check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Vacation Rentals in Chicago, Illinois (1,244)

  • 1 - 50 of 1,244
Additional fees apply. Taxes may be added.
    • 2 BR
    • 1 BA
    • Sleeps 4
    Apartment #856957vb
      • 1 BR
      • 1 BA
      • Sleeps 4
      Condo #4037980
        • 1 BR
        • 1 BA
        • Sleeps 3
        Apartment #836462vb
          • 3 BR
          • 2 BA
          • Sleeps 8
          Condo #939473
            • 3 BR
            • 2 BA
            • 1 HF BA
            • Sleeps 6
            Condo #4276593
              • 1 BR
              • 2 BA
              • Sleeps 2
              Apartment #864022vb
                • 1 BR
                • Sleeps 4
                Apartment #870614vb
                  • 1 BR
                  • 1 BA
                  • Sleeps 2
                  Condo #767984vb
                    • 1 BR
                    • 1 BA
                    • Sleeps 3
                    Apartment #836457vb
                      • 1 BR
                      • 1 BA
                      • Sleeps 4
                      Apartment #690239vb
                        • 1 BR
                        • 1 BA
                        • Sleeps 5
                        Apartment #870916vb
                          • 4 BR
                          • 2 BA
                          • Sleeps 10
                          Apartment #627209vb
                            • 3 BR
                            • 2 BA
                            • Sleeps 6
                            Townhome #3917584
                              • 3 BR
                              • 2 BA
                              • Sleeps 6
                              Condo #376151vb
                                • 4 BR
                                • 3 BA
                                • Sleeps 11
                                Apartment #889984vb
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 4
                                  Apartment #4263500
                                    • 3 BR
                                    • 1 BA
                                    • Sleeps 6
                                    Apartment #852515vb
                                      • 3 BR
                                      • 1 BA
                                      • Sleeps 5
                                      Apartment #600158vb
                                        • 3 BR
                                        • 1 BA
                                        • Sleeps 7
                                        Apartment #819226vb
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 4
                                          Apartment #3751630
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 6
                                            Apartment #852513vb
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 8
                                              Condo #708413vb
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 2
                                                House #4280611
                                                  • 6 BR
                                                  • 3 BA
                                                  • Sleeps 18
                                                  Condo #682966vb
                                                    • 4 BR
                                                    • 3 BA
                                                    • Sleeps 10
                                                    Barn #916963vb
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 8
                                                      Apartment #179389vb
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 3
                                                        Apartment #819227vb
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 5
                                                          Apartment #855043vb
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 2
                                                            Studio #916837vb
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              Studio #4276033
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 5
                                                                Apartment #784869vb
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 8
                                                                  Apartment #422128vb
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    Condo #296798
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      Apartment #865945vb
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        Apartment #470476vb
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 10
                                                                          Condo #400905vb
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 8
                                                                            Apartment #4307021
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              Apartment #408313vb
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Apartment #588228vb
                                                                                  • Studio
                                                                                  • 1 BA
                                                                                  • Sleeps 2
                                                                                  Apartment #742485vb
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 7
                                                                                    Apartment #4288310
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 2
                                                                                      Studio #4304772
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 3
                                                                                        Apartment #819209vb
                                                                                        • 1 - 50 of 1,244