Beginning of main content

If you find a lower price, we'll match it and refund the difference.

Update plans with no change or cancel fees from Travelocity.

Search over 400 airlines and more than 321,000 hotels worldwide.


Vacation Rentals in Chicago

See all Vacation Rentals in Chicago
Comfort Suites Michigan Avenue Loop

Comfort Suites Michigan Avenue Loop

320 N. Michigan Avenue, Chicago
    3.0 out of 5.0
     
     
    4.5 out of 5 (33 reviews)

    Located in The Loop, this aparthotel is within a 5-minute walk of Downtown Chicago and Wrigley Building. Millennium Park and Tribune Tower are also within 10 ...

    Comfort Suites Michigan Avenue Loop$129

    Comfort Suites Michigan Avenue Loop$129
    Chicago Guest House on Newport Avenue

    Chicago Guest House on Newport Avenue

    1216 W Newport Avenue, Chicago
      4.0 out of 5.0
       
       

      Located in Lakeview, this apartment building is within 1 mi (2 km) of Vic Theatre and Wrigley Field. Lincoln Park and Lincoln Park Zoo are also within 3 mi (5 ...

      Ginosi 747 Apartel

      Ginosi 747 Apartel

      747 N May St., Chicago
        2.5 out of 5.0
         
         

        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$108

        Ginosi 747 Apartel$108
        Oakwood 200 Squared

        Oakwood 200 Squared

        210 North Wells Street, Chicago
          4.0 out of 5.0
           
           

          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 ...

          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, Brookfield Zoo, and State Street. Douglas Park and University of Chicago Medicine ...

            Residence Inn Marriott Chicago Midway$165

            Residence Inn Marriott Chicago Midway$165
            Magnolia Coach House

            Magnolia Coach House

            5705 N Magnolia Ave, Chicago
              3.5 out of 5.0
               
               
              5.0 out of 5 (1 reviews)

              Located in Edgewater, this apartment building is 1.1 mi (1.7 km) from Loyola University Chicago and 2.8 mi (4.5 km) from Wrigley Field. Swedish Covenant Hospital ...

              Magnolia Coach House$171

              Magnolia Coach House$171
              Cozy Private Room in the of Pilsen - Chicago for Single Occupancy!

              Cozy Private Room in the of Pilsen - Chicago for Single Occupancy!

              , Chicago
                 
                 

                Located in Lower West Side, this historic vacation home is within 3 mi (5 km) of Douglas Park, University of Illinois Chicago, and United Center. Union Park ...

                Beautifulspalike Suite-northside-freewifi-grill-bikes-close to Wrigley&lakefront

                Beautifulspalike Suite-northside-freewifi-grill-bikes-close to Wrigley&lakefront

                , Chicago
                   
                   

                  Located in North Center, this apartment building is within 3 mi (5 km) of Swedish Covenant Hospital, Wrigley Field, and Lincoln Park. Vic Theatre and Concord ...

                  Chicago Downtown Condo - Michigan Ave Suite ID #14-15

                  Chicago Downtown Condo - Michigan Ave Suite ID #14-15

                  1255 S. Michigan Avenue, Chicago
                    2.5 out of 5.0
                     
                     

                    Located in South Loop, this condo building is within a 15-minute walk of Downtown Chicago and Grant Park. Art Institute of Chicago and Millennium Park are also ...

                    Furnished Suites in South Loop Chicago

                    Furnished Suites in South Loop Chicago

                    1333 S Wabash Ave, Chicago
                      3.5 out of 5.0
                       
                       
                      3.0 out of 5 (1 reviews)

                      Located in South Loop, this apartment building is within 1 mi (2 km) of Downtown Chicago, Art Institute of Chicago, and Grant Park. Field Museum of Natural History ...

                      Furnished Suites in South Loop Chicago$279

                      Furnished Suites in South Loop Chicago$279
                      Apartment in River North with Balcony

                      Apartment in River North with Balcony

                      750 North Hudson Avenue, Chicago
                        3.5 out of 5.0
                         
                         

                        Located in Near North Side, this apartment building is within 1 mi (2 km) of Downtown Chicago, John Hancock Center, and Merchandise Mart. Willis Tower and Skydeck ...

                        Perfect Location! Perfect Price! Includes Breakfast and Parking, Perfect for all

                        Perfect Location! Perfect Price! Includes Breakfast and Parking, Perfect for all

                        , Elmwood Park
                           
                           

                          Located in the heart of Elmwood Park, this historic apartment building is within 9 mi (15 km) of Rosemont Theatre, Brookfield Zoo, and Fashion Outlets of Chicago. ...

                          Family Friendly, 3bd, Irving Park, Chicago

                          Family Friendly, 3bd, Irving Park, Chicago

                          , Chicago
                             
                             

                            Set in the center of Chicago, this family-friendly apartment building is 2 mi (3.2 km) from Swedish Covenant Hospital, and within 6 mi (10 km) of Lincoln Park ...

                            Stunning 3BR in Lake View by Sonder

                            Stunning 3BR in Lake View by Sonder

                            West Barry Avenue and N Lakewood Ave, Chicago
                              4.0 out of 5.0
                               
                               

                              Located in Lakeview, this apartment building is within 1 mi (2 km) of Vic Theatre and Wrigley Field. Lincoln Park and Lincoln Park Zoo are also within 3 mi (5 ...

                              State and Grand by BridgeStreet

                              State and Grand by BridgeStreet

                              505 N State Street, Chicago
                                4.0 out of 5.0
                                 
                                 
                                5.0 out of 5 (1 reviews)

                                Located in Near North Side, this aparthotel is within a 10-minute walk of Downtown Chicago, Wrigley Building, and Tribune Tower. John Hancock Center and Chicago ...

                                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 spa apartment building is within a 10-minute walk of Downtown Chicago, John Hancock Center, and Chicago Water Tower. Tribune ...

                                  Artsy + Hip + Efficient in Beautiful Logan Square

                                  Artsy + Hip + Efficient in Beautiful Logan Square

                                  , Chicago
                                     
                                     

                                    Located in the heart of Chicago, this historic condo building is 1.8 mi (2.9 km) from Concord Music Hall and 2.5 mi (4 km) from Humboldt Park. Wrigley Field ...

                                    Serene Home Close to City, Wifi, Bicycles, Grill, Toys and Games

                                    Serene Home Close to City, Wifi, Bicycles, Grill, Toys and Games

                                    , Lombard
                                       
                                       

                                      Situated in Lombard, this vacation home is within 3 mi (5 km) of Yorktown Shopping Center, Oakbrook Center Mall, and Drury Lane Theater. Lilacia Park and York ...

                                      Vibrant 2BR in Wrigleyville by Sonder

                                      Vibrant 2BR in Wrigleyville by Sonder

                                      North Southport Avenue and W Waveland Av, Chicago
                                        4.0 out of 5.0
                                         
                                         

                                        Located in Lakeview, this apartment building is within 1 mi (2 km) of Vic Theatre and Wrigley Field. Lincoln Park and Lincoln Park Zoo are also within 3 mi (5 ...

                                        Mid-Century 2BR in Lincoln Park by Sonder

                                        Mid-Century 2BR in Lincoln Park by Sonder

                                        N Halsted St., Chicago
                                          4.0 out of 5.0
                                           
                                           

                                          Located in Lincoln Park, this apartment building is within 2 mi (3 km) of Kingston Mines, Wrigley Field, and Lincoln Park Zoo. John Hancock Center and 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.