Beginning of main content

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any vacation rental reservation


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
     
     
    3.0 out of 5 (599 reviews)

    Located in The Loop, this apartment building is steps from Chicago Cultural Center and Millennium Park. Art Institute of Chicago and Ford Center for the Performing ...

    Pittsfield Apartments + Suites$57

    Pittsfield Apartments + Suites$57
    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 (1,526 reviews)

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

      Comfort Suites Michigan Avenue Loop$99

      Comfort Suites Michigan Avenue Loop$99
      Celeste Celebrity Suites

      Celeste Celebrity Suites

      68 E Cedar St, Chicago
        4.0 out of 5.0
         
         
        4.5 out of 5 (32 reviews)

        Located in Gold Coast, this apartment building is within a 10-minute walk of John Hancock Center and Chicago Water Tower. Tribune Tower and Wrigley Building ...

        Celeste Celebrity Suites$199

        Celeste Celebrity Suites$199
        Ginosi Plymouth Apartel

        Ginosi Plymouth Apartel

        417 South Dearborn Street, Chicago
          3.5 out of 5.0
           
           
          3.7 out of 5 (24 reviews)

          This aparthotel is located in Chicago (The Loop), close to Roosevelt University, Art Institute of Chicago, and Willis Tower. Also nearby are Skydeck Ledge and ...

          Ginosi Plymouth Apartel$89

          Ginosi Plymouth Apartel$89
          Magnolia Coach House

          Magnolia Coach House

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

            Located in Edgewater, this apartment building is 1.1 mi (1.7 km) from Loyola University Chicago and within 3 mi (5 km) of Wrigley Field and Lincoln Park. Montrose ...

            Magnolia Coach House$160

            Magnolia Coach House$160
            Cozy Private Room in the of Pilsen - Chicago for Single Occupancy!

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

            , Chicago
               
               
              5.0 out of 5 (1 reviews)

              This vacation home is located in Canalport (Lower West Side), close to Douglas Park, University of Illinois Chicago, and United Center. Local attractions also ...

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

              Cozy Private Room in the of Pilsen - Chicago for Single Occupancy!Get Rates
              Furnished Suites Near Navy Pier

              Furnished Suites Near Navy Pier

              420 East Ohio Chicago, IL 60611, Chicago
                3.5 out of 5.0
                 
                 
                3.4 out of 5 (13 reviews)

                Located in Near North Side, this apartment building is within a 10-minute walk of Navy Pier and Chicago Children's Museum. Tribune Tower and Wrigley Building ...

                Furnished Suites Near Navy PierGet Rates

                Furnished Suites Near Navy PierGet Rates
                Extended Stay America - Chicago- O'Hare - Allstate Arena

                Extended Stay America - Chicago- O'Hare - Allstate Arena

                1207 E Touhy Ave, Des Plaines
                  2.5 out of 5.0
                   
                   
                  3.3 out of 5 (332 reviews)

                  Situated in Des Plaines, this aparthotel is 0.7 mi (1.1 km) from Allstate Arena and within 3 mi (5 km) of Rivers Casino and McDonald's Museum. Donald E. Stephens ...

                  Extended Stay America - Chicago- O'Hare - Allstate Arena$75

                  Extended Stay America - Chicago- O'Hare - Allstate Arena$75
                  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
                     
                     
                    3.0 out of 5 (4 reviews)

                    Located in Near South Side, this condo building is within a 15-minute walk of Columbia College Chicago and Grant Park. Art Institute of Chicago and Millennium ...

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

                    Chicago Downtown Condo - Michigan Ave Suite ID #14-15Get Rates
                    Extended Stay America Chicago - Romeoville

                    Extended Stay America Chicago - Romeoville

                    1225 Lakeview Dr, Romeoville
                      2.5 out of 5.0
                       
                       
                      3.3 out of 5 (212 reviews)

                      Situated in Romeoville, this aparthotel is 2 mi (3.2 km) from Bolingbrook Golf Club and within 6 mi (10 km) of Naperbrook Golf Course and Mistwood Golf Club. ...

                      Extended Stay America Chicago - Romeoville$63

                      Extended Stay America Chicago - Romeoville$63
                      1blk From Lake, Parking Included and More!

                      1blk From Lake, Parking Included and More!

                      , Chicago
                         
                         
                        5.0 out of 5 (1 reviews)

                        This property is located in Chicago (Edgewater), close to Montrose Beach, Wrigley Field, and Lincoln Park. Local attractions also include Loyola University Chicago ...

                        1blk From Lake, Parking Included and More!Get Rates

                        1blk From Lake, Parking Included and More!Get Rates
                        Chicago Luxurious Vintage Vacation Condo

                        Chicago Luxurious Vintage Vacation Condo

                        , Chicago
                           
                           
                          4.7 out of 5 (32 reviews)

                          This property is located in Chicago (Rogers Park), close to Loyola University Chicago and Northwestern University. Area attractions also include Wrigley Field ...

                          Chicago Luxurious Vintage Vacation CondoGet Rates

                          Chicago Luxurious Vintage Vacation CondoGet Rates
                          South Loop Luxury Lofts

                          South Loop Luxury Lofts

                          , Chicago
                             
                             

                            This vacation home is located in Canalport (McKinley Park), close to Guaranteed Rate Field, University of Illinois Chicago, and McCormick Place. Local attractions ...

                            South Loop Luxury LoftsGet Rates

                            South Loop Luxury LoftsGet Rates
                            Stay Alfred Apartments on Wabash

                            Stay Alfred Apartments on Wabash

                            1333 S. Wabash Avenue, Chicago
                               
                               
                              4.0 out of 5 (4 reviews)

                              This apartment building is located in Chicago (Near South Side), close to Field Museum of Natural History, Soldier Field, and John G. Shedd Aquarium. Also nearby ...

                              Stay Alfred Apartments on WabashGet Rates

                              Stay Alfred Apartments on WabashGet Rates
                              Extended Stay America Chicago - Vernon Hills - Lake Forest

                              Extended Stay America Chicago - Vernon Hills - Lake Forest

                              215 N Milwaukee Ave, Vernon Hills
                                2.5 out of 5.0
                                 
                                 
                                3.6 out of 5 (241 reviews)

                                Situated in Vernon Hills, this aparthotel is 1.6 mi (2.6 km) from Cuneo Mansion and Gardens and within 6 mi (10 km) of MainStreet Libertyville and Trinity International ...

                                Extended Stay America Chicago - Vernon Hills - Lake Forest$66

                                Extended Stay America Chicago - Vernon Hills - Lake Forest$66
                                Furnished Suites in South Loop Chicago

                                Furnished Suites in South Loop Chicago

                                1333 S Wabash Ave, Chicago
                                  3.5 out of 5.0
                                   
                                   
                                  3.9 out of 5 (20 reviews)

                                  Located in Near South Side, this apartment building is within 1 mi (2 km) of Columbia College Chicago, Art Institute of Chicago, and McCormick Place. Grant Park ...

                                  Furnished Suites in South Loop Chicago$250

                                  Furnished Suites in South Loop Chicago$250
                                  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
                                     
                                     
                                    5.0 out of 5 (3 reviews)

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

                                    Stunning 3BR in Lake View by SonderGet Rates

                                    Stunning 3BR in Lake View by SonderGet Rates
                                    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
                                       
                                       
                                      4.9 out of 5 (16 reviews)

                                      This property is located in Chicago (Gold Coast), close to John Hancock Center, Chicago Water Tower, and Millennium Park. Also nearby are Art Institute of Chicago ...

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

                                      Celeste Celebrity Theme Unit In Gold Coast. In 7 Unit Building Gold Coast!Get Rates
                                      Vibrant Studio in Gold Coast by Sonder

                                      Vibrant Studio in Gold Coast by Sonder

                                      East Bellevue Place and N Rush St, Chicago
                                         
                                         

                                        Located in Gold Coast, this apartment building is within a 10-minute walk of John Hancock Center and Chicago Water Tower. Tribune Tower and Wrigley Building ...

                                        Vibrant Studio in Gold Coast by SonderGet Rates

                                        Vibrant Studio in Gold Coast by SonderGet Rates
                                        Celeste Celebrity Suites Gold Coast!

                                        Celeste Celebrity Suites Gold Coast!

                                        , Chicago
                                           
                                           
                                          5.0 out of 5 (23 reviews)

                                          This property is located in Chicago (Gold Coast), close to John Hancock Center, Chicago Water Tower, and Millennium Park. Also nearby are Art Institute of Chicago ...

                                          Celeste Celebrity Suites Gold Coast!Get Rates

                                          Celeste Celebrity Suites Gold Coast!Get Rates
                                          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

                                          Central Loop Hotel

                                          Central Loop Hotel

                                          111 West Adams Street, Chicago
                                            4.0 out of 5.0
                                             
                                             

                                            Situated in the heart of "the Loop," the contemporary Central Loop Hotel is steps from all of Chicago’s major business and cultural destinations such as Chicago ...

                                            Central Loop Hotel$121

                                            Central Loop Hotel$121
                                            River Hotel

                                            River Hotel

                                            75 East Wacker Drive, Chicago
                                              4.0 out of 5.0
                                               
                                               

                                              Located in The Loop, this hotel is within a 10-minute walk of Chicago Theatre, Wrigley Building, and Tribune Tower. Ford Center for the Performing Arts Oriental ...

                                              River Hotel$117

                                              River Hotel$117
                                              The Whitehall Hotel

                                              The Whitehall Hotel

                                              105 E Delaware Pl, Chicago
                                                4.0 out of 5.0
                                                 
                                                 

                                                Built in 1927, this Chicago hotel is one block from Michigan Avenue shopping and Rush Street restaurants and nightlife; Lake Michigan is within five blocks.

                                                The Whitehall Hotel$101

                                                The Whitehall Hotel$101
                                                Wyndham Grand Chicago Riverfront

                                                Wyndham Grand Chicago Riverfront

                                                71 E Wacker Dr, Chicago
                                                  4.0 out of 5.0
                                                   
                                                   

                                                  This 39-story Chicago hotel is across the river from Magnificent Mile shopping, six blocks from Lake Michigan, and a half-mile from the Loop's theater district ...

                                                  Wyndham Grand Chicago Riverfront$119

                                                  Wyndham Grand Chicago Riverfront$119