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Vacation Rentals in Chicago

See all Vacation Rentals in Chicago

Estimated price for 1 night/2 adults

Pittsfield Apartments + Suites

Pittsfield Apartments + Suites

55 E Washington St., Chicago, IL
    2.5 out of 5.0
     
     
    2.5 out of 5 (11 reviews)

    Located in The Loop, this aparthotel is steps from Chicago Cultural Center, Millennium Park, and Michigan Avenue. State Street and Cloud Gate are also within ...

    Pittsfield Apartments + Suites$80

    when booking Apr 23 - Apr 24

    Comfort Suites Michigan Avenue Loop

    Comfort Suites Michigan Avenue Loop

    320 N. Michigan Avenue, Chicago, IL
      3.0 out of 5.0
       
       
      4.4 out of 5 (41 reviews)

      Located in The Loop, this aparthotel is steps from Chicago Riverwalk and Michigan Avenue. Chicago Theatre and Millennium Park are also within 10 minutes. Randolph-Wabash ...

      Comfort Suites Michigan Avenue Loop$99

      when booking Apr 21 - Apr 22

      Dewitt Hotel and Suites

      Dewitt Hotel and Suites

      900 N Dewitt Pl, Chicago, IL
        3.0 out of 5.0
         
         
        3.8 out of 5 (10 reviews)

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

        Dewitt Hotel and Suites$80

        when booking Apr 21 - Apr 22

        Homewood Suites by Hilton Chicago Downtown South Loop

        Homewood Suites by Hilton Chicago Downtown South Loop

        59 E. 11th Street, Chicago, IL
          3.0 out of 5.0
           
           

          Located in The Loop, this aparthotel is within a 10-minute walk of State Street and Columbia College Chicago. Grant Park and Field Museum of Natural History ...

          Oakwood 200 Squared

          Oakwood 200 Squared

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

            Located in The Loop, this aparthotel is steps from Cadillac Palace Theatre and Chicago Riverwalk. Chicago Theatre and Merchandise Mart are also within 10 minutes. ...

            Newly Renovated 1200 Sq/ft Apartment. Sleeps 5

            Newly Renovated 1200 Sq/ft Apartment. Sleeps 5

            Elmwood Park, IL
               
               

              Situated in Elmwood Park, this historic vacation home is 2.9 mi (4.6 km) from Frank Lloyd Wright Home and Studio and within 6 mi (10 km) of Rosemont Theatre ...

              Newly Renovated 1200 Sq/ft Apartment. Sleeps 5$69

              when booking Apr 20 - Apr 21

              Residence Inn Marriott Chicago Midway

              Residence Inn Marriott Chicago Midway

              6638 S Cicero Ave, Chicago, IL
                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 Brookfield Zoo. State Street and Douglas Park are ...

                Residence Inn Marriott Chicago Midway$144

                when booking Apr 26 - Apr 27

                WoodSpring Suites Chicago Tinley Park

                WoodSpring Suites Chicago Tinley Park

                18636 West Creek Drive, Tinley Park, IL
                  2.5 out of 5.0
                   
                   
                  2.7 out of 5 (3 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

                  when booking Apr 20 - Apr 21

                  Residence Inn by Marriott Chicago Naperville/Warrenville

                  Residence Inn by Marriott Chicago Naperville/Warrenville

                  28500 Bella Vista Parkway, Warrenville, IL
                    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$88

                    when booking May 3 - May 4

                    Pangea Suites

                    Pangea Suites

                    55 E Washington Street, Chicago, IL
                      3.5 out of 5.0
                       
                       
                      2.0 out of 5 (3 reviews)

                      Located in The Loop, this aparthotel is steps from Chicago Cultural Center, Millennium Park, and Michigan Avenue. State Street and Cloud Gate are also within ...

                      Best Vacation Home In Heart Of Downtown

                      Best Vacation Home In Heart Of Downtown

                      16 E Benton Ave, Naperville, IL
                        3.0 out of 5.0
                         
                         

                        Best Vacation Home In Heart Of Downtown$143

                        when booking Apr 21 - Apr 22

                        House with 2 King Beds, 4K TV & Wifi

                        House with 2 King Beds, 4K TV & Wifi

                        22 W Franklin Ave, Naperville, IL
                          3.5 out of 5.0
                           
                           

                          Located in the heart of Naperville, this vacation home is within 9 mi (15 km) of Blackwell Forest Preserve, Morton Arboretum, and College of Dupage. Wheaton ...

                          Candlewood Suites Chicago/Naperville

                          Candlewood Suites Chicago/Naperville

                          27 W 300 Warrenville Rd, Warrenville, IL
                            3.0 out of 5.0
                             
                             
                            3.7 out of 5 (3 reviews)

                            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 ...

                            Candlewood Suites Chicago/Naperville$68

                            when booking Apr 27 - Apr 28

                            Private & Spacious Home in Chicago North Side Rogers Park Neighborhood

                            Private & Spacious Home in Chicago North Side Rogers Park Neighborhood

                            Chicago, IL
                               
                               

                              Located in Rogers Park, this historic vacation home is 1.1 mi (1.7 km) from Loyola University Chicago and 2.8 mi (4.4 km) from Aragon Entertainment Center. Northwestern ...

                              Private & Spacious Home in Chicago North Side Rogers Park Neighborhood$90

                              when booking Apr 23 - Apr 24

                              River North Waterside Condos 1BD

                              River North Waterside Condos 1BD

                              Chicago, IL
                                 
                                 

                                Located in River North, this apartment building is within a 10-minute walk of Merchandise Mart, Chicago Riverwalk, and State Street. House of Blues Chicago and ...

                                University of Chicago's Neighbor

                                University of Chicago's Neighbor

                                Chicago, IL
                                   
                                   

                                  Located in Woodlawn, this apartment building is within 1 mi (2 km) of University of Chicago Medicine, University of Chicago, and State Street. Chicago Museum ...

                                  Wrigleyville Unit - 1/2 Block From Wrigley Field - Sleeps 5

                                  Wrigleyville Unit - 1/2 Block From Wrigley Field - Sleeps 5

                                  Chicago, IL
                                     
                                     

                                    Located in Lakeview, this condo building is within 2 mi (3 km) of Wrigley Field, Vic Theatre, and Briar Street Theatre. Lincoln Park and DePaul University-Lincoln ...

                                    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.