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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
     
     
    2.4 out of 5 (10 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

    Comfort Suites Michigan Avenue Loop

    Comfort Suites Michigan Avenue Loop

    320 N. Michigan Avenue, Chicago
      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. Art Institute of Chicago and Chicago Theatre are also within 6 mi (10 ...

      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
         
         
        3.7 out of 5 (9 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

        Residence Inn Marriott Chicago Midway

        Residence Inn Marriott Chicago Midway

        6638 S Cicero Ave, Chicago
          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 State Street. Douglas Park and University of Chicago ...

          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
             
             
            3.0 out of 5 (2 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

            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
               
               
              4.5 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$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 Garden Level Room

                Beautiful Garden Level Room

                Chicago
                   
                   

                  Beautiful Garden Level Room$30

                  Pangea Suites

                  Pangea Suites

                  55 E Washington Street, Chicago
                    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 and Millennium Park. Art Institute of Chicago and Chicago Riverwalk are also within ...

                    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

                      Modern Studio Wifi + Gym Downtown by Lyric

                      Modern Studio Wifi + Gym Downtown by Lyric

                      1 East Delaware Place, Chicago
                        3.5 out of 5.0
                         
                         

                        Located in Near North Side, this apartment building is 0.1 mi (0.1 km) from State Street.

                        House with 2 King Beds, 4K TV & Wifi

                        House with 2 King Beds, 4K TV & Wifi

                        22 W Franklin Ave, Naperville
                          3.5 out of 5.0
                           
                           

                          Situated in the city center, this vacation home is in the same area as Morton Arboretum, Blackwell Forest Preserve, and College of Dupage. Regional attractions ...

                          Celeste Celebrity Themed Unit In Gold Coast. In 7 Unit Building Gold Coast!

                          Celeste Celebrity Themed Unit In Gold Coast. In 7 Unit Building Gold Coast!

                          Chicago
                             
                             

                            Located in Near North Side, this historic property is within 6 mi (10 km) of Michigan Avenue, John Hancock Center, and Water Tower Place. Chicago Riverwalk and ...

                            Celeste Celebrity Themed Unit In Gold Coast. In 7 Unit Building Gold Coast!$199

                            Al Capone Unit In Beautiful Vintage Building In The Gold Coast!

                            Al Capone Unit In Beautiful Vintage Building In The Gold Coast!

                            Chicago
                               
                               

                              Located in Near North Side, this historic property is within 6 mi (10 km) of Michigan Avenue, John Hancock Center, and Water Tower Place. Chicago Riverwalk and ...

                              Celeste Celebrity Theme Unit In Gold Coast. In 7 Unit Building Gold Coast!

                              Celeste Celebrity Theme Unit In Gold Coast. In 7 Unit Building Gold Coast!

                              Chicago
                                 
                                 

                                Located in Near North Side, this historic property is within 6 mi (10 km) of Michigan Avenue, John Hancock Center, and Water Tower Place. Chicago Riverwalk and ...

                                Celeste Celebrity Theme Unit In Gold Coast. In 7 Unit Building Gold Coast!$129

                                Beautifully Rehabbed House in Brookfield -16 Miles From Downtown Chicago

                                Beautifully Rehabbed House in Brookfield -16 Miles From Downtown Chicago

                                Brookfield
                                   
                                   

                                  Situated in La Grange Park, this vacation home is close to Brookfield Zoo. Area attractions also include Toyota Park and Oakbrook Center Mall.

                                  Beautifully Rehabbed House in Brookfield -16 Miles From Downtown Chicago$50

                                  747 Zenith Apartment

                                  747 Zenith Apartment

                                  Chicago
                                     
                                     

                                    This property is located in Chicago (West Town), close to Merchandise Mart, United Center, and Willis Tower. Also nearby are Chicago Theatre and Water Tower ...

                                    747 Zenith Apartment$42

                                    Cozy Home in Chicago, Rogers Park Neighborhood

                                    Cozy Home in Chicago, Rogers Park Neighborhood

                                    Chicago
                                       
                                       

                                      This apartment building is located in Chicago (Rogers Park), close to Loyola University Chicago and Aragon Entertainment Center. Area attractions also include ...

                                      Special 30% off ! Free Parking 15 min Ord/downtown2

                                      Special 30% off ! Free Parking 15 min Ord/downtown2

                                      Chicago
                                         
                                         

                                        This apartment building is located in Chicago (Jefferson Park), close to Portage Park. Area attractions also include Donald E. Stephens Convention Center and ...

                                        Amazing Loft W/ Balcony 1

                                        Amazing Loft W/ Balcony 1

                                        Chicago
                                           
                                           

                                          Located in Uptown, this property is within 6 mi (10 km) of Aragon Entertainment Center, Wrigley Field, and Loyola University Chicago. Lincoln Park Zoo and John ...

                                          Amazing Loft W/ Balcony 1$50

                                          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.