Suites Chicago Tinley Park

          18636 West Creek Drive, Tinley Park
            2.5 out of 5.0
             
             
            3.6 out of 5 (86 reviews)

            Situated in the business district, this aparthotel is within 9 mi (15 km) of Tinley Park Convention Center, Hollywood Casino Amphitheatre, and Space Golf. Gaelic ...

            WoodSpring Suites Chicago Tinley Park$80

            WoodSpring Suites Chicago Tinley Park$80
            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 (143 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$71

              Residence Inn by Marriott Chicago Naperville/Warrenville$71
              Beautiful New Room in Chicagowith the Breakfast

              Beautiful New Room in Chicagowith the Breakfast

              Chicago
                 
                 

                Beautiful New Room in Chicagowith the Breakfast$30

                Beautiful New Room in Chicagowith the Breakfast$30
                Beautiful Garden Level Room

                Beautiful Garden Level Room

                Chicago
                   
                   

                  Beautiful Garden Level Room$30

                  Beautiful Garden Level Room$30
                  Pangea Suites

                  Pangea Suites

                  55 E Washington Street, Chicago
                    3.5 out of 5.0
                     
                     
                    2.4 out of 5 (86 reviews)

                    Located in The Loop, this aparthotel is steps from Chicago Cultural Center and Millennium Park. Art Institute of Chicago and Chicago Riverwalk are also within ...

                    Pangea Suites$45

                    Pangea Suites$45
                    Best Vacation Home In Heart Of Downtown

                    Best Vacation Home In Heart Of Downtown

                    16 E Benton Ave, Naperville
                      3.0 out of 5.0
                       
                       

                      Best Vacation Home In Heart Of Downtown$83

                      Best Vacation Home In Heart Of Downtown$83
                      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

                      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$86

                        Palmer House a Hilton Hotel$86
                        Hyatt Regency Chicago

                        Hyatt Regency Chicago

                        151 East Wacker Dr, Chicago
                          4.0 out of 5.0
                           
                           

                          This Magnificent Mile hotel is located among Chicago's world-class shopping, restaurants and attractions. The Navy Pier, Millennium Park and Art Institute are ...

                          Hyatt Regency Chicago$119

                          Hyatt Regency Chicago$119
                          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$98

                            Embassy Suites Chicago Downtown Magnificent Mile$98
                            Freehand Chicago

                            Freehand Chicago

                            19 East Ohio Street, Chicago
                              3.5 out of 5.0
                               
                               

                              Located in River North, this hotel is within 6 mi (10 km) of Chinese Consulate, Holy Name Cathedral, and Museum of Contemporary Art. Water Tower Place and Ann ...

                              Freehand Chicago$69

                              Freehand Chicago$69