Beginning of main content

Get 24/7 travel help, thanks to our Customer First Guarantee

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Vacation Rentals in Chicago

See all Vacation Rentals in Chicago
Pittsfield Apartments + Suites $70
Pittsfield Apartments + Suites

Pittsfield Apartments + Suites

55 E Washington St., Chicago, IL
     
    2.8
    of 5, from 15 reviews
    2.5 out of 5.0 Stars

    Located in The Loop, this aparthotel is steps from Chicago Cultural Center, Grant Park, and Millennium Park. Chicago Theatre and Michigan Avenue are also within 5 minutes. Madison-Wabash Station and Randolph-Wabash Station are within a 5-minute walk.

    WoodSpring Suites Chicago Tinley Park $60
    WoodSpring Suites Chicago Tinley Park

    WoodSpring Suites Chicago Tinley Park

    18636 West Creek Drive, Tinley Park, IL
       
      2.8
      of 5, from 6 reviews
      2.5 out of 5.0 Stars

      Situated in the business district, this aparthotel is 1 mi (1.7 km) from Tinley Park Convention Center and 2.9 mi (4.7 km) from Hollywood Casino Amphitheatre. Space Golf and Coyote Run Golf Course are also within 9 mi (15 km). Tinley Park 80th Avenue Station is 24 minutes by foot.

      Sonder - Coeval
      Sonder - Coeval

      Sonder - Coeval

      1419 South Wabash Avenue, Chicago, IL
         
        4.0 out of 5.0 Stars

        Located in South Loop, this aparthotel is within a 10-minute walk of State Street and Grant Park. Field Museum of Natural History and John G. Shedd Aquarium are also within 1 mi (2 km). Roosevelt Station is 6 minutes by foot and Chicago Museum Campus-11th Street Station is 12 minutes.

        LEVEL Chicago – Old Town $149
        LEVEL Chicago – Old Town

        LEVEL Chicago – Old Town

        1140 North Wells Street, Chicago, IL
           
          4.0 out of 5.0 Stars

          Located in River North, this family-friendly Chicago aparthotel is within a 10-minute walk of Newberry Library and State Street. Second City and Michigan Avenue are also within 15 minutes. Clark-Division Station is only a 4-minute walk and Chicago Station (Brown Line) is 11 minutes.

          WoodSpring Suites Chicago Addison $59
          WoodSpring Suites Chicago Addison

          WoodSpring Suites Chicago Addison

          991 E. Lake Street, Addison, IL
             
            2.8
            of 5, from 5 reviews
            2.0 out of 5.0 Stars

            Located in the heart of Addison, this aparthotel is 3.1 mi (5 km) from Bloomingdale Golf Club and within 6 mi (10 km) of Odeum Sports and Expo Center and Adventist GlenOaks Hospital. Lilacia Park and Ned Brown Forest Preserve are also within 6 mi (10 km).

            Comfort Suites Michigan Avenue Loop
            Comfort Suites Michigan Avenue Loop

            Comfort Suites Michigan Avenue Loop

            320 N. Michigan Avenue, Chicago, IL
               
              4.4
              of 5, from 46 reviews
              3.0 out of 5.0 Stars

              Located in The Loop, this aparthotel is steps from Chicago Riverwalk and Michigan Avenue. Grant Park and Chicago Theatre are also within 5 minutes. Millennium Station is only a 5-minute walk and State Station is 6 minutes.

              Candlewood Suites Chicago/Naperville $64
              Candlewood Suites Chicago/Naperville

              Candlewood Suites Chicago/Naperville

              27 W 300 Warrenville Rd, Warrenville, IL
                 
                4.2
                of 5, from 6 reviews
                3.0 out of 5.0 Stars

                Situated in Warrenville, this apartment building is within 3 mi (5 km) of Blackwell Forest Preserve, Arrowhead Golf Club, and DuPage Children's Museum. Morton Arboretum and Wheaton College are also within 6 mi (10 km).

                Residence Inn by Marriott Chicago Naperville/Warrenville $93
                Residence Inn by Marriott Chicago Naperville/Warrenville

                Residence Inn by Marriott Chicago Naperville/Warrenville

                28500 Bella Vista Parkway, Warrenville, IL
                   
                  4.6
                  of 5, from 5 reviews
                  3.0 out of 5.0 Stars

                  Situated in the business district, this aparthotel is within 9 mi (15 km) of Morton Arboretum, Wheaton College, and College of Dupage. Chicago Premium Outlets and Hollywood Casino are also within 12 mi (20 km).

                  Sonder - The Plymouth $93
                  Sonder - The Plymouth

                  Sonder - The Plymouth

                  South Dearborn Street, Van Buren, Chicago, IL
                     
                    3.5 out of 5.0 Stars

                    Located in The Loop, this aparthotel is within a 10-minute walk of State Street, Grant Park, and Willis Tower. Art Institute of Chicago and Columbia College Chicago are also within 10 minutes. Harold Washington Library Station and LaSalle Street Station are within a 5-minute walk.

                    Residence Inn Marriott Chicago Midway $143
                    Residence Inn Marriott Chicago Midway

                    Residence Inn Marriott Chicago Midway

                    6638 S Cicero Ave, Chicago, IL
                       
                      4.8
                      of 5, from 8 reviews
                      3.0 out of 5.0 Stars

                      Situated near the airport, this aparthotel is within 9 mi (15 km) of SeatGeek Stadium, University of Chicago, and Brookfield Zoo. State Street and Douglas Park are also within 9 mi (15 km). Midway Station is 27 minutes by foot.

                      Ginosi 747 Apartel $62
                      Ginosi 747 Apartel

                      Ginosi 747 Apartel

                      747 N May St., Chicago, IL
                         
                        2.5 out of 5.0 Stars

                        Located in West Town, this aparthotel is within 2 mi (3 km) of Union Park, United Center, and Chicago Riverwalk. Water Tower Place and John Hancock Center are also within 2 mi (3 km). Chicago Station (Blue Line) is only a 2-minute walk and Grand Station (Blue Line) is 11 minutes.

                        Phenomenal 1 Bedroom Streeterville Condo
                        Phenomenal 1 Bedroom Streeterville Condo

                        Phenomenal 1 Bedroom Streeterville Condo

                        Chicago, IL
                           
                          0.0 out of 5.0 Stars

                          Located in Near North Side, this condo building is within a 10-minute walk of Michigan Avenue, Chicago Riverwalk, and Northwestern Memorial Hospital. Grant Park and Navy Pier are also within 15 minutes. Grand Station (Red Line) is 10 minutes by foot and Chicago Station (Red Line) is 16 minutes.

                          Welcome to Our Happy Home
                          Welcome to Our Happy Home

                          Welcome to Our Happy Home

                          Chicago, IL
                             
                            0.0 out of 5.0 Stars

                            Located in Washington Park, this vacation home is within 3 mi (5 km) of State Street, University of Chicago, and Chicago Museum of Science and Industry. University of Chicago Medicine and Robie House are also within 3 mi (5 km). Garfield Station (Red Line) is 5 minutes by foot and Garfield Station (Green Line) is 10 minutes.

                            The Seneca Just Blocks From Lake Michigan $70
                            The Seneca Just Blocks From Lake Michigan

                            The Seneca Just Blocks From Lake Michigan

                            Chicago, IL
                               
                              0.0 out of 5.0 Stars

                              Located in Near North Side, this condo building is within a 5-minute walk of Broadway Playhouse, Water Tower Place, and John Hancock Center. Michigan Avenue and Chicago Water Tower are also within 5 minutes. Chicago Station (Red Line) is 9 minutes by foot and Grand Station (Red Line) is 15 minutes.

                              Beautiful Vintage Loft in the Heart of Hyde Park $120
                              Beautiful Vintage Loft in the Heart of Hyde Park

                              Beautiful Vintage Loft in the Heart of Hyde Park

                              Chicago, IL
                                 
                                0.0 out of 5.0 Stars

                                Located in Kenwood, this apartment building is within 1 mi (2 km) of Burnham Park and University of Chicago. Chicago Museum of Science and Industry and State Street are also within 3 mi (5 km). 51st Station is 18 minutes by foot and Garfield Station (Green Line) is 22 minutes.

                                Stylish, Modern 3/1 APT .3 Miles From Lincoln SQ! -goathote $37
                                Stylish, Modern 3/1 APT .3 Miles From Lincoln SQ! -goathote

                                Stylish, Modern 3/1 APT .3 Miles From Lincoln SQ! -goathote

                                Chicago, IL
                                   
                                  0.0 out of 5.0 Stars

                                  Located in Ravenswood, this apartment building is 2.1 mi (3.3 km) from Aragon Entertainment Center and 3.1 mi (5 km) from Wrigley Field. Loyola University Chicago and Lincoln Park Zoo are also within 6 mi (10 km). Western Station (Brown Line) is 11 minutes by foot and Rockwell Station is 16 minutes.

                                  Cozy Condo Sleeps 5, Mins From O'hare/rosemont.. $53
                                  Cozy Condo Sleeps 5, Mins From O'hare/rosemont..

                                  Cozy Condo Sleeps 5, Mins From O'hare/rosemont..

                                  Chicago, IL
                                     
                                    0.0 out of 5.0 Stars

                                    Situated in Chicago, this apartment building is within 6 mi (10 km) of Portage Park, Rosemont Theatre, and Rivers Casino. Donald E. Stephens Convention Center and Fashion Outlets of Chicago are also within 6 mi (10 km). Harlem-O'Hare Station is 15 minutes by foot.

                                    Nice and Cozy Aptartment in two Unit Building. 20min From the Airport. Sleeps 5!
                                    Nice and Cozy Aptartment in two Unit Building. 20min From the Airport. Sleeps 5!

                                    Nice and Cozy Aptartment in two Unit Building. 20min From the Airport. Sleeps 5!

                                    Chicago, IL
                                       
                                      0.0 out of 5.0 Stars

                                      Located in Dunning, this apartment building is 1.9 mi (3.1 km) from Portage Park and within 6 mi (10 km) of Frank Lloyd Wright Home and Studio and Ernest Hemingway Museum and House. Concord Music Hall and Humboldt Park are also within 6 mi (10 km).

                                      Domio Navy Pier Convenient 2br/2ba + Fitness Center $101
                                      Domio Navy Pier Convenient 2br/2ba + Fitness Center

                                      Domio Navy Pier Convenient 2br/2ba + Fitness Center

                                      Chicago, IL
                                         
                                        0.0 out of 5.0 Stars

                                        Located in Near North Side, this apartment building is within a 10-minute walk of Lakefront Trail, Grant Park, and Navy Pier. Chicago Riverwalk and Chicago Children's Museum are also within 10 minutes. Grand Station (Red Line) is 13 minutes by foot and State Station is 18 minutes.

                                        The Estates Executive W/office Desk, Pvtbath & More $44
                                        The Estates Executive W/office Desk, Pvtbath & More

                                        The Estates Executive W/office Desk, Pvtbath & More

                                        Hoffman Estates, IL
                                           
                                          0.0 out of 5.0 Stars

                                          Situated in Hoffman Estates, this romantic vacation home is within 3 mi (5 km) of Schaumburg Medieval Times, Bridges of Poplar Creek Country Club, and The Water Works Indoor Water Park. Harper College is 3.1 mi (4.9 km) away.

                                          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.


                                          *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.